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Journal articles on the topic 'Cyclopropyl moiety'

Author: Grafiati

Published: 4 June 2025

Last updated: 1 August 2025

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1

Časar, Zdenko. "Synthetic Approaches to Contemporary Drugs that Contain the Cyclopropyl Moiety." Synthesis 52, no. 09 (2020): 1315–45. http://dx.doi.org/10.1055/s-0039-1690058.

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The U.S. Food and Drug Administration approved 18 new drugs that incorporate the cyclopropyl structural motif in the time frame from 2012 to 2018. This review provides an overview of synthetic approaches to these drugs with emphasis on the construction of the cyclopropyl moiety or its incorporation into the key building blocks for assembly of the highlighted drugs. Based on the structural diversity of these drugs, synthetic approaches for the construction and introduction of the cyclopropyl moiety into their structure are diverse and include: cycloalkylation (double alkylation) of CH-acids, ca

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2

Al-Trawneh, Salah A., Amer H. Tarawneh, Anastassiya V. Gadetskaya, et al. "Synthesis and Cytotoxicity of Thieno[2,3-b]Pyridine Derivatives Toward Sensitive and Multidrug-Resistant Leukemia Cells." Acta Chimica Slovenica 68, no. 2 (2021): 458–65. http://dx.doi.org/10.17344/acsi.2020.6609.

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A new series of substituted ethyl 7-cyclopropyl-2-(2-aryloxo)-3-nitro-4-oxo-4,7-dihydrothieno[2,3-b]pyridine-5-carboxylates 3a–e were prepared by utilizing ethyl 2-chloro-7-cyclopropyl-3-nitro-4-oxo-4,7-dihydrothieno[2,3-b]pyridine-5-carboxylate (1) and replacing of the 2-chlorine with anions obtained from phenol (2a), salicylaldehyde derivatives 2b–d or thiophenol (2e), leading to the respective ethyl 7-cyclopropyl-2-(2-aryloxo)-3-nitro-4-oxo-4,7-dihydrothieno[2,3-b]pyridine-5-carboxylates 3a–e. The new compounds were evaluated for their in vitro cytotoxicity towards sensitive CCRF-CEM and mu

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3

Gorlov, Evgenii S., Diana V. Shuingalieva, Alexey I. Ilovaisky, Vera A. Vil’, and Alexander O. Terent’ev. "1-(((6-(Methoxycarbonyl)-5-oxononan-4-yl)oxy)carbonyl)cyclopropane-1-carboxylic Acid." Molbank 2023, no. 2 (2023): M1651. http://dx.doi.org/10.3390/m1651.

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Here, we first report the 2′-acyloxy-1,3-dicarbonyl compound construction in a three-component oxidative reaction of alkyl ketene dimer with cyclic diacyl peroxide and trimethyl orthoformate. The discovered synthesis allows us to form 2′-functionalized 1,3-dicarbonyl compounds instead of the common 2-functionalized moiety. The reaction between 4-butylidene-3-propyloxetan-2-one and cyclopropyl malonoyl peroxide proceeds in the presence of trifluoroacetic acid and trimethyl orthoformate at 120 °C for 1 h. The synthesized compound was characterized by NMR spectroscopy, mass spectrometry, and IR s

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4

Burmudžija, Adrijana, Jovana M. Muškinja, Marijana M. Kosanic, et al. "Cytotoxic Antimicrobial Activity of Dehydrozingerone based Cyclopropyl Derivatives." Chem Biodivers 2017, Epub (2017): Jul 1. https://doi.org/10.1002/cbdv.201700077.

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A small series of 1‐acetyl‐2‐(4‐alkoxy‐3‐methoxyphenyl)cyclopropanes was prepared, starting from dehydrozingerone (4‐(4‐hydroxy‐3‐methoxyphenyl)‐3‐buten‐2‐one) and its O‐alkyl derivatives. Their microbiological activities toward some strains of bacteria and fungi were tested, as well as their in vitro cytotoxic activity against some cancer cell lines (HeLa, LS174 and A549). All synthesized compounds showed significant antimicrobial activity and expressed cytotoxic activity against tested carcinoma cell lines, but they showed no significant influence on normal cell line (MRC5). Butyl derivative

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5

Alipour, Eskandar, Negar Mohammad Hosseini, Fatemeh Panah, et al. "Synthesis andIn VitroCytotoxic Activity ofN-2-(2-Furyl)-2-(chlorobenzyloxyimino)Ethyl Ciprofloxacin Derivatives." E-Journal of Chemistry 8, no. 3 (2011): 1226–31. http://dx.doi.org/10.1155/2011/842982.

