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1

DANSHPAJUH, Marjan, and Neda HASANZADEH. "Study of influence of anomeric effect on conformational preferences using hybrid density functional theory (DFT) and natural bond orbital (NBO) interpretation." Revue Roumaine de Chimie 68, no. 1-2 (2023): 61–74. http://dx.doi.org/10.33224/rrch.2023.68.1-2.06.

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For the relationship between thermodynamic parameters, global hardness, global electronegativity, anomeric effect, structural parameters, and structural properties of dodecahedro-spiro [isochromene-3,2'-pyran] (A), dodecahedro-spiro [isothiocromene-3,2'- thiopyran) (B), dodecahedro-spiro [isochroman-3,2'-thiopyran] (C) and dodecahedro-spiro [isothiochrome-3,2'-pyran] (D) computational methods (B3LYP / 6-311 ++ G **) were used. Results show that the calculated Gibbs free energy and enthalpy differences between the axial- and equatorial- stereoisomers [i.e. ΔG = Geq – Gax, ΔH = Heq- Hax] decreas
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2

Tripathi, Rahul R., and Ratnamala P. Sonawane. "An Extraction of the Isatin from the Couroupita guianesis (Cannon Ball Tree) and a Novel Synthesis of the N,N'-(2-oxo-3'H-spiro[indoline-3,2'-[1,3,4]thiadiazole]-3',5'-diyl]diacetamidefrom the Isatin." International Letters of Chemistry, Physics and Astronomy 15 (September 2013): 119–25. http://dx.doi.org/10.18052/www.scipress.com/ilcpa.15.119.

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Isatins are synthetically versatile substrates, where they can be used for the synthesis of a large variety of Isatins and heterocyclic compounds. In this, the isatin were extracted from the floral material of Couroupita guianesis commonly known as an Cannon ball tree. After that, a novel heterocyclic spiro derivative having an IUPAC name N,N’-(2-oxo-3’H-spiro[indoline-3,2’-[1,3,4] thiadiazole]-3’5’-diyl)diacetamide were synthesized , which may be used as raw material for drug synthesis. A spiro compound N,N’-(2-oxo-3’H-spiro[indoline-3,2’-[1,3,4] thiadiazole]-3’5’-diyl)diacetamide were synthe
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3

Tripathi, Rahul R., and Ratnamala P. Sonawane. "An Extraction of the Isatin from the <i>Couroupita guianesis</i> (Cannon Ball Tree) and a Novel Synthesis of the N,N'-(2-oxo-3'H-spiro[indoline-3,2'-[1,3,4]thiadiazole]-3',5'-diyl]diacetamidefrom the Isatin." International Letters of Chemistry, Physics and Astronomy 15 (June 29, 2013): 119–25. http://dx.doi.org/10.56431/p-h7k957.

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Isatins are synthetically versatile substrates, where they can be used for the synthesis of a large variety of Isatins and heterocyclic compounds. In this, the isatin were extracted from the floral material of Couroupita guianesis commonly known as an Cannon ball tree. After that, a novel heterocyclic spiro derivative having an IUPAC name N,N’-(2-oxo-3’H-spiro[indoline-3,2’-[1,3,4] thiadiazole]-3’5’-diyl)diacetamide were synthesized , which may be used as raw material for drug synthesis. A spiro compound N,N’-(2-oxo-3’H-spiro[indoline-3,2’-[1,3,4] thiadiazole]-3’5’-diyl)diacetamide were synthe
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4

Hafez, Hend N., Abdel-Rhman B. A. El-Gazzar, and Magdi E. A. Zaki. "Simple approach to thieno[3,2-d]pyrimidines as new scaffolds of antimicrobial activities." Acta Pharmaceutica 66, no. 3 (2016): 331–51. http://dx.doi.org/10.1515/acph-2016-0029.

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Abstract 6ʹ-(4-Chlorophenyl)-spiro[cyclohexane-1,2ʹ-thieno[3,2-d][1,3] oxazin]-4ʹ(1ʹH)-one (1) was synthesized and used as a starting material for the synthesis of a novel series of spiro compounds having biologically active sulfonamide 2a-e and 3ʹ-(4-acetylphenyl)-6ʹ- (4-chlorophenyl)-1ʹH-spiro[cyclohexane-1,2ʹ-thieno[3,2-d] pyrimidine-4ʹ(3ʹH)-one (3). Compound 2a was used as a key intermediate for the synthesis of sulfonyl carbothioamide derivatives 4a-c. Also, compound 3 was used as an intermediate for the synthesis of 3ʹH-spiro[cyclohexane-1,2ʹ-thieno[3,2-d]pyrimidin]-3ʹ-yl] phenyl}-2-imin
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5

Macháček, Vladimír, Makky M. M. Hassanien, and Vojeslav Štěrba. "Kinetics and mechanism of spiro adduct formation from and smiles rearrangement of N-methyl-N-(2,4,6-trinitrophenyl)aminoacetanilide. Base-catalyzed transformation of N-(2,4,6-trinitrophenylamino)acetanilide into 2-nitroso-4,6-dinitroaniline." Collection of Czechoslovak Chemical Communications 52, no. 9 (1987): 2225–40. http://dx.doi.org/10.1135/cccc19872225.

