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Chemical Compound Review

Cyclopropyl     cyclopropane

Synonyms: AC1L3VZL, DNC000502, AR-1I3354, AC1Q1GU5, 2417-82-5, ...
 
 
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Disease relevance of cyclopropane

 

High impact information on cyclopropane

  • For the compounds with an intact cyclopropyl group, the order of cytotoxic and mutagenic potency (molar basis) in V79 cells generally correlated with binding to calf thymus DNA, and increased with the length of the B segment [6].
  • Plants and certain protists use cycloeucalenol cycloisomerase (EC ) to convert pentacyclic cyclopropyl sterols to conventional tetracyclic sterols [7].
  • Highly stereoselective prins cyclization of silylmethyl-substituted cyclopropyl carbinols to 2,4,6-trisubstituted tetrahydropyrans [8].
  • Incubation of 2b with PB microsomes resulted in p-hydroxylation and N-demethylation only; no loss or ring-opening of the cyclopropyl group occurred [9].
  • N-dealkylation of an N-cyclopropylamine by horseradish peroxidase. Fate of the cyclopropyl group [10].
 

Chemical compound and disease context of cyclopropane

  • Hepatitis C virus NS3-4A serine protease inhibitors: use of a P2-P1 cyclopropyl alanine combination for improved potency [11].
  • The potential antitumor activity of a series of novel cyclopropyl compounds, which lack estrogen agonist activity, was evaluated in estrogen receptor positive human breast cancer cells (MCF-7) in culture [12].
  • These data show that in broad terms the cytotoxic potency of bisamidines 1-3 in the cultured breast cancer MCF-7 cells decreases with the size of the alkyl group substituent (cyclopropyl > isopropyl > cyclopentyl), in accord with their increases in DNA affinity, as shown by the binding constant values [13].
  • Analog II (1,1-dichloro-cis-2,3-diaryl cyclopropane) is a cyclopropyl compound which produces pure antiestrogenic activity in mice and inhibits the proliferation of breast cancer cells [14].
  • Using the gas chromatography-mass spectrometry (GC-MS) method we found in Streptomyces cinnamonensis saturated fatty acids of iso- and anteiso- types, cyclopropyl acids, and unsaturated fatty acids where the double bond position was determined by MS of their pyrrolidine derivatives [15].
 

Biological context of cyclopropane

  • Other cyclizations of alkynes with furans or electron-rich arenes give products of apparent Friedel-Crafts-type reactions, although these processes could also proceed by pathways involving the formation of cyclopropyl platinum carbenes [16].
  • It has been postulated that metabolism via hydrogenation of the 8,9-double bonds of these molecules would unmask the electrophilic, and thus, the toxic nature of their cyclopropyl moieties [17].
  • Cytochrome P450 hydroxylation of hydrocarbons: variation in the rate of oxygen rebound using cyclopropyl radical clocks including two new ultrafast probes [18].
  • The influence on the structure-activity relationships of varied substituents at C8 (H, F, Cl) and N1 (ethyl, cyclopropyl, difluorophenyl) was also studied [19].
  • Hydrolysis rates in aqueous buffered solution do not differ significantly in the allyl- and cyclopropyl series [20].
 

Anatomical context of cyclopropane

  • This fatty acid, containing a cyclopropyl moiety in the beta,gamma-position, was designed to enter the myocardium by the same mechanism as natural fatty acids and to undergo partial metabolism before being trapped in the cell [21].
  • Its structure is unique in that it contains the sequential positioning of a thiazoline and cyclopropyl ring, and it exerts its potent cell toxicity through interaction with the colchicine drug binding site on microtubules [22].
  • These are the first reported cyclopropyl-containing fatty acid derivatives from a Lyngbya sp. Grenadadiene (1) has an interesting profile of cytotoxicity in the NCI 60 cell line assay, while grenadamide (2) exhibited modest brine shrimp toxicity (LD50 = 5 microg/mL) and cannabinoid receptor binding activity (Ki = 4.7 microM) [23].
 