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Quinolone are a class of potent broad-spectrum antibacterial drugs that target the bacterial type II DNA topoisomerases (DNA gyrase) and topoisomerase IV. In the present study, the synthesis and evaluation of cytotoxicity activity of a new series ofN-pipearzinyl quinolones containingN-2-(furyl-2-yl)-2-(chlorobenzyloxyimino) ethyl moiety(6a-c)have been studied. Preliminary screening showed that one of the new compounds, namely 7-(4-(2-(3-chlorobenzyloxyimino)-2-(furan-2-yl) ethyl) piperazin-1-yl)-1-cyclopropyl-6-fluoro-4-oxo-1, 4-dihydroquinoline-3-carboxylic acid(6b)showed significant cytotoxi

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6

Bechi, Beatrice, David Amantini, Cristina Tintori, Maurizio Botta, and Romano di Fabio. "Stereocontrolled synthesis of 5-azaspiro[2.3]hexane derivatives as conformationally “frozen” analogues of L-glutamic acid." Beilstein Journal of Organic Chemistry 10 (May 14, 2014): 1114–20. http://dx.doi.org/10.3762/bjoc.10.110.

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Several strategies aimed to “freeze” natural amino acids into more constrained analogues have been developed with the aim of enhancing in vitro potency/selectivity and, more in general, drugability properties. The case of L-glutamic acid (L-Glu, 1) is of particular importance since it is the primary excitatory neurotransmitter in the mammalian central nervous system (CNS) and plays a critical role in a wide range of disorders like schizophrenia, depression, neurodegenerative diseases such as Parkinson’s and Alzheimer’s and in the identification of new potent and selective ligands of ionotropic

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7

Li, Penghui, Qingyang Xie, Fuxian Wan, Yuanhong Zhang, and Lin Jiang. "Synthesis and Fungicidal Activity of Novel Substituted Pyrimidine-5-carboxamides Bearing Cyclopropyl Moiety." Chinese Journal of Organic Chemistry 44, no. 2 (2024): 650. http://dx.doi.org/10.6023/cjoc202307029.

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8

Kratzel, M. "Synthesis of aC-nor-morphin-6-ene by radicalic isomerization of a cyclopropyl moiety." Monatshefte f�r Chemie - Chemical Monthly 125, no. 6-7 (1994): 791–93. http://dx.doi.org/10.1007/bf01277641.

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9

Craig, Alexander J., та Bill C. Hawkins. "The Bonding and Reactivity of α-Carbonyl Cyclopropanes". Synthesis 52, № 01 (2019): 27–39. http://dx.doi.org/10.1055/s-0039-1690695.

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The cyclopropane functionality has been exploited in a myriad of settings that range from total synthesis and methodological chemistry, to medical and materials science. While it has been seen in such a breadth of settings, the typical view of the cyclopropane moiety is that its reactivity is derived primarily from the release of ring strain. While this simplified view is a useful shorthand, it ignores the specific nature of cyclopropyl molecular orbitals. This review aims to present the different facets of cyclopropane bonding by examining the main models that have been used to explain the re

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10

Boztas, Murat, Parham Taslimi, Mirali Akbar Yavari, Ilhami Gulcin, Ertan Sahin, and Abdullah Menzek. "Synthesis and biological evaluation of bromophenol derivatives with cyclopropyl moiety: Ring opening of cyclopropane with monoester." Bioorganic Chemistry 89 (August 2019): 103017. http://dx.doi.org/10.1016/j.bioorg.2019.103017.

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11

Krause, Janina. "Indolizidines from Actinomycetes: An Overview of Producers, Biosynthesis and Bioactivities." Microorganisms 12, no. 7 (2024): 1445. http://dx.doi.org/10.3390/microorganisms12071445.

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Indolizidines have long been recognized for their valuable bioactivities, their common feature being a bicyclic structure connected via a nitrogen atom. Traditionally, plants have been identified as the primary producers. However, recent discoveries have revealed that certain bacterial strains belonging to the genus of actinomycetes also possess the ability to synthesize various indolizidine-based compounds. Among these strains, Streptomyces sp. HNA39, Saccharopolyspora sp. RL78, and Streptomyces NCIB 11649 have been identified as producers of cyclizidines, characterized by their distinctive c

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12

Sydorenko, Ivan, Serhii Holota, Andrii Lozynskyi, et al. "2-(Cyclopropylamino)-5-(4-methoxybenzylidene)thiazol-4(5H)-one." Molbank 2022, no. 4 (2022): M1478. http://dx.doi.org/10.3390/m1478.

