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Journal articles on the topic 'Imidazo[2,1-b][1,3,4]thiadiazole derivative'

Author: Grafiati

Published: 9 March 2023

Last updated: 10 March 2023

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1

Singh, Satvir, Divya Bhandari, Monika Gupta, Chamanpreet Kaur, Anju Rani, and Sunita Devi. "SYNTHESIS, SPECTRAL STUDIES AND BIOLOGICAL ACTIVITY OF SOME IMIDAZO [2, 1-B] [1, 3, 4] THIADIAZOLE DERIVATIVES." Indian Drugs 59, no. 01 (2022): 23–27. http://dx.doi.org/10.53879/id.59.01.12612.

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Benzoic acid substituted imidazo[2,1-b][1,3,4]thiadiazoles were synthesized using appropriate reaction scheme. The synthesized derivatives were then purified and elucidated for their structure by measuring their melting points, infra-red spectra and proton NMR spectra. The progress of the reaction was determined by using thin layer chromatography technique. The antimicrobial potential of the synthesized derivatives was evaluated against S. aureus and E. coli. The zone of inhibition (mm) was measured. Reported derivatives showed good to moderate antibacterial activity

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2

Abu-Hashem, Ameen Ali, and Sami A. Al-Hussain. "Design, Synthesis of New 1,2,4-Triazole/1,3,4-Thiadiazole with Spiroindoline, Imidazo[4,5-b]quinoxaline and Thieno[2,3-d]pyrimidine from Isatin Derivatives as Anticancer Agents." Molecules 27, no. 3 (2022): 835. http://dx.doi.org/10.3390/molecules27030835.

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The current work aims to design and synthesis a new series of isatin derivatives and greatly enhances their cytotoxic activity. The derivatives 3-((bromophenyl) imino)-1-(morpholino (pyridine) methyl) indolin-2-one, 2-((oxoindoline) amino) benzoic acid, 3-(thiazolo-imino) indolinone, ethyl-2-((oxoindolin-3-ylidene)amino)-benzothiophene-3-carboxylate, 1-(oxoindoline)-benzo[4,5] thieno [2,3-d]pyrimidin-4(1H)-one, ethyl-2-(2-oxoindoline) hydrazine-1-carboxylate, N-(mercapto-oxo-pyrimidine)-2-(oxoindoline) hydrazine-1-carboxamide, N-(oxo-thiazolo[3,2-a] pyrimidine)-2-(oxoindolin-ylidene) hydrazine

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3

Rajeswar Rao, V., M. S. Rao, and T. V. Padmanabha Rao. "A novel synthesis of thiazolyl, imidazothiadiazolyl, and thiadiazinyl-2H-1-benzopyran-2-ones." Collection of Czechoslovak Chemical Communications 51, no. 10 (1986): 2214–21. http://dx.doi.org/10.1135/cccc19862214.

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3-Acetylcoumarins I with arylthiourea in the presence of iodine gave substituted 3-(2-arylamino-4-thiazolyl)-2H-1-benzopyran-2-ones (IIa-IIc). The structures of these products have been confirmed and they were converted into acetyl derivatives (IId-IIf). Condensation of various 3-(2-bromoacetyl)-2H-1-benzopyran-2-ones (III) with 2-amino-6-substituted thiadiazoles IV in the presence of ethanol and dimethylformamide yielded substituted 3-(2-substituted imidazo[2,1-b]thiadiazol-6-yl)-2H-1-benzopyran-2-ones (VI). Reaction of III with 3-substituted 4-amino-5-mercapto-S-triazole VII resulted in the

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4

Haggam, Reda Ahmed, Mohamed Gomma Assy, Mohamed Hassan Sherif, and Mohamed Mohamed Galahom. "A series of 1,3-imidazoles and triazole-3-thiones based thiophene-2-carboxamides as anticancer agents: Synthesis and anticancer activity." European Journal of Chemistry 9, no. 2 (2018): 99–106. http://dx.doi.org/10.5155/eurjchem.9.2.99-106.1701.