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The paper deals with kinetics and mechanism of the reaction of N-(2,4,6-trinitrophenyl)aminoacetanilide (IIa) with methoxide ion and with the reaction kinetics and product structure of the reaction of N-methyl-N-(2,4,6-trinitrophenyl)aminoacetanilide (IIb) in methanolic buffers. The main product of the reaction of compound IIa with methoxide is 2-nitroso-4,6-dinitroaniline along with about 3% spiro adduct. The dependence of the experimental rate constant kexp of the reaction with methoxide on the methoxide concentration is similar to that of the reaction of N-(2,4,6-trinitrophenyl)glycine meth
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6

KRISHNA, C. JOSHI, DANOIA ANSHU, S. SHARMA C., and JOSHI RAHUL. "Investigation of the Reaction of Fluorine containing 1,3-Dihydro-3-( 1 ,5-dihydro-3-methyl-5-oxo-1-phenyl-4Hpyrazol- 4-ylidene )-2H-indol-2-one with Hydrazine Derivatives." Journal of Indian Chemical Society Vol. 71, June-Aug 1994 (1994): 459–62. https://doi.org/10.5281/zenodo.5895738.

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<em>Department of Chemistry. University of Rajasthan, Jaipur-302 004 Manuscript received 1 December 1993</em> The reaction of 1,3-dihydro-3-(1,5-dihydro-3-methyl-5-oxo-1-phenyl-4<em>H</em>-pyrazol-4-ylldene)-2<em>H</em>-indo 1-2-ones (3a-d) with various hydrazines has&nbsp;been studied in the absolute ethanol/glacial acetic acid medium. Reaction of 3a-c with phenyl hydrazine in absolute ethanol gave exclusively spiro compounds (64-76%), while in glacial acetic acid, a mixture of spiro compound (18-&#39;7%), hydrazones (14-25%) and a condensed compound (22-33%) was formed. 3 however gave only t
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7

Rani, U. Usha, and A. Sreedevi. "Synthesis and Biological Evaluation of 3-(2-Benzoyl-4-chlorophenyl)-4H-spiro [indole-3,2-[1,3]thiazolidine]-2,4(1H)- dione Derivatives for Anti-tubercular and Antimicrobial Activities." Indian Journal Of Science And Technology 17, no. 20 (2024): 2101–9. http://dx.doi.org/10.17485/ijst/v17i20.1434.

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Objectives: To synthesize a new scaff fold of 3'-(2-Benzoyl-4-chlorophenyl)-4'H-spiro [indole-3,2'-[1,3] thiazolidine]-2,4'(1H)-dione derivatives and to assess the compounds for anti-tubercular and antimicrobial activities. Methods : A new series of 3'-(2-Benzoyl-4-chlorophenyl)-4'H-spiro [indole-3,2'- [1,3] thiazolidine]-2,4'(1H)-dione derivatives were prepared by synthesizing schiff’s bases followed by condensing schiff base with 2-mercaptopropanoic acid in the presence of zinc chloride. Synthesized compounds were characterized by IR, NMR and Mass spectral data. Their antimicrobial, antitube
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8

Nakano, Koji, Ko Takase, and Keiichi Noguchi. "Furan-Containing Chiral Spiro-Fused Polycyclic Aromatic Compounds: Synthesis and Photophysical Properties." Molecules 27, no. 16 (2022): 5103. http://dx.doi.org/10.3390/molecules27165103.

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Spiro-fused polycyclic aromatic compounds (PACs) have received growing interest as rigid chiral scaffolds. However, furan-containing spiro-fused PACs have been quite limited. Here, we design spiro[indeno[1,2-b][1]benzofuran-10,10′-indeno[1,2-b][1]benzothiophene] as a new family of spiro-fused PACs that contain a furan unit. The compound was successfully synthesized in enantiopure form and also transformed to its S,S-dioxide derivative and the pyrrole-containing analog via aromatic metamorphosis. The absorption and emission properties of the obtained furan-containing chiral spiro-fused PACs are
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9

Konyar, Dilan, Cenk A. Andac, and Erdem Buyukbingol. "Design, Synthesis and Cytotoxic Activity of Spiro(oxindole-3-3'- pyrrolidine) Derivatives." Letters in Drug Design & Discovery 15, no. 1 (2018): 37–45. http://dx.doi.org/10.2174/1570180814666170810120634.

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Background: Spiro[pyrrolidine-3,3'-oxindole] compounds are reported to be highly bioactive natural and synthetic products. Initially, spirooxindole alkaloids were isolated from plants of the Apocynaceae and Rubiaceae families, which were found to have a common scaffold, spiro[pyrrolidine-3,3'-oxindole], exhibiting anticancer activities., we specifically aimed at the synthesis, characterization and anticancer activity of novel spiro[pyrrolidine-3,3' -oxindole] derivatives, compounds 6a-c and 7. Methods: The synthesis was initiated by Knovenegal condensation of indole-2-one with an appropriate b
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10

U, Usha Rani, and Sreedevi A. "Synthesis and Biological Evaluation of 3-(2-Benzoyl-4-chlorophenyl)-4H-spiro [indole-3,2-[1,3]thiazolidine]-2,4(1H)- dione Derivatives for Anti-tubercular and Antimicrobial Activities." Indian Journal of Science and Technology 17, no. 20 (2024): 2101–9. https://doi.org/10.17485/IJST/v17i20.1434.