Associations of cyclopropane with other chemical compounds

  • Modifications favorable for binding affinity are (1). a thiomethyl group at C21 of the thiazole side chain, (2). a methyl group at C12 in S configuration, (3). a pyridine side chain with C15 in S configuration, and (4). a cyclopropyl moiety between C12 and C13 [24].
  • Since the cyclopropyl ketone derivative 14 (ciproxifan) had high affinity in vitro as well as high potency in vivo, it was selected for further studies in monkeys [25].
  • Reaction of enol ethers with alkynes catalyzed by transition metals: 5-exo-dig versus 6-endo-dig cyclizations via cyclopropyl platinum or gold carbene complexes [26].
  • The quinolone structure-activity relationship demonstrated here shows that C-8, the C-7 ring, the C-6 fluorine, and the N-1 cyclopropyl substituents are desirable structural features in targeting M. tuberculosis gyrase [27].
  • To clarify the structure-activity relationship of the sugar moiety, various 3'-C-carbon-substituted analogues, such as 1-propynyl, 1-butynyl, ethenyl, ethyl, and cyclopropyl derivatives, of ECyd and EUrd were synthesized [28].
 

Gene context of cyclopropane

  • These results indicate that the relative configuration of the cyclopropyl ring in the L-arginine analogues significantly affects their inhibitory potential and NOS isoform selectivity [29].
  • Structure-activity relationships are used to optimize the affinity of various acyl guanidines for NHE-1 by screening the effect of substituents at both aryl and cyclopropyl rings [30].
  • In this paper, we describe the characterization of the novel cyclopropyl-substituted product analogue 4'-phospho-N-(1-mercaptomethyl-cyclopropyl)-pantothenamide (PPanDeltaSH) as a mechanism-based inhibitor of the human PPC-DC enzyme [31].
  • Enantioselective binding of an 11-cis-locked cyclopropyl retinal. The conformation of retinal in bovine rhodopsin [32].
  • These values show that the tert-butyl substituent is at least as good as cyclopropyl in rendering high levels of antimycobacterial activity [33].
 

Analytical, diagnostic and therapeutic context of cyclopropane

  • This novel C-3' substituted carboxy cyclopropyl glycine is a highly potent group 2 and group 3 mGluR agonist that has proven to be orally active in both fear potentiated startle (animal model for anxiety) and PCP-induced motor activation (animal model for psychosis) assays in rats [34].
  • Monitoring by HPLC, the azaCBI ligand in the Co(III)(cyclen)(azaCBI) complex (2) slowly hydrolysed in aqueous solution, in contrast to the free ligand 1 which readily converted to its reactive cyclopropyl form [35].
  • Gas chromatography coupled to mass spectrometry analyses of methanolyzed lipidic extracts from tissues incubated with each probe revealed that all the cyclopropyl fatty acids were transformed into the corresponding 11-cyclopropylidene acids, except for compound trans-5 (5b), which was not desaturated at C11 [36].
  • The molecular structures of the 2-bromo-3-cyclopropyl-1-phosphapropene, 1,2-bis(cyclopropyl)-3,4-diphosphinidenecyclobutene and the digold complex were unambiguously determined by X-ray crystallography and are discussed from the point of view of the cyclopropyl conjugation [37].