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By addition of semicarbazide or phenylhydrazine hydrochloride to thienoylisothiocyanate (1) resulted in building of thiosemicarbazide derivative (2), triazole derivative (4) and thiophene-2-carboxamide (5), respectively. Basic cyclization of compound 2 led to formation of oxadiazine (3). Synthesis of thiadiazine derivative (6) was achieved via reaction of compound 5 and maleic anhydride in triethyl amine. Heating of compound 5 with ethyl chloroacetate or sodium ethoxide produced thiadiazine derivative (7) and triazolethione (8), respectively. Thiosemicarbazide derivative 11 was synthesized by

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5

Sowmya, A., G. N. Anil Kumar, Sujeet Kumar, and Subhas S. Karki. "The crystal structure of 6-(4-chlorophenyl)-2-(4-methylbenzyl)imidazo[2,1-b][1,3,4]thiadiazole-5-carbaldehyde." Acta Crystallographica Section E Crystallographic Communications 72, no. 10 (2016): 1460–62. http://dx.doi.org/10.1107/s2056989016014754.

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In the title imidazo[2,1-b][1,3,4]thiadiazole derivative, C19H14ClN3OS, the 4-methylbenzyl and chlorophenyl rings are inclined to the planar imidazo[2,1-b][1,3,4]thiadiazole moiety (r.m.s. deviation = 0.012 Å) by 64.5 (1) and 3.7 (1)°, respectively. The molecular structure is primarily stabilized by a strong intramolecular C—H...O hydrogen bond, leading to the formation of a pseudo-seven-memberedS(7) ring motif, and a short intramolecular C—H...N contact forming anS(5) ring motif. In the crystal, molecules are linked by pairs of C—H...S hydrogen bonds, forming inversion dimers. The dimers are

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6

Ibrahim, Yusria R. "Synthesis of imidazo- and pyrazolothiadiazoles from dithiobiureas and dimethyl ethynedicarboxylate." Journal of Chemical Research 2009, no. 10 (2009): 602–6. http://dx.doi.org/10.3184/030823409x12510192920270.

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Microwave irradiation of 1-substituted-2, 5-dithiobiureas and 1, 6-disubstituted-2, 5-dithiobiureas with dimethyl ethynedicarboxylate gave methyl 2-{6-oxo-2-(substituted amino)imidazo-[2, 1- b][1, 3, 5]thiadiazol-5(6 H)-ylidene} acetate and methyl 7-oxo-1, 3-bis(substituted imino)-3, 7-dihydro-1 H-pyrazolo[1, 2- c][1, 3, 4]thiadiazole-5-carboxylate. Rationales for these transformations are presented.

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7

Gad-Elkareem, Mohamed A. M., Azza M. Abdel-Fattah, and Mohamed A. A. Elneairy. "Pyrazolo[3,4-b]pyridine in heterocyclic synthesis: synthesis of new pyrazolo[3,4-b]pyridines, imidazo[1',2':1,5]pyrazolo[3,4-b]pyridines, and pyrido[2',3':3,4]pyrazolo[1,5-a]pyrimidines." Canadian Journal of Chemistry 85, no. 9 (2007): 592–99. http://dx.doi.org/10.1139/v07-089.

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Pyrazolo[3,4-b]pyridine derivatives 7 and 9 were synthesized via the reaction of 3-amino-1H-pyrazolo-[3,4-b]pyridine derivative 2 with ω-bromoacetophenones. Reaction of 7 and 9 with Ac2O afforded the imidazo[1',2':1,5]py razolo[3,4-b]pyridine derivative 8 and pyrazolo[3,4-b]pyridine derivative 10, respectively. Reaction of 2 with chloroacetonitrile followed by DMF-DMA gave imidazo[1',2':1,5]pyrazolo[3,4-b]pyridines 4 and 5, respectively. Acetyl acetone and 1,1-dicyano-2,2-dimethylthioethene were reacted with 2 to afford the pyrido[2',3':3,4]pyrazolo-[1,5-a]-pyrimidines 11 and 14, respectively.

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8

Praveen, Aletti S., Hemmige S. Yathirajan, Manpreet Kaur, et al. "Different patterns of supramolecular assembly in constitutionally similar 6-arylimidazo[2,1-b][1,3,4]thiadiazoles." Acta Crystallographica Section C Structural Chemistry 70, no. 9 (2014): 920–26. http://dx.doi.org/10.1107/s2053229614018762.