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Multicomponent reactions effectively contribute to modern organic and medicinal chemistry. 4-Thiazolidinone core and cyclopropyl moiety are important structural motifs for design of potential biologically active molecules. In the present paper, the convenient step-economy and cost-effective synthesis of 2-(cyclopropylamino)-5-(4-methoxybenzylidene)thiazol-4(5H)-one (2) is described based on the application of the MCR methodology. The proposed approach includes direct one-pot interaction of 2-thioxothiazolidin-4-one (rhodanine), 4-methoxybenzaldehyde with cyclopropylamine which was used in 10%

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13

Kam, Toh-Seok, K. Yoganathan, and Cheng-Hock Chuah. "Lundurines A, B and C, new indole alkaloids with a novel carbon skeleton containing a cyclopropyl moiety." Tetrahedron Letters 36, no. 5 (1995): 759–62. http://dx.doi.org/10.1016/0040-4039(94)02361-e.

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14

KRATZEL, M. "ChemInform Abstract: Synthesis of a C-Nor-morphin-6-ene by Radicalic Isomerization of a Cyclopropyl Moiety." ChemInform 25, no. 45 (2010): no. http://dx.doi.org/10.1002/chin.199445226.

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15

Jun, Joonhong, Jihyun Baek, Songyi Yang та ін. "Discovery of a Potent and Selective JNK3 Inhibitor with Neuroprotective Effect Against Amyloid β-Induced Neurotoxicity in Primary Rat Neurons". International Journal of Molecular Sciences 22, № 20 (2021): 11084. http://dx.doi.org/10.3390/ijms222011084.

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As members of the MAPK family, c-Jun-N-terminal kinases (JNKs) regulate the biological processes of apoptosis. In particular, the isoform JNK3 is expressed explicitly in the brain at high levels and is involved in the pathogenesis of neurodegenerative diseases such as Alzheimer’s disease (AD) and Parkinson’s disease (PD). In this study, we prepared a series of five 6-dihydroxy-1H-benzo[d]imidazoles as JNK3 inhibitors and found them have potential as neuroprotective agents. Following a previous lead scaffold, benzimidazole moiety was modified with various aryl groups and hydroxylation, and the

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16

Krečmerová, Marcela, Milena Masojídková, and Antonín Holý. "Preparation of C-5 Substituted Cidofovir Derivatives." Collection of Czechoslovak Chemical Communications 71, no. 4 (2006): 579–94. http://dx.doi.org/10.1135/cccc20060579.

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1-[(S)-3-Hydroxy-2-(phosphonomethoxy)propyl]cytosine (HPMPC, cidofovir) was modified by substitution on the base moiety in positions C-5 and N4. Key intermediates of these syntheses, diisopropyl esters of (S)-1-[2-(phosphonomethoxy)-3-(triphenylmethoxy)propyl]-5-alkylcytosines (6 and 7) prepared from 5-alkyl-4-methoxypyrimidin-2(1H)-ones were transformed to the corresponding 5-substituted cytosine or N4-alkylcytosine derivatives by the action of ammonia or primary amines, respectively. These fully protected phosphonate esters gave by treatment with bromotrimethylsilane followed by hydrolysis f

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17

KAM, T. S., K. YOGANATHAN, and C. H. CHUAH. "ChemInform Abstract: Lundurines A, B and C, New Indole Alkaloids with a Novel Carbon Skeleton Containing a Cyclopropyl Moiety." ChemInform 26, no. 23 (2010): no. http://dx.doi.org/10.1002/chin.199523221.

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18

Gharia, Bhavini K., Bhanubhai N. Suhagia, and Vineet Jain. "Synthesis, crystal structure studies, characterization and study of novel heterocyclic thiadiazoles as caspase 3 inhibitors for anticancer activity." International Journal of Pharmaceutical Chemistry and Analysis 10, no. 4 (2023): 268–75. http://dx.doi.org/10.18231/j.ijpca.2023.045.

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In the present study we have reported the synthesis of some novel heterocyclic derivatives comprising imidazole and 1,3,4-thiadiazole containing cyclopropyl moiety. Imidazothiadiazoles are of interest because of their diverse biological activities and clinical applications. Primarily docking studies are carried out with reference structure Pdb code:2DKO. We have reported the new series of 5,6 diaryl substituted with imidazo[2,1- b], , thiadiazoles analogs to target caspase family cysteine proteases. The reaction was monitored by Thin-layer chromatography using suitable mobile phase. The Rf val

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19

Pandey, Alka, Aayushi Pandey, Ragini Dubey, Ravi Kant, and Jaya Pandey. "Synthesis and computational studies of potent antimicrobial and anticancer indolone scaffolds with spiro cyclopropyl moiety as a novel design element." Journal of the Indian Chemical Society 99, no. 7 (2022): 100539. http://dx.doi.org/10.1016/j.jics.2022.100539.