References

  1. A common mechanism for the biosynthesis of methoxy and cyclopropyl mycolic acids in Mycobacterium tuberculosis. Yuan, Y., Barry, C.E. Proc. Natl. Acad. Sci. U.S.A. (1996) [Pubmed]
  2. Mycobacterium bovis BCG genes involved in the biosynthesis of cyclopropyl keto- and hydroxy-mycolic acids. Dubnau, E., Lanéelle, M.A., Soares, S., Bénichou, A., Vaz, T., Promé, D., Promé, J.C., Daffé, M., Quémard, A. Mol. Microbiol. (1997) [Pubmed]
  3. Chemical evolution of the fluoroquinolone antimicrobial agents. Neu, H.C. Am. J. Med. (1989) [Pubmed]
  4. Characterization of lipid fatty acids in whole-cell microorganisms using in situ supercritical fluid derivatization/extraction and gas chromatography/mass spectrometry. Gharaibeh, A.A., Voorhees, K.J. Anal. Chem. (1996) [Pubmed]
  5. Synthesis and antiviral activity of novel acyclic nucleosides: discovery of a cyclopropyl nucleoside with potent inhibitory activity against herpesviruses. Sekiyama, T., Hatsuya, S., Tanaka, Y., Uchiyama, M., Ono, N., Iwayama, S., Oikawa, M., Suzuki, K., Okunishi, M., Tsuji, T. J. Med. Chem. (1998) [Pubmed]
  6. Mutagenicity of the antitumor antibiotic CC-1065 and its analogues in mammalian (V79) cells and bacteria. Harbach, P.R., Zimmer, D.M., Mazurek, J.H., Bhuyan, B.K. Cancer Res. (1988) [Pubmed]
  7. Functional cloning of an Arabidopsis thaliana cDNA encoding cycloeucalenol cycloisomerase. Lovato, M.A., Hart, E.A., Segura, M.J., Giner, J.L., Matsuda, S.P. J. Biol. Chem. (2000) [Pubmed]
  8. Highly stereoselective prins cyclization of silylmethyl-substituted cyclopropyl carbinols to 2,4,6-trisubstituted tetrahydropyrans. Yadav, V.K., Kumar, N.V. J. Am. Chem. Soc. (2004) [Pubmed]
  9. Formation of cyclopropanone during cytochrome P450-catalyzed N-dealkylation of a cyclopropylamine. Shaffer, C.L., Harriman, S., Koen, Y.M., Hanzlik, R.P. J. Am. Chem. Soc. (2002) [Pubmed]
  10. N-dealkylation of an N-cyclopropylamine by horseradish peroxidase. Fate of the cyclopropyl group. Shaffer, C.L., Morton, M.D., Hanzlik, R.P. J. Am. Chem. Soc. (2001) [Pubmed]
  11. Hepatitis C virus NS3-4A serine protease inhibitors: use of a P2-P1 cyclopropyl alanine combination for improved potency. Bogen, S., Saksena, A.K., Arasappan, A., Gu, H., Njoroge, F.G., Girijavallabhan, V., Pichardo, J., Butkiewicz, N., Prongay, A., Madison, V. Bioorg. Med. Chem. Lett. (2005) [Pubmed]
  12. Antiproliferative activity of a series of novel cyclopropyl antiestrogens on MCF-7 human breast cancer cells in culture. Jain, P.T., Pento, J.T., Magarian, R.A., Graves, D.C. Anticancer Drugs (1991) [Pubmed]
  13. DNA-binding properties and cytotoxicity of extended aromatic bisamidines in breast cancer MCF-7 cells. Bielawski, K., Wołczyński, S., Bielawska, A. Polish journal of pharmacology. (2001) [Pubmed]
  14. The mutagenic potential of antiestrogens at the HPRT locus in V79 cells. Rajah, T.T., Pento, J.T. Res. Commun. Mol. Pathol. Pharmacol. (1995) [Pubmed]
  15. Fatty acids of Streptomyces cinnamonensis, producer of monensin. Rezanka, T., Klánová, K., Podojil, M., Vanĕk, Z. Folia Microbiol. (Praha) (1984) [Pubmed]
  16. Intramolecular reactions of alkynes with furans and electron rich arenes catalyzed by PtCl2: the role of platinum carbenes as intermediates. Martín-Matute, B., Nevado, C., Cárdenas, D.J., Echavarren, A.M. J. Am. Chem. Soc. (2003) [Pubmed]