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Four imidazo[2,1-b][1,3,4]thiadiazoles containing a simply-substituted 6-aryl group have been synthesized by reaction of 2-amino-1,3,4-thiadiazoles with bromoacetylarenes using microwave irradiation and brief reaction times. 6-(2-Chlorophenyl)imidazo[2,1-b][1,3,4]thiadiazole, C10H6ClN3S, (I), 6-(2-chlorophenyl)-2-methylimidazo[2,1-b][1,3,4]thiadiazole, C11H8ClN3S, (II), 6-(3,4-dichlorophenyl)imidazo[2,1-b][1,3,4]thiadiazole, C10H5Cl2N3S, (III), and 6-(4-fluoro-3-methoxyphenyl)-2-methylimidazo[2,1-b][1,3,4]thiadiazole, C12H10FN3OS, (IV), crystallize withZ′ values of 2, 1, 1 and 2 respectively.

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9

Dubey, Sonal, and Pradnya A. Bhosle. "Quantitative Structure Activity Relationship of 2, 5, 6–Trisubstituted imidazo (2, 1-b)-1, 3, 4–Thiadiazole as Anticancer Compunds." Indian Journal of Pharmaceutical Education and Research 50, no. 1 (2016): 198–204. http://dx.doi.org/10.5530/ijper.50.1.24.

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10

Hassaneen, Huwaida M. E., and Richard M. Pagni. "Synthesis of New 3-Substituted Indole Derivatives." Zeitschrift für Naturforschung B 65, no. 12 (2010): 1491–97. http://dx.doi.org/10.1515/znb-2010-1213.

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Treatment of 3-cyanoacetyl-2-methylindole (1) with phenyl isothiocyanate gave the corresponding thioacetanilide derivative 3. The thioacetanilide 3 was utilized as the key intermediate for the synthesis of some new 1,3,4-thiadiazole (6a, b and 9a - e), thiophene (11a, b), thiazolidin-4-one (4), thiazole (12 and 13), and benzothiazole (15) derivatives. The structures of the new compounds were elucidated on the basis of elemental analyses and spectral data.

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11

Singh, Yashveer, Baljeet Kaur, Amandeep Kaur, Vivek Kumar Gupta, and Monika Gupta. "Synthesis, spectral studies and biological activity of 2, 3-disubstituted imidazo [2, 1-b] benzothiazole derivatives." Indian Journal of Pharmaceutical and Biological Research 6, no. 01 (2018): 01–08. http://dx.doi.org/10.30750/ijpbr.6.1.1.

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Benzothiazole is a heterocyclic compound formed by the fusion of benzene and thiazole ring. The moiety had been reported to act via competing with ATP binding site at the catalytic domain of tyrosine kinase. The present work involves the synthesis and biological evaluation of 4, 5 disubstituted imidazo [2, 1-b] benzothiazole derivatives. The antimicrobial activity of the synthesized derivatives was carried out against Gram + ve bacteria Staphylococcus aureus (MTCC 3160) and Gram –ve bacteria Bordetella bronchiseptica (MTCC 6838), Pseudomonas aeruginosa (T11) and fungal strains Candida albicans

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12

Štefan, Leo, Ana Čikoš, Robert Vianello, Ivica Đilović, Dubravka Matković-Čalogović, and Miljenko Dumić. "Chemistry of Spontaneous Alkylation of Methimazole with 1,2-Dichloroethane." Molecules 26, no. 22 (2021): 7032. http://dx.doi.org/10.3390/molecules26227032.