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20

Kam, Toh-Seok, Kuan-Hon Lim, K. Yoganathan, Masahiko Hayashi, and Kanki Komiyama. "Lundurines A–D, cytotoxic indole alkaloids incorporating a cyclopropyl moiety from Kopsia tenuis and revision of the structures of tenuisines A–C." Tetrahedron 60, no. 47 (2004): 10739–45. http://dx.doi.org/10.1016/j.tet.2004.08.091.

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21

Frey, Barbara, Lewis N. Mander, and David C. R. Hockless. "Ether formation by intramolecular attack of hydroxy on cyclopropyl rings: a model for the formation of the tetrahydrofuran moiety in the diterpenoid, harringtonolide." Journal of the Chemical Society, Perkin Transactions 1, no. 9 (1998): 1555–60. http://dx.doi.org/10.1039/a800099i.

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22

Thomson, Paul J., Patricia T. Illing, John Farrell, et al. "Modification of the cyclopropyl moiety of abacavir provides insight into the structure activity relationship between HLA‐B*57:01 binding and T‐cell activation." Allergy 75, no. 3 (2019): 636–47. http://dx.doi.org/10.1111/all.14057.

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23

FREY, B., L. N. MANDER, and D. C. R. HOCKLESS. "ChemInform Abstract: Ether Formation by Intramolecular Attack of Hydroxy on Cyclopropyl Rings: A Model for the Formation of the Tetrahydrofuran Moiety in the Diterpenoid, Harringtonolide." ChemInform 29, no. 37 (2010): no. http://dx.doi.org/10.1002/chin.199837212.

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24

Kordes, Markus, Harald Winsel, and Armin de Meijere. "ChemInform Abstract: Cyclopropyl Building Blocks for Organic Synthesis. Part 58. A New Short Access to Amino Acids Incorporating an Aminocyclopropyl Moiety from N,N-Dibenzylcarboxamides." ChemInform 32, no. 5 (2001): no. http://dx.doi.org/10.1002/chin.200105170.

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25

Schinkmanová, Markéta, Ivan Votruba, Riri Shibata, et al. "Human N6-Methyl-AMP/DAMP Aminohydrolase (Abacavir 5'-Monophosphate Deaminase) is Capable of Metabolizing N6-Substituted Purine Acyclic Nucleoside Phosphonates." Collection of Czechoslovak Chemical Communications 73, no. 2 (2008): 275–91. http://dx.doi.org/10.1135/cccc20080275.

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Recombinant human abacavir monophosphate deaminase (hABC-MP deaminase) was compared with the recently described ratN6-methyl-AMP (meAMP) aminohydrolase. hABC-MP deaminase, a 42 kDa polypeptide, exists predominantly as a monomer under non-denaturing conditions. Similar to the rat enzyme, hABC-MP deaminase efficiently catalyzes the hydrolytic deamination of natural substrates meAMP (5),N6,N6-dimethyl-AMP (13) and medAMP (6). Acyclic nucleoside phosphonate (ANP)N6-cyclopropyl-2,6-diamino-9-[2-(phosphonomethoxy)ethyl]purine (cPrPMEDAP) (1), an intermediate intracellular metabolite of antileukemic

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26

Buckheit, Robert W., Tracy L. Hartman, Karen M. Watson, et al. "The Structure-Activity Relationships of 2,4(1H,3H)-pyrimidinedione Derivatives as potent HIV type 1 and type 2 inhibitors." Antiviral Chemistry and Chemotherapy 18, no. 5 (2007): 259–75. http://dx.doi.org/10.1177/095632020701800502.

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Since the discovery of the 2,4 (1 H,3 H)-pyrimidinediones as potent non-nucleoside inhibitors of the HIV-1 reverse transcriptase (RT) this class of compounds has yielded a number of N-1 acyclic substituted pyrimidinediones with substantial antiviral activity, which is highly dependent upon their molecular fit into the binding pocket common to this inhibitory class. We have specifically examined the structure activity relationships of compounds with chemical modification made by substituting homocyclic rather than acyclic moieties at N-1 of the pyrimidinedione. Seventy-four compounds were synth

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27

Husain, S. Shaukat, Ervin Pejo, Rile Ge, and Douglas E. Raines. "Modifying Methoxycarbonyl Etomidate Inter-Ester Spacer Optimizes In Vitro Metabolic Stability and In Vivo Hypnotic Potency and Duration of Action." Anesthesiology 117, no. 5 (2012): 1027–36. http://dx.doi.org/10.1097/aln.0b013e31826d3bef.