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Abstract <strong>Objectives:</strong>&nbsp;To synthesize a new scaff fold of 3'-(2-Benzoyl-4-chlorophenyl)-4'H-spiro [indole-3,2'-[1,3] thiazolidine]-2,4'(1H)-dione derivatives and to assess the compounds for anti-tubercular and antimicrobial activities.&nbsp;<strong>Methods :</strong>&nbsp;A new series of 3'-(2-Benzoyl-4-chlorophenyl)-4'H-spiro [indole-3,2'- [1,3] thiazolidine]-2,4'(1H)-dione derivatives were prepared by synthesizing schiff&rsquo;s bases followed by condensing schiff base with 2-mercaptopropanoic acid in the presence of zinc chloride. Synthesized compounds were characterized
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11

Barakat, Assem, Mohammad Shahidul Islam, M. Ali, et al. "Regio- and Stereoselective Synthesis of a New Series of Spirooxindole Pyrrolidine Grafted Thiochromene Scaffolds as Potential Anticancer Agents." Symmetry 13, no. 8 (2021): 1426. http://dx.doi.org/10.3390/sym13081426.

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A series of new spiro-heterocycles engrafted spirooxindole/pyrrolidine/thiochromene scaffolds was synthesized by the three-component 1,3-dipolar cycloaddition reactions in a fully controlled regio- and stereo-selective fashion. Condensation of several substituted isatin derivatives with L-proline generated the azomethine ylides which subsequently reacted with chalcones based thiochromene scaffold, and finally afforded the target spiro-compounds. This simple protocol furnished a structurally complex, biologically relevant spiro-heterocycles in good yields through a one-pot process. All synthesi
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12

Westphal, Regina, Eclair Venturini Filho, Laiza Bruzadelle Loureiro, et al. "Green Synthesis of Spiro Compounds with Potential Anticancer Activity through Knoevenagel/Michael/Cyclization Multicomponent Domino Reactions Organocatalyzed by Ionic Liquid and Microwave-Assisted." Molecules 27, no. 22 (2022): 8051. http://dx.doi.org/10.3390/molecules27228051.

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In this work a microwave-assisted Knoevenagel/Michael/cyclization multicomponent domino methodology, using ethanol as solvent and the ionic liquid 1-methylimidazolium chloride as catalyst was developed for the synthesis of spiro compounds. The reaction conditions considered ideal were determined from a methodological study varying solvent, catalyst, amount of catalyst, temperature, and heating mode. Finally, the generality of the methodology was evaluated by exploring the scope of the reaction, varying the starting materials (isatin, malononitrile, and barbituric acid). Overall, the twelve spi
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13

Wu, Mengyao, Yilin Wang, Xiaojun Tan, and Jinsong Gu. "Theoretical study on the reaction between phosphacyclopropenylidene and ethylene: An alternative approach to the formation of phosphorus-bearing heterocyclic compound." Journal of the Serbian Chemical Society 85, no. 9 (2020): 1175–84. http://dx.doi.org/10.2298/jsc191217026w.

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The reaction mechanism between phosphacyclopropenylidene and ethylene has been systematically investigated at the B3LYP/6-311++G(d,p) level of theory in order to better understand the reactivity of unsaturated cyclic phosphorus-bearing carbene. Geometry optimizations and vibrational analyses have been performed for the stationary points on the potential energy surface of the system. Calculations show that the spiro bicyclic intermediate could be produced through the cycloaddition process between phosphacyclopropenylidene and ethylene initially. The reaction mechanism is illustrated with the fr
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14

Wang, Yilin, Mengyao Wu, Xiaojun Tan, and Jinsong Gu. "Insights into the reaction mechanism between phosphacyclopropenylidene and methyleneimine: A theoretical study." Main Group Chemistry 19, no. 3 (2020): 237–44. http://dx.doi.org/10.3233/mgc-200906.

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The reaction mechanism between phosphacyclopropenylidene and methyleneimine has been systematically investigated at the M06–2X/6–311++G(d,p) level of theory in order to better understand the reactivity of unsaturated cyclic phosphorus-bearing carbene. Geometry optimizations and vibrational analyses have been conducted for the stationary points on the potential energy surface of the system. Calculations show that the spiro bicyclic intermediate could be produced through the cycloaddition process between phosphacyclopropenylidene and methyleneimine initially. The reaction mechanism is illustrate
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15

Shukla, Paritosh, Ashok Sharma, Leena Fageria, and Rajdeep Chowdhury. "Novel Spiro/non-Spiro Pyranopyrazoles: Eco-Friendly Synthesis, In-vitro Anticancer Activity, DNA Binding, and In-silico Docking Studies." Current Bioactive Compounds 15, no. 2 (2019): 257–67. http://dx.doi.org/10.2174/1573407213666170828165512.

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Background: Cancer being a deadly disease, many reports of new chemical entities are available. Pyranopyrazole (PPZ) compounds have also been disclosed as bioactive molecules but mainly as antimicrobial agents. Based on one previous report and our interest in anticancer drug design, we decided to explore PPZs as anticancer agents. To the best of our knowledge, we found that a comprehensive study, involving synthesis, in-vitro biological activity determination, exploration of the mechanism of inhibition and finally in-silico docking studies, was missing in earlier reports. This is what the pres
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16

Rys, Paul, Ruth Weber, and Qinglan Wu. "Light-induced change of the molecular charge in a spironaphthoxazine compound." Canadian Journal of Chemistry 71, no. 11 (1993): 1828–33. http://dx.doi.org/10.1139/v93-228.