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Spontaneous S-alkylation of methimazole (1) with 1,2-dichloroethane (DCE) into 1,2-bis[(1-methyl-1H-imidazole-2-yl)thio]ethane (2), that we have described recently, opened the question about its formation pathway(s). Results of the synthetic, NMR spectroscopic, crystallographic and computational studies suggest that, under given conditions, 2 is obtained by direct attack of 1 on the chloroethyl derivative 2-[(chloroethyl)thio]-1-methyl-1H-imidazole (3), rather than through the isolated stable thiiranium ion isomer, i.e., 7-methyl-2H, 3H, 7H-imidazo[2,1-b]thiazol-4-ium chloride (4a, orthorhombi

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13

Wang, Xiu-Yan, Yu He, and Fei-Fei Liu. "Two New Cd(II) and Co(II) Coordination Polymers Based on a 1,10- Phenanthroline Derivative and Tri- or Tetra-Carboxylates: Syntheses, Structures and Photoluminesce." Zeitschrift für Naturforschung B 67, no. 5 (2012): 459–64. http://dx.doi.org/10.5560/znb.2012-0029.

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Two new coordination polymers constructed with the 1,10-phenanthroline derivative 2-(2-chloro- 6-fluorophenyl)-1H-imidazo[4,5-f][1,10]-phenanthroline (L) and different carboxylates, namely, [Cd2(L)2(1,3,5-BTC)(Cl)]·H2O (1) and [Co2(L)2(1,2,4,5-BTC)(H2O)2] (2), have been synthesized under hydrothermal conditions (1,3,5-BTC = 1,3,5-benzenetricarboxylate anion and 1,2,4,5-BTC = 1,2,4,5-benzenetetracarboxylate anion). Crystal data for 1: C47H25Cd2Cl3F2N8O7, triclinic, space group P¯1, a = 10:1084(5), b = 14:9285(7), c = 15:2930(4)Å , α = 72:1050(10), β = 86:160(2), γ = 79:6000(10)°, V = 2159:88(16

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14

A. Khalil, Mohamed, Samia M. Sayed, and Mohamed A. Raslan. "Reactivity of 2-Cyano-N-(4-(1-Methyl-1H-benzo[d]imidazol-2-yl)-3-(Methylthio)-1-Phenyl-1H-Pyrazol-5-yl)Acetamide: A Facile Synthesis of Pyrazole, Thiazole, 1,3,4-Thiadiazole and Polysubstituted Thiophene Derivatives." American Journal of Organic Chemistry 2, no. 6 (2012): 161–70. http://dx.doi.org/10.5923/j.ajoc.20120206.06.

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15

Dróżdż, Agnieszka, Adrianna Sławińska-Brych, Dominika Kubera, et al. "Effect of Antibiotic Amphotericin B Combinations with Selected 1,3,4-Thiadiazole Derivatives on RPTECs in an In Vitro Model." International Journal of Molecular Sciences 23, no. 23 (2022): 15260. http://dx.doi.org/10.3390/ijms232315260.

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4-(5-methyl-1,3,4-thiadiazole-2-yl) benzene-1,3-diol (C1) and 4-[5-(naphthalen-1-ylmethyl)-1,3,4-thiadiazol-2-yl] benzene1,3-diol (NTBD) are representative derivatives of the thiadiazole group, with a high antimycotic potential and minimal toxicity against normal human fibroblast cells. The present study has proved its ability to synergize with the antifungal activity of AmB. The aim of this work was to evaluate the cytotoxic effects of C1 or NTBD, alone or in combination with AmB, on human renal proximal tubule epithelial cells (RPTECs) in vitro. Cell viability was assessed with the MTT assay

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16

Wang, Xiu-Yan, Jia Guo, Hui-Lian Wang, and Qing-Wei Wang. "Synthesis and Crystal Structure of a New Pb(II) Coordination Polymer Constructed by a 1,10-Phenanthroline Derivative and a Flexible Dicarboxylate." Zeitschrift für Naturforschung B 66, no. 6 (2011): 647–50. http://dx.doi.org/10.1515/znb-2011-0614.