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Background Methoxycarbonyl etomidate is the prototypical very rapidly metabolized etomidate analog. Initial studies suggest that it may be too short acting for many clinical uses. We hypothesized that its duration of action could be lengthened and clinical utility broadened by incorporating specific aliphatic groups into the molecule to sterically protect its ester moiety from esterase-catalyzed hydrolysis. To test this hypothesis, we developed a series of methoxycarbonyl etomidate analogs (spacer-linked etomidate esters) containing various aliphatic-protecting groups and spacer lengths. Metho

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28

Król, Małgorzata, Paweł Żmudzki, Adam Bucki, and Agata Kryczyk-Poprawa. "Photodegradation Assessment of Calcipotriol in the Presence of UV Absorbers by UHPLC/MSE." Applied Sciences 15, no. 15 (2025): 8124. https://doi.org/10.3390/app15158124.

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Calcipotriol, a synthetic vitamin D3 analogue widely used in psoriasis treatment, requires a detailed stability assessment due to its topical application and potential exposure to UV radiation. As a drug applied directly to the skin, calcipotriol is particularly susceptible to photodegradation, which may affect its therapeutic efficacy and safety profile. The present study focuses on the analysis of calcipotriol photostability. An advanced UHPLC/MSE method was employed for the precise determination of calcipotriol and its degradation products. Particular attention was given to the effects of c

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29

Birkus, Gabriel, Nilima Kutty, Christian R. Frey, et al. "Role of Cathepsin A and Lysosomes in the Intracellular Activation of Novel Antipapillomavirus Agent GS-9191." Antimicrobial Agents and Chemotherapy 55, no. 5 (2011): 2166–73. http://dx.doi.org/10.1128/aac.01603-10.

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ABSTRACTGS-9191, a bis-amidate prodrug of the nucleotide analog 9-(2-phosphonylmethoxyethyl)-N6-cyclopropyl-2,6-diaminopurine (cPrPMEDAP), was designed as a topical agent for the treatment of papillomavirus-associated proliferative disorders, such as genital warts. In this study, we investigated the mechanism of conversion of GS-9191 to cPrPMEDAP. We observed that GS-9191 is hydrolyzed in the presence of the lysosomal carboxypeptidase cathepsin A (CatA)in vitroand is less efficiently metabolized in CatA-deficient fibroblasts than in control cells. In addition, knockdown of CatA by small interf

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30

Gargallo-Viola, Domingo, Santiago Ferrer, Encarna Tudela, et al. "Antibacterial Activities and Pharmacokinetics of E-4767 and E-5065, Two New 8-Chlorofluoroquinolones with a 7-Azetidin Ring Substituent." Antimicrobial Agents and Chemotherapy 45, no. 11 (2001): 3113–21. http://dx.doi.org/10.1128/aac.45.11.3113-3121.2001.

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ABSTRACT E-4767 {(−)-7-[3-(R)-amino-2-(S)-methyl-1-azetidinyl]-8-chloro-1-cyclopropyl-1,4-dihydro-6-fluoro-4- oxo-3-quinolinecarboxylic acid} and E-5065 [(−)-7-(3-amino-1-azetidinyl)-8-chloro-1-cyclopropyl-1,4-dihydro-6-fluoro-4-oxo-3-quinolinecarboxylic acid] are two new chlorofluoroquinolones with an azetidine moiety at position 7. Their in vitro activities were evaluated in comparison with those of ciprofloxacin, ofloxacin, fleroxacin, and tosufloxacin, while ciprofloxacin was used as a reference for in vivo studies. Against gram-positive organisms, E-4767 and E-5065 were, in general, eight

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31

SAITO, Katsuhiro, Hiroshi FUSHIHARA, Kensuke TAKAHASHI, and Noritaka ABE. "Reactions of Carbene Conjugated with 1-Azaazulene Moiety. Additions of 3-(2-Chloro-1-azaazulenyl)methylene with cis- and trans-Stilbenes and p-Sbustituted Styrenes to Form 3-Cyclopropyl-1-azaazulenes." CHEMICAL & PHARMACEUTICAL BULLETIN 41, no. 4 (1993): 752–54. http://dx.doi.org/10.1248/cpb.41.752.

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SAITO, K., H. FUSHIHARA, K. TAKAHASHI, and N. ABE. "ChemInform Abstract: Reactions of Carbene Conjugated with 1-Azaazulene Moiety: Additions of 3-(2-Chloro-1-azaazulenyl)methylene with cis- and trans-Stilbenes and p-Substituted Styrenes to Form 3-Cyclopropyl-1-azaazulenes." ChemInform 26, no. 6 (2010): no. http://dx.doi.org/10.1002/chin.199506136.

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Titov, Alexander A., Maxim S. Kobzev, Tatiana N. Borisova, et al. "Unusual Transformations of Cyclic Allenes with an Enamine Moiety into Complex Frameworks." Synlett 31, no. 07 (2020): 672–76. http://dx.doi.org/10.1055/s-0039-1691586.