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To evaluate the experimental conditions for the light-induced change of the molecular charge, the dependence of the photochromic reaction behaviour of the indolino spiro naphthoxazine compound 1,3,3-trimethyl-spiro[2H-indol 2,3′-[3H]naphth[2,1-b]-[1,4]oxazine] on the pH value of the solution is investigated. In the absence of UV light an acid–base equilibrium between the spiro form and a protonated closed form is established. By irradiation under appropriate acidic conditions the spiro form can be transformed into an open cationic form through the merocyanine form. Between the two open forms a
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17

Flefel, Eman M., Walaa I. El-Sofany, Reem A. K. Al-Harbi, and Mahmoud El-Shahat. "Development of a Novel Series of Anticancer and Antidiabetic: Spirothiazolidines Analogs." Molecules 24, no. 13 (2019): 2511. http://dx.doi.org/10.3390/molecules24132511.

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4-(4-Aminophenyl)-1-thia-4-azaspiro[4.5]decan-3-one 1 was prepared and allowed to react with nitrogen nucleophiles to give the corresponding hydrazones 2–4. Further, compound 1 underwent diazotization and afforded the parallel hydrazono derivative 5; moreover, compound 1 refluxed with active methylene derivatives yielded the corresponding aminospirothiazolo pyridine–carbonitrile derivative 6 and spirothiazolopyridinone–carbonitrile derivative 7. Condensation of spirothiazolidine 1 with 4-chlorobenzaldehyde gave the corresponding spiro arylidiene derivative 8, which was utilized as a component
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18

Sepsey Für, Csilla, and Hedvig Bölcskei. "New Spiro[cycloalkane-pyridazinone] Derivatives with Favorable Fsp3 Character." Chemistry 2, no. 4 (2020): 837–48. http://dx.doi.org/10.3390/chemistry2040055.

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The large originator pharmaceutical companies need more and more new compounds for their molecule banks, because high throughput screening (HTS) is still a widely used method to find new hits in the course of the lead discovery. In the design and synthesis of a new compound library, important points are in focus nowadays: Lipinski’s rule of five (RO5); the high Fsp3 character; the use of bioisosteric heterocycles instead of aromatic rings. With said aim in mind, we have synthesized a small compound library of new spiro[cycloalkane-pyridazinones] with 36 members. The compounds with this new sca
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19

Kim, Seung Hyun, Sang Hyun Sung, Soo Young Choi, Young Keun Chung, Jinwoong Kim, and Young Choong Kim. "Idesolide: A New Spiro Compound fromIdesiapolycarpa." Organic Letters 7, no. 15 (2005): 3275–77. http://dx.doi.org/10.1021/ol051105f.

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20

Tada, Masahiro, Masashi Nagai, Chieko Okumura, Yasuko Osano, and Takao Matsuzaki. "Novel Spiro-Compound, Hyperolactone fromHypericum chinenseL." Chemistry Letters 18, no. 4 (1989): 683–86. http://dx.doi.org/10.1246/cl.1989.683.

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21

Song, Fuhang, Rui Lin, Na Yang, et al. "Antibacterial Secondary Metabolites from Marine-Derived Fungus Aspergillus sp. IMCASMF180035." Antibiotics 10, no. 4 (2021): 377. http://dx.doi.org/10.3390/antibiotics10040377.

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Four new secondary metabolites, including one spiro[anthracenone-xanthene] derivative aspergiloxathene A (1), one penicillide analogue, Δ2′-1′-dehydropenicillide (2), and two new phthalide derivatives, 5-methyl-3-methoxyepicoccone (3) and 7-carboxy-4-hydroxy-6-methoxy-5-methylphthalide (4), together with four known compounds, yicathin C (5), dehydropenicillide (6), 3-methoxyepicoccone (7), 4-hydroxy-6-methoxy-5-methylphthalide (8), were identified from the marine-derived fungus Aspergillus sp. IMCASMF180035. Their structures were determined by spectroscopic data, including high-resolution elec
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22

Bernet, Bruno, Paul M. Bishop, Maurice Caron, et al. "Formal total synthesis of erythromycin A. Part II. Preparation of a 1,7-dioxaspiro[5.5]undecane derivative of erythronolide A seco acid methyl ester from erythromycin A." Canadian Journal of Chemistry 63, no. 10 (1985): 2814–18. http://dx.doi.org/10.1139/v85-469.

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23

Mohamed, Magda F., Amr Mohamed Abdelmoniem, Ahmed H. M. Elwahy, and Ismail A. Abdelhamid. "DNA Fragmentation, Cell Cycle Arrest, and Docking Study of Novel Bis Spiro-cyclic 2-oxindole of Pyrimido[4,5-b]quinoline-4,6-dione Derivatives Against Breast Carcinoma." Current Cancer Drug Targets 18, no. 4 (2018): 372–81. http://dx.doi.org/10.2174/1568009617666170630143311.

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Background: Recently, it is reported that heterocycles containing pyrimidoquinoline moiety show a broad spectrum of medicinal and pharmacological properties including anticancer, anti-microbial, anti-inflammatory activities, analgesic and antiviral. In additions, spirocyclicoxindole containing compounds represent an important class of compounds that exhibit wide range of biological properties. The asymmetric chiral spiro carbon is considered to be the main criteria of the bioactivities. Spirooxindole structures represent the main skeleton for various alkaloids and pharmaceutically important co
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24

Kotha, Sambasivarao, Mohammad Saifuddin, Rashid Ali, and Gaddamedi Sreevani. "Spiro annulation of cage polycycles via Grignard reaction and ring-closing metathesis as key steps." Beilstein Journal of Organic Chemistry 11 (August 5, 2015): 1367–72. http://dx.doi.org/10.3762/bjoc.11.147.