  17. NADPH alkenal/one oxidoreductase activity determines sensitivity of cancer cells to the chemotherapeutic alkylating agent irofulven. Dick, R.A., Yu, X., Kensler, T.W. Clin. Cancer Res. (2004) [Pubmed]
  18. Cytochrome P450 hydroxylation of hydrocarbons: variation in the rate of oxygen rebound using cyclopropyl radical clocks including two new ultrafast probes. Atkinson, J.K., Ingold, K.U. Biochemistry (1993) [Pubmed]
  19. Synthesis and biological activity of 5-amino- and 5-hydroxyquinolones, and the overwhelming influence of the remote N1-substituent in determining the structure-activity relationship. Domagala, J.M., Bridges, A.J., Culbertson, T.P., Gambino, L., Hagen, S.E., Karrick, G., Porter, K., Sanchez, J.P., Sesnie, J.A., Spense, F.G. J. Med. Chem. (1991) [Pubmed]
  20. Mutagenic properties of N-cyclopropyl and N-allyl-N-nitroso compounds. Studies on the nature of alkylating species. Wiessler, M., Pool, B.L. Carcinogenesis (1984) [Pubmed]
  21. Evaluation of trans-9-18F-fluoro-3,4-Methyleneheptadecanoic acid as a PET tracer for myocardial fatty acid imaging. Shoup, T.M., Elmaleh, D.R., Bonab, A.A., Fischman, A.J. J. Nucl. Med. (2005) [Pubmed]
  22. Biosynthetic pathway and gene cluster analysis of curacin A, an antitubulin natural product from the tropical marine cyanobacterium Lyngbya majuscula. Chang, Z., Sitachitta, N., Rossi, J.V., Roberts, M.A., Flatt, P.M., Jia, J., Sherman, D.H., Gerwick, W.H. J. Nat. Prod. (2004) [Pubmed]
  23. Grenadadiene and grenadamide, cyclopropyl-containing fatty acid metabolites from the marine cyanobacterium Lyngbya majuscula. Sitachitta, N., Gerwick, W.H. J. Nat. Prod. (1998) [Pubmed]
  24. Interaction of epothilone analogs with the paclitaxel binding site: relationship between binding affinity, microtubule stabilization, and cytotoxicity. Buey, R.M., Díaz, J.F., Andreu, J.M., O'Brate, A., Giannakakou, P., Nicolaou, K.C., Sasmal, P.K., Ritzén, A., Namoto, K. Chem. Biol. (2004) [Pubmed]
  25. Novel histamine H(3)-receptor antagonists with carbonyl-substituted 4-(3-(phenoxy)propyl)-1H-imidazole structures like ciproxifan and related compounds. Stark, H., Sadek, B., Krause, M., Hüls, A., Ligneau, X., Ganellin, C.R., Arrang, J.M., Schwartz, J.C., Schunack, W. J. Med. Chem. (2000) [Pubmed]
  26. Reaction of enol ethers with alkynes catalyzed by transition metals: 5-exo-dig versus 6-endo-dig cyclizations via cyclopropyl platinum or gold carbene complexes. Nevado, C., Cárdenas, D.J., Echavarren, A.M. Chemistry (Weinheim an der Bergstrasse, Germany) (2003) [Pubmed]
  27. Mycobacterium tuberculosis DNA gyrase: interaction with quinolones and correlation with antimycobacterial drug activity. Aubry, A., Pan, X.S., Fisher, L.M., Jarlier, V., Cambau, E. Antimicrob. Agents Chemother. (2004) [Pubmed]
  28. Nucleosides and nucleotides. 175. Structural requirements of the sugar moiety for the antitumor activities of new nucleoside antimetabolites, 1-(3-C-ethynyl-beta-D-ribo-pentofuranosyl)cytosine and -uracil1. Hattori, H., Nozawa, E., Iino, T., Yoshimura, Y., Shuto, S., Shimamoto, Y., Nomura, M., Fukushima, M., Tanaka, M., Sasaki, T., Matsuda, A. J. Med. Chem. (1998) [Pubmed]
  29. Synthesis and evaluation of