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The thermolysis reactions of benzoazacyclodecatrienes under microwave irradiation conditions in toluene at 150 °C afforded complex azabenzo[a]cyclopropa[cd]azulene and (epiminomethano)cyclopenta[a]indene frameworks. Cyclopropanes were established as intermediates of the ultimate thermolysis products.

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Eckert-Maksic, Mirjana, and Zoran Glasovac. "Cycloproparenyl anions: From models to real systems." Pure and Applied Chemistry 77, no. 11 (2005): 1835–50. http://dx.doi.org/10.1351/pac200577111835.

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An overview of our recent work on cycloproparenyl anions is given. Preparation, the electronic structure, and the properties of the progenitor of the series, cyclopropabenzenyl anion, are discussed. It is shown that the cyclopropabenzenyl anion is by ca. 145 kJ mol-1 more stable than the parent cyclopropenyl anion according to results of the MP2/6-31+G(d) calculations. This finding was attributed to a delicate balance of two opposing effects: (a) propensity of the aromatic ring to alleviate unfavorable 4π electron interaction within the three-membered ring by the anionic resonance effect and (

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35

Khan, Anwar A. "Induction of Dormancy in Nondormant Seeds." Journal of the American Society for Horticultural Science 119, no. 3 (1994): 408–13. http://dx.doi.org/10.21273/jashs.119.3.408.

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A gibberellic acid (GA) biosynthesis inhibitor, tetcyclacis, induced dormancy in nondormant seeds of lettuce (Lactuca sativa L.), tomato (Lycopersicon esculentum Mill.), pepper (Capsicum annuum L.), carrot [Daucus carota var. sativus (Hoffn.)], onion (Allium cepa L.), celery (Apium graveolens L.), and impatiens (Impatiens novette), as most of the seeds failed to germinate after washing under conditions that permitted germination before dormancy induction. In lettuce seeds, tetcyclacis and paclobutrazol were more effective in inhibiting germination in light than in darkness. A 16- to 24-h soak

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Lücke, Jürgen, Mohammad Attaulah Khan, and Wolfgang Voelter. "Isolierung und Strukturidentifizierung eines Cyclopropan-haltigen Triterpens aus Euphorbia lactae / Isolation and Structure Identification of a Triterpenoid with a Cyclopropane Moiety from Euphorbia lactae." Zeitschrift für Naturforschung B 40, no. 5 (1985): 702–4. http://dx.doi.org/10.1515/znb-1985-0522.

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37

Hassenrück, Jessica, and Valentin Wittmann. "Cyclopropene derivatives of aminosugars for metabolic glycoengineering." Beilstein Journal of Organic Chemistry 15 (March 4, 2019): 584–601. http://dx.doi.org/10.3762/bjoc.15.54.

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Cyclopropenes have been proven valuable chemical reporter groups for metabolic glycoengineering (MGE). They readily react with tetrazines in an inverse electron-demand Diels–Alder (DAinv) reaction, a prime example of a bioorthogonal ligation reaction, allowing their visualization in biological systems. Here, we present a comparative study of six cyclopropene-modified hexosamine derivatives and their suitability for MGE. Three mannosamine derivatives in which the cyclopropene moiety is attached to the sugar by either an amide or a carbamate linkage and that differ by the presence or absence of

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38

Dai, Qing-Song, Jun-Long Li, Qi-Wei Wang, et al. "Sulphur ylide-mediated cyclopropanation and subsequent spirocyclopropane rearrangement reactions." Organic & Biomolecular Chemistry, 2022. http://dx.doi.org/10.1039/d2ob00466f.

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A formal (2 + 1) annulation and three-component (1 + 1 + 1) cascade cyclisation via sulphur ylide cyclopropanation under mild conditions is described, with the spiro-cyclopropyl iminoindoline moiety transformed into pyrrolo[3,4-c]quinoline through a novel rearrangement process.

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Kodimuthali, Arumugam, Padala Lakshmi Prasunamba, and Manojit Pal. "Synthesis of a novel analogue of DPP-4 inhibitor Alogliptin: Introduction of a spirocyclic moiety on the piperidine ring." Beilstein Journal of Organic Chemistry 6 (July 1, 2010). http://dx.doi.org/10.3762/bjoc.6.71.

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We report the synthesis of a novel analogue of Alogliptin via condensation of two key intermediates one of which is an aminopiperidine derivative bearing a spirocyclic ring on the piperidine moiety. Preparation of the aminopiperidine intermediate was carried out by constructing the cyclopropyl ring prior to assembling the piperidine ring.