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A simple synthetic strategy to C 2-symmetric bis-spiro-pyrano cage compound 7 involving ring-closing metathesis is reported. The hexacyclic dione 10 was prepared from simple and readily available starting materials such as 1,4-naphthoquinone and cyclopentadiene. The synthesis of an unprecedented octacyclic cage compound through intramolecular Diels–Alder (DA) reaction as a key step is described. The structures of three new cage compounds 7, 12 and 18 were confirmed by single crystal X-ray diffraction studies.
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25

Macháček, Vladimír, Makky M. M. Hassanien, Vojeslav Štěrba, and Antonín Lyčka. "Formation of the Meisenheimer spiro adduct of N-(2,4,6-trinitrophenyl)alanine methylamide and its rearrangement to 2-amino-N-methyl-N-(2,4,6-trinitrophenyl)propanamide." Collection of Czechoslovak Chemical Communications 51, no. 9 (1986): 1972–85. http://dx.doi.org/10.1135/cccc19861972.

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N-(2,4,6-trinitrophenyl)alanine methylamide (I) undergoes base-catalyzed cyclization in methanol to give the spiro adduct II. In aniline-anilinium chloride buffers, the spiro adduct is protonated at the oxygen atom of 2-nitro group to give the neutral compound III. In 4-bromoaniline buffers or by action of methanolic hydrogen chloride, the compound III is opened to E and Z isomers of 2-amino-N-methyl-N-(2,4,6-trinitrophenyl)propanamide hydrochloride (IV). The rate-limiting step of cyclization of compound Z-IV to compound III consists in the isomerization Z-IV → E-IV. At higher pH values (aceta
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26

Sayed, Hayam, Hebat-Allah Abbas, Eman Morsi, Abd Amr, and Nayera Abdelwahad. "Antimicrobial activity of some synthesized glucopyranosyl-pyrimidine carbonitrile and fused pyrimidine systems." Acta Pharmaceutica 60, no. 4 (2010): 479–91. http://dx.doi.org/10.2478/v10007-010-0033-8.

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Antimicrobial activity of some synthesized glucopyranosyl-pyrimidine carbonitrile and fused pyrimidine systems 3-Amino-5-(4-chlorophenylamino)-4-cyanofuran-2-carboxamide (2) was used as the key molecule for preparation of various furopyrimidines 3-9 and formation of spiro-cycloalkane furopyrimidines 10, 11. Also, poly fused heterocyclic compounds 13-17 were prepared from compound 2. The synthesized compounds were screened for their antimicrobial activity.
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27

FATHI-AL-BURGUS, Abdallah, Omar THANOON-ALI, and Omar YOUNIS AL-ABBASY. "Design, synthesis and molecular docking of new spiro heterocyclic coumarin as antibacterial agents." Revue Roumaine de Chimie 69, no. 7-8 (2024): 399–404. http://dx.doi.org/10.33224/rrch.2024.69.7-8.07.

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In this study, coumarin derivatives were synthesized from coumarin 3-carbohydrazide (1) and 4-(pyrimidin-2-yl diazenyl)-antipyrine (2), leading to the intermediate compound (3). The final compounds were synthesized through the cyclocondensation of compound (3) with mercaptoacetic acid, acetic anhydride, sodium azide, 2-aminobenzoic acid, and maleic anhydride. This process resulted in the formation of five spiro heterocyclic coumarins (4a-e) respectively. The novel compounds were purified by column chromatography, and were identified by FT-IR,1H, and 13C-NMR. The antibacterial activity of the p
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28

Maihesuti, L., P. Lan, M. Imerhasan, K. A. Eshbakova, and X. Jia. "A New Spiro Compound from Caragana acanthophylla." Chemistry of Natural Compounds 53, no. 4 (2017): 646–48. http://dx.doi.org/10.1007/s10600-017-2081-5.

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29

Silva, Daiana K. Frade, Sâmia S. Duarte, Thaís M. H. Lisboa, et al. "Antitumor Effect of a Novel Spiro-Acridine Compound is Associated with Up-Regulation of Th1-Type Responses and Antiangiogenic Action." Molecules 25, no. 1 (2019): 29. http://dx.doi.org/10.3390/molecules25010029.

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Tumor cells have specific features, including angiogenesis induction, cell cycle dysregulation, and immune destruction evasion. By inducing a T helper type 2 (Th2) immune response, tumor cells may favor immune tolerance within the tumor, which allows progression of cancer growth. Drugs with potential antitumor activity are the spiro-acridines, which is a promising new class of acridine compounds. Herein, the novel spiro-acridine (E)-5′-oxo-1′-((3,4,5-trimethoxybenzylidene)amino)-1′,5′-dihydro-10H-spiro[acridine-9,2′-pyrrole]-4′-carbonitrile (AMTAC-17) was synthesized and tested for antitumor e
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30

El-Ossaily, Y. A. B., R. M. Zaki, and S. A. Metwally. "Investigation and Synthesis of Some Novel Spiro Heterocycles Related to Indoline Moiety." Journal of Scientific Research 6, no. 2 (2014): 293–307. http://dx.doi.org/10.3329/jsr.v6i2.17590.