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The new coordination polymer, [Pb(L)(trans-1,4-chdc)] 1 (L = 1-(1H-imidazo[4,5-f][1,10]phenanthrolin-2-yl)- naphthalen-2-ol and trans-1,4-H2chdc = trans-1,4-cyclohexanedicarboxylic acid), has been hydrothermally synthesized and characterized by elemental analysis, IR spectroscopy and single-crystal X-ray diffraction. Crystal data: C31H24N4O5Pb, monoclinic, space group P21/c, a = 13.579(2), b = 9.7831(15), c = 19.958(3) Å, β = 105.058(2)°, V = 2560.3(7) Å3, Z = 4. The Pb(II) atoms are bridged by the flexible trans-1,4-chdc ligands to form a zigzag chain. The ligands L are located on both sides

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17

Rashdan, Huda R. M., Mohamad T. Abdelrahman, Ihsan A. Shehadi, Sara S. El-Tanany, and Bahaa A. Hemdan. "Novel Thiadiazole-Based Molecules as Promising Inhibitors of Black Fungi and Pathogenic Bacteria: In Vitro Antimicrobial Evaluation and Molecular Docking Studies." Molecules 27, no. 11 (2022): 3613. http://dx.doi.org/10.3390/molecules27113613.

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Novel 1,3,4-thiadiazole derivatives were synthesized through the reaction of methyl 2-(4-hydroxy-3-methoxybenzylidene) hydrazine-1-carbodithioate and the appropriate hydrazonoyl halides in the presence of a few drops of diisopropylethylamine. The chemical structure of the newly fabricated compounds was inferred from their microanalytical and spectral data. With the increase in microbial diseases, fungi remain a devastating threat to human health because of the resistance of microorganisms to antifungal drugs. COVID-19-associated pulmonary aspergillosis (CAPA) and COVID-19-associated mucormycos

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18

Shyu, Ren-Shi, Themmila Khamrang, Joen-Rong Sheu, et al. "Ir-6: A Novel Iridium (III) Organometallic Derivative for Inhibition of Human Platelet Activation." Bioinorganic Chemistry and Applications 2018 (2018): 1–14. http://dx.doi.org/10.1155/2018/8291393.

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Platelet activation has been reported to play a major role in arterial thrombosis, cancer metastasis, and progression. Recently, we developed a novel Ir(III)-based compound, [Ir(Cp∗)1-(2-pyridyl)-3-(4-dimethylaminophenyl)imidazo[1,5-a]pyridine Cl]BF4or Ir-6 and assessed its effectiveness as an antiplatelet drug. Ir-6 exhibited higher potency against human platelet aggregation stimulated by collagen. Ir-6 also inhibited ATP-release, intracellular Ca2+mobilization, P-selectin expression, and the phosphorylation of phospholipase Cγ2 (PLCγ2), protein kinase C (PKC), v-Akt murine thymoma viral onco

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19

Shehata, Medhat, Susanne Schnabl, Dita Demirtas, et al. "Effective Targeting of the PI3-K Pathway in CLL with NVP-BEZ235, a Novel Orally Available Dual PI3K/mTOR Inhibitor." Blood 112, no. 11 (2008): 3166. http://dx.doi.org/10.1182/blood.v112.11.3166.3166.

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Abstract There is growing evidence that the anti-apoptotic PI3-K/Akt pathway is involved in pathogenesis and progression of different types of cancer. We have evidence that PI3-K inhibitors such as LY294002 and wortmannin selectively induce apoptosis in CLL cells (Shehata et al Ab. Blood 2006). Recently, a new orally available PI3-K inhibitor, NVP-BEZ235 has been developed. This competitive ATP binding imidazo-quinoline derivative is already in phase I trials against solid tumors. Here we show, for the first time, the effects of NVP-BEZ235 on the viability of CLL cells in vitro. Primary CLL ce

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20

Hjouji, Mohammed Yassin, Joel T. Mague, Youssef Kandri Rodi, Younes Ouzidan, and El Mokhtar Essassi. "Ethyl 2-(6-bromo-2-phenyl-3H-imidazo[4,5-b]pyridin-3-yl)acetate." IUCrData 1, no. 12 (2016). http://dx.doi.org/10.1107/s2414314616019994.

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The title imidazo [4,5-b] pyridine derivative, C16H14BrN3O2, crystallizes with two independent molecules (1 and 2) in the asymmetric unit. In molecule 1, the pendant phenyl ring is inclined to the imidazo[4,5-b]pyridine core by 43.10 (4)° while in molecule 2 the corresponding angle is 49.43 (4)°. The two molecules differ primarily in the conformations of the ester substituents. In the crystal, molecules are linkedviaC—H...N and C—H...O hydrogen bonds, forming sheets parallel to theabplane.

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