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Li, Feng, Hai Ma, Qing-he Zhao, et al. "An Efficient Substrate-Induced Method for the Synthesis of CF3-Substituted Cyclopropanes by Metal-Free Reaction of Trifluoromethyl Styrylisoxazoles with Nitromethane." Synthesis, November 19, 2020. http://dx.doi.org/10.1055/s-0040-1705976.

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AbstractA series of (trifluoromethyl)cyclopropanes (TFCPs) tolerating a broad range of functional groups, known as tert-butyl bioisosteres, have been obtained from the cyclization reaction between nitromethane and 5-[β-(trifluoromethyl)styryl]isoxazoles in 70–94% yields and 75:25 to 90:10 dr. This method offers practical access to this cyclopropyl moiety of pharmacological interest, employing an inorganic base under phase-transfer conditions.

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Zhang, Zhao‐Yuan, Shu‐Tong Han, Wei Mingyu, et al. "Synthesis and Characterization of Thiazole Derivatives as Cholinesterase Inhibitors." ChemistrySelect 10, no. 11 (2025). https://doi.org/10.1002/slct.202500051.

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AbstractFifteen new thiazole derivatives were synthesized and their cholinesterase inhibitory activities were evaluated. The design of these compounds involves linking thiazole rings to a cyclopropyl moiety, followed by substitutions with various amine groups. The structures of the synthesized thiazole‐cyclopropyl compounds were confirmed using IR, HRMS, ¹H‐NMR, ¹3C‐NMR, HPLC, and single‐crystal X‐ray diffraction. Compounds 6g and 6h were found to crystallize in a monoclinic system with space group P21/c, featuring α and γ angles of 90°. Cholinesterase inhibition was assessed using the Ellman

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Enders, Lukas, Riccardo Mobili, Louis Fensterbank, Juho Heleja, and Virginie Mouriès Mansuy. "Your Invitation to contribute to Chem. Eur. J.Bifunctional Chiral ImPy‐Carbene Ligands. H‐Bonding Controlled Reactivity and Enantioselectivity in Au(I)‐Catalysis." Chemistry – A European Journal, May 13, 2025. https://doi.org/10.1002/chem.202501259.

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Bifunctional chiral N‐heterocyclic carbene ligands have been devised for enantioselective gold(I) catalysis. Based on a single C‐stereogenic center derived from chiral pool α‐aminoacids and connecting an imidazopyridine core to an arylurea motif, enantioselective gold(I)‐catalyzed cycloisomerization reactions could be achieved. High enantioselectivities were notably observed for substrates presenting a pendant propargyl alcohol on 2‐naphthol and 1,6‐enyne scaffolds. In the latter case, the catalyst shows a high degree of selectivity for the unprecedented 6‐endo‐dig biscyclization of these subs

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Wang, Yu, Yong Zhang, Sheng Wang, Qingfeng Cai, Hongyi Song, and Jixiang Chen. "Discovery and Mechanism of a Nematicide Candidate (W3): A Novel Amide Compound Containing a Cyclopropyl Moiety." Journal of Agricultural and Food Chemistry, March 5, 2024. http://dx.doi.org/10.1021/acs.jafc.3c06696.

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Xu, Wen-Bo, Siqi Li, Chang-Ji Zheng, Yu-Xuan Yang, Changhao Zhang, and Cheng-Hua Jin. "Synthesis and Evaluation of Imidazole Derivatives Bearing Imidazo[2,1,b] [1,3,4]thiadiazole Moiety as Antibacterial Agents." Medicinal Chemistry 19 (September 26, 2023). http://dx.doi.org/10.2174/0115734064248204230919074743.

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aims: The aim of this study is to find compounds with strong antibacterial activity, low cytoxicity and development value. background: Drug-resistant infections kill hundreds of thousands of people around the world every year, causing huge losses to the global economy. In previous work, we found that imidazoles containing tri-methoxy- and pyridine-substituted compounds showed strong antibacterial activity. objective: The purpose of this work was to investigate whether compounds with aromatic heterocyclic, alkoxy, and polycyclic introduced into the central imidazole ring showed better antibacte

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Shishkina, Svitlana V., Igor V. Ukrainets, Irina S. Konovalova, Guido J. Reiss та Natalia I. Voloshchuk. "Racemic and unusual enantiomeric crystal forms of N-cycloalkyl-4-methyl-2,2-dioxo-1H-2λ⁶,1-benzothiazine-3-carboxamides and their biological activity". Zeitschrift für Kristallographie - Crystalline Materials, 30 квітня 2025. https://doi.org/10.1515/zkri-2025-0005.