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Reactions of indole-2,3-dione 1 with 2-mercaptobenzimidazole, o-phenylenediamine, 2-aminophenol, 2-aminobenzothiazole, 2-aminobenzimidazole and 3-methyl-1-phenyl-2-pyrazolin-5-one were carried out to give compounds spiroindolethiazetobenzimidazole 2, spirobenzimidazole(oxazole)indoline 3a,b, benzothiazol(imidazol) iminoindolinone 4a,b and methyloxoindolylidenepyrazolone 5 respectively. Compound 5 was reacted with 2-aminophenol as well as o-phenylenediamine to give new spirooxazepine and diazepine derivatives 6a,b respectively. Reaction of 5 with nitrogen nucleophiles as well as carbon nucleoph
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31

Wang, Guisheng, Yilin Yuan, Zhaokun Li, Junhao Zhu, Zhigang She, and Yan Chen. "Cytosporones with Anti-Inflammatory Activities from the Mangrove Endophytic Fungus Phomopsis sp. QYM-13." Marine Drugs 21, no. 12 (2023): 631. http://dx.doi.org/10.3390/md21120631.

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Six previously undescribed cytosporone derivatives (phomotones A-E (1–5) and phomotone F (13)), two new spiro-alkanol phombistenes A-B (14–15), and seven known analogs (6–12) were isolated from the mangrove endophytic fungus Phomopsis sp. QYM-13. The structures of these compounds were elucidated using spectroscopic data analysis, electronic circular dichroism (ECD), and 13C NMR calculations. Compound 14 features an unprecedented 1,6-dioxaspiro[4.5]decane ring system. All isolates were evaluated for their inhibitory effect on nitric oxide (NO) in LPS-induced RAW264.7 cells. The results showed t
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32

Hala Ayad Mohamed Rasheed and Suaad M. H. Al-Majidi. "Synthesis, Molecular Docking Study, Anti-Oxidant and Cytotoxicity Evaluation of New Spiro Six Membered Ring Derivatives of 5-nitro isatin." Iraqi Journal of Pharmaceutical Sciences( P-ISSN 1683 - 3597 E-ISSN 2521 - 3512) 33, no. 2 (2024): 36–48. http://dx.doi.org/10.31351/vol33iss2pp36-48.

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Spiro-5-nitro isatino six memberd ring (quinazoline-4-one, thiazine-4-one and oxazine-4-one) respectively were produced by a cycloaddition of 5-nitro isatin Schiff bases [1–5] with anthranilic acid, o-mercapto benzoic acid and salicylic acid. 1HNMR and 13CNMR nuclear magnetic resonance spectroscopies, as well as Fourier-transform infrared spectroscopy, were used to identify the structures of the obtained compounds. These spiro-5-nitro isatin are of interest to us due to their potential antioxidant and anticancer properties. The MTT assay ((3-(4,5-Dimethylthiazol-2-yl)-2,5-Diphenyltetrazolium B
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33

Tourneur, P., F. Lucas, C. Quinton, et al. "White-light electroluminescence from a layer incorporating a single fully-organic spiro compound with phosphine oxide substituents." Journal of Materials Chemistry C 8, no. 41 (2020): 14462–68. http://dx.doi.org/10.1039/d0tc03285a.

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34

Govindan, E., PanneerSelvam Yuvaraj, Boreddy Siva Rami Reddy, K. Premalatha, and A. SubbiahPandi. "(4S)-5′-Chloro-3,7,7-trimethyl-5,6,7,8-tetrahydro-4H-spiro[1,2-oxazolo[5,4-b]quinoline-4,3′-indole]-2′,5-dione." Acta Crystallographica Section E Structure Reports Online 70, no. 2 (2014): o173. http://dx.doi.org/10.1107/s1600536814000191.

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In the title compound, C20H18ClN3O3, the five- and six-membered heterocycles fused through a spiro C atom are inclined to each other at an angle of 87.4 (1)°. In the tricyclic ring system, the cyclohexene ring adopts an envelope conformation with the spiro atom as the flap. In the crystal, two sets of N—H...O hydrogen bonds link the molecules into columns containing centrosymmetricR22(7) ring motifs and propagating along theb-axis direction.
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35

Mohamed, Abou-El-Hamd H., Ali K. Khalafallah, and Afifi H. Yousof. "Biotransformation of Glabratephrin, a Rare Type of Isoprenylated Flavonoids, by Aspergillus niger." Zeitschrift für Naturforschung C 63, no. 7-8 (2008): 561–64. http://dx.doi.org/10.1515/znc-2008-7-816.

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Microbial transformation of glabratephrin, the major isolated compound from Tephrosia purpurea, afforded pseudosemiglabrin. The formation of the transformed compound seems to be performed via ring opening-closure of a five-membered ring causing transformation from a spiro into a fused system. The structure of the transformed compound was determined by comprehensive NMR studies, including DEPT, COSY, HMQC, NOE and MS.
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36

Gambuti, Francesco, Jacopo Pizzorno, Chiara Lambruschini, Renata Riva, and Lisa Moni. "Synthesis of spiroindolenines through a one-pot multistep process mediated by visible light." Beilstein Journal of Organic Chemistry 20 (October 29, 2024): 2722–31. http://dx.doi.org/10.3762/bjoc.20.230.

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Spiro-heterocyclic indolenines are privileged scaffolds widely present in numerous indole alkaloids. Here, we develop a novel approach for the one-pot multistep synthesis of different spiro[indole-isoquinolines]. The protocol proposed involves the visible light mediated oxidation of N-aryl tertiary amines using bromochloroform with the generation of a reactive iminium species, which reacts with an isocyanide and an electron-rich aniline in a three-component Ugi-type reaction to give an α-aminoamidine. This compound might undergo an additional visible light-mediated oxidation to furnish a secon
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37

Chalmers, Brian A., David B. Cordes, Aidan P. McKay, Iain L. J. Patterson, Nadiia Vladymyrova, and Iain A. Smellie. "3′H-Spiro[dibenzo[c,h]xanthene-7,1′-isobenzofuran]-3′-one." Molbank 2025, no. 3 (2025): M2033. https://doi.org/10.3390/m2033.

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Target compound 3′H-spiro[dibenzo[c,h]xanthene-7,1′-isobenzofuran]-3′-one (1) has long been known to be a by-product obtained from the preparation of naphtholphthalein. The structure of compound 1 was elucidated in the early 20th century; however, this compound has not previously been fully characterized using modern techniques. In this report, 1H NMR and 13C NMR spectra are provided. X-ray crystallography is also used to characterize the title compound for the first time.
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38

Augustine, T., V. Ramkumar, S. Arul Antony, and Charles C. Kanakam. "6′′-Methoxy-1′-methyl-4′-phenylacenaphthene-1-spiro-2′-pyrrolidine-3′-spiro-3′′-chroman-2,4′′-dione." Acta Crystallographica Section E Structure Reports Online 63, no. 11 (2007): o4412. http://dx.doi.org/10.1107/s1600536807051264.

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39

Schaefer, W. P., and J. Abulū. "An Indanyl Precursor to a Chiral Spiro Compound." Acta Crystallographica Section C Crystal Structure Communications 51, no. 11 (1995): 2364–66. http://dx.doi.org/10.1107/s0108270195005609.

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40

Schaefer, W. P., L. M. Henling, H. C. McBay, and J. Abulū. "A Pinacol Precursor to a Chiral Spiro Compound." Acta Crystallographica Section C Crystal Structure Communications 52, no. 1 (1996): 104–7. http://dx.doi.org/10.1107/s0108270195010213.

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41

Kuznetsova, Juliana V., Varvara T. Tkachenko, Lada M. Petrovskaya, et al. "[3+2]-Cycloaddition of Nitrile Imines to Parabanic Acid Derivatives—An Approach to Novel Spiroimidazolidinediones." International Journal of Molecular Sciences 25, no. 1 (2023): 18. http://dx.doi.org/10.3390/ijms25010018.

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Approximately 1,3-Dipolar cycloaddition of imidazolidine derivatives containing exocyclic double bonds is a convenient method of creating spiro-conjugated molecules with promising anticancer activity. In this work, the derivatives of parabanic acid (2-thioxoimidazolidine-4,5-diones and 5-aryliminoimidazolidine-2,4-diones) were first investigated as dipolarophiles in the reactions with nitrile imines. The generation of nitrile imines was carried out either by the addition of tertiary amine to hydrazonoyl chlorides «drop by drop» or using the recently proposed diffusion mixing technique, which l
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42

Guan, Zong, Jan C. Namyslo, Martin H. H. Drafz, Martin Nieger, and Andreas Schmidt. "Dimerisation, rhodium complex formation and rearrangements of N-heterocyclic carbenes of indazoles." Beilstein Journal of Organic Chemistry 10 (April 10, 2014): 832–40. http://dx.doi.org/10.3762/bjoc.10.79.

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Deprotonation of indazolium salts at low temperatures gives N-heterocyclic carbenes of indazoles (indazol-3-ylidenes) which can be trapped as rhodium complexes (X-ray analysis). In the absence of Rh, the indazol-3-ylidenes spontaneously dimerize under ring cleavage of one of the N,N-bonds and ring closure to an indazole–indole spiro compound which possesses an exocyclic imine group. The E/Z isomers of the imines can be separated by column chromatography when methanol is used as eluent. We present results of a single crystal X-ray analysis of one of the E-isomers, which equilibrate in solution
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43

Marinov, M., D. Stoitsov, M. M. Frenkeva, P. Marinova, P. Penchev, and N. Stoyanov. "A complete 1H and 13C NMR data assignment for two substituted fluorenylspirohydantoins." Bulgarian Chemical Communications 56, no. D1 (2024): 67–72. http://dx.doi.org/10.34049/bcc.56.d.s1p28.

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This work presents the spectral characterization of 1',3'-bis(hydroxymethyl)-2'H,5'H-spiro[fluorene-9,4'- imidazolidine]-2',5'-dione and 2-bromo-2'H,5'H-spiro[fluorene-9,4'-imidazolidine]-2',5'-dione. The structures of the substituted fluorenylspirohydantoins were verified by 1H NMR and 13C NMR spectroscopy. In addition, 2D NMR spectra, including 1H1H COSY, HMQC, HMBC and 1H1H NOESY sequences, were used for a complete assignment of the 1Hand 13C chemical shifts for each compound.
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44

Hu, Bin-Yuan, Da-Peng Qin, Shao-Xiang Wang, Jing-Jing Qi, and Yong-Xian Cheng. "Novel Terpenoids with Potent Cytotoxic Activities from Resina Commiphora." Molecules 23, no. 12 (2018): 3239. http://dx.doi.org/10.3390/molecules23123239.

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A novel sesquiterpene dimer, spirocommiphorfuran A (1); two new cadinane sesquiterpenoids, commiphorenes A (2) and B (3); along with three known terpenoids (4–6), were isolated from Resina Commiphora. The structures of these new compounds were characterized by NMR, HRESIMS, quantum chemical computation, and X-ray diffraction analysis. Compound 1 features a 7-oxabicyclo[2.2.1]heptane-2-ene core, representing the first example of germacrane-type sesquiterpene dimer fused via a spiro ring system. Compound 2 is a novel sesquiterpene with a completely new carbon skeleton, which is characteristic of
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45

Kshatriya, Monika R., and Jinal A. Gajja. "Synthesis, characterization, and biological profiling of novel benzotriazole-thio linked derivatives as promising anti-inflammatory, analgesic, and antibacterial agents." Current Chemistry Letters 14, no. 1 (2025): 41–50. http://dx.doi.org/10.5267/j.ccl.2024.10.003.