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Abstract The absence of a stereogenic center in N-cycloalkyl-4-methyl-2,2-dioxo-1H-2λ6,1-benzothiazine-3-carboxamides (cycloalkyl moiety is cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl, cyclooctyl) does not interfere with their ability to be crystallized from the ethanol solution into a centrosymmetric or a non-centrosymmetric space group. The non-centrosymmetric crystals containing opposite conformer of a molecule were obtained using aqueous acetic acid as another solvent. Pairs of enantiomorphic crystals have the same crystal shape and unit cell parameters and can only be re

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Chaidali, Andriani G., Michael A. Terzidis, and Ioannis N. Lykakis. "Nitrocyclopropanes as Valuable Building Blocks in Organic Synthesis and Biology: Exploring the Origin of the Nitro Group." Chemistry – A European Journal, January 30, 2025. https://doi.org/10.1002/chem.202404791.

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Cyclopropane derivatives serve as important building blocks in organic synthesis, due to their three‐membered stretched ring. Nitro‐substituted cyclopropanes (NCPs) represent a special class of donor‐acceptor cyclopropanes (DACs) that contain a strong electron‐withdrawing nitro group as substituent on the cyclopropyl moiety. Due to the versatile nature of the nitro group, which can be converted into other functional azo groups or heterocyclic scaffolds, NCPs are considered important building blocks in the design of complex organic compounds. Herein, the present review is organized in two main

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Mamone, Martina, Giuseppe Gentile, Maurizio Prato, and Giacomo Filippini. "Phenol‐Rich Carbon Dots as Metal‐Free Nano‐Photocatalysts for [3+2] Cycloaddition Reactions." ChemSusChem, April 3, 2025. https://doi.org/10.1002/cssc.202500521.

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Carbon dots are unique carbon‐based nanoparticles with potential applications in the field of photocatalysis. In this context, the proper selection of precursors and synthetic conditions is of paramount importance when tailoring the photocatalytic features of the resulting nanomaterials. Here, we have developed a novel bottom‐up methodology for the preparation of phenol‐rich carbon dots (Ph‐CDs) that allowed us to capitalize on the excellent photoredox properties of surface phenolate anions that can be obtained upon deprotonation of Ph‐CDs. Specifically, in this study Ph‐CDs were used in combi

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Kam, Toh-Seok, Kuan-Hon Lim, K. Yoganathan, Masahiko Hayashi, and Kanki Komiyama. "Lundurines A?D, Cytotoxic Indole Alkaloids Incorporating a Cyclopropyl Moiety from Kopsia tenuis and Revision of the Structures of Tenuisines A?C." ChemInform 36, no. 12 (2005). http://dx.doi.org/10.1002/chin.200512212.

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Lemfack, Marie Chantal, Wolfgang Brandt, Katja Krüger, et al. "Reaction mechanism of the farnesyl pyrophosphate C-methyltransferase towards the biosynthesis of pre-sodorifen pyrophosphate by Serratia plymuthica 4Rx13." Scientific Reports 11, no. 1 (2021). http://dx.doi.org/10.1038/s41598-021-82521-9.

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AbstractClassical terpenoid biosynthesis involves the cyclization of the linear prenyl pyrophosphate precursors geranyl-, farnesyl-, or geranylgeranyl pyrophosphate (GPP, FPP, GGPP) and their isomers, to produce a huge number of natural compounds. Recently, it was shown for the first time that the biosynthesis of the unique homo-sesquiterpene sodorifen by Serratia plymuthica 4Rx13 involves a methylated and cyclized intermediate as the substrate of the sodorifen synthase. To further support the proposed biosynthetic pathway, we now identified the cyclic prenyl pyrophosphate intermediate pre-sod

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Appendino, Giovanni, Maria Grazia Cascio, Sara Bacchiega, et al. "First "hybrid" ligands of vanilloid TRPV1 and cannabinoid CB₂ receptors and non‐polyunsaturated fatty acid‐derived CB₂‐selective ligands." December 30, 2005. https://doi.org/10.1016/j.febslet.2005.12.069.

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12‐Phenylacetyl‐ricinoleoyl‐vanillamide (phenylacetylrinvanil, PhAR, IDN5890), is an ultra‐potent agonist of human vanilloid TRPV1 receptors also endowed with moderate affinity for human cannabinoid CB2 receptors. To improve its CB2 affinity and temper its potency at TRPV1, the modification of the polar headgroup and the lipophilic 12‐acylgroup of PhAR was pursued. Replacement of the vanillyl headgroup of PhAR with various aromatic or alkyl amino groups decreased activity at TRPV1 receptors, although the dopamine, cyclopropylamine, 1′‐(R)‐ and 1′‐(S)‐methyl‐ethanolamine, and ethanolamine deriv

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