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A series of new compounds, Substituted 2-((2H-benzo[d][1,2,3]triazol-2-yl)thio)-N'-(2-oxoindolin-3-ylidene)acetohydrazide (3a-3g), 2-((2H-benzo[d][1,2,3]triazol-2-yl)thio)-N-(2,4'-dioxospiro[indoline-3,2'-thiazolidin]-3'yl)acetamide (4a-4g), and 2'-(((2H-benzo[d][1,2,3]triazol-2-yl)thio)methyl)spiro[indoline-3,5'-thiazolo[4,3-b][1,3,4]oxadiazol]-2-one (5a-5g), were synthesized and checked for their anti-inflammatory, analgesic, and antibacterial activities. Compound 5d proved to be the most potent anti-inflammatory and antibacterial agent. The analgesic activity, however, was maximum in compou
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46

Bando, Masayoshi, Yuki Mizukami, Kiyohiko Nakajima, Zhiyi Song, and Tamotsu Takahashi. "Formation of a spiro compound via coupling of a cyclopentadienyl ligand with a diene moiety of titanacyclopentadiene." Dalton Transactions 46, no. 47 (2017): 16408–11. http://dx.doi.org/10.1039/c7dt03789a.

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47

Tong, Junjie, Yang Zhang, Yang Xu, et al. "Spirocitrinols A and B, citrinin derivatives with a spiro[chromane-2,3′-isochromane] skeleton from Penicillium citrinum." RSC Advances 13, no. 9 (2023): 6124–29. http://dx.doi.org/10.1039/d3ra00665d.

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Two new citrinin-derived metabolites spirocitrinols A (1) and B (2) with a spiro[chromane-2,3′-isochromane] skeleton were isolated from cultures of Penicillium citrinum. Compound 1 showed moderate cytotoxicity towards human tumor cells.
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48

Sharma, Sakshi, Goutam Brahmachari, Rajni Kant, and Vivek K. Gupta. "One-pot green synthesis of biologically relevant novel spiro[indolin-2-one-3,4′-pyrano[2,3-c]pyrazoles] and studies on their spectral and X-ray crystallographic behaviors." Acta Crystallographica Section B Structural Science, Crystal Engineering and Materials 72, no. 3 (2016): 335–43. http://dx.doi.org/10.1107/s2052520616005060.

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Synthesesviagreen route and single-crystal X-ray structural investigations have been carried out for three spiro[indolin-2-one-3,4′-pyrano[2,3-c]pyrazole] derivatives, 6′-amino-2-oxo-3′-propyl-2′H-spiro[indoline-3,4′-pyrano[2,3-c]pyrazole]-5′-carbonitrile dimethyl sulfoxide monosolvate (5a), 6′-amino-5-fluoro-2-oxo-3′-propyl-2′H-spiro[indoline-3,4′-pyrano[2,3-c]pyrazole]-5′-carbonitrile dimethyl sulfoxide monosolvate (5b) and methyl 6′-amino-5-cyano-1-methyl-2-oxo-3′-propyl-2′H-spiro[indoline-3,4′-pyrano[2,3-c]pyrazole]-3′-carboxylate 0.25 hydrate (5c), respectively. Compounds (5a) and (5b) cr
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49

Rether, Jan, Gerhard Erkel, Timm Anke та Olov Sterner. "Inhibition of inducible TNF-α expression by oxaspirodion, a novel spiro-compound from the ascomycete Chaetomium subspirale". Biological Chemistry 385, № 9 (2004): 829–34. http://dx.doi.org/10.1515/bc.2004.108.

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Abstract In a search for compounds inhibiting the inducible TNF-αa promoter activity in T cells, a new spiro-compound, designated oxaspirodion, was isolated from fermentations of the ascomycete Chaetomium subspirale. Oxaspirodion inhibited TNF-α promoter-driven luciferase reporter gene expression with an IC50 value of 2.5 µg/ml (10 µM) in TPA/ionomycin-stimulated Jurkat T cells. Studies on the mode of action of the compound revealed that the inhibition of the TNF-α promoter activity is caused by an inhibition of the phosphorylation of the ERK1/2 kinases. In addition, oxaspirodion inhibited the
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50

Pan, Bowen, Tao Wang, Liangliang Zheng, et al. "Synthesis of Novel Benzofuran Spiro-2-Pyrrolidine Derivatives via [3+2] Azomethine Ylide Cycloadditions and Their Antitumor Activity." International Journal of Molecular Sciences 25, no. 24 (2024): 13580. https://doi.org/10.3390/ijms252413580.

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A synthetic strategy of a three-component spiro-pyrrolidine compound based on benzofuran via an [3+2] azomethine ylide cycloaddition reaction is reported herein. Under mild optimal conditions, this reaction can quickly produce potentially bioactive compounds with a wide range of substrates, high yield, and simple operation. The desired products were obtained with a yield of 74–99% and a diastereomeric ratio (dr) of &gt;20:1. Subsequently, the inhibitory effects of the compounds on the cell viability of the human cancer cell line HeLa and mouse cancer cell line CT26 were evaluated. Compounds 4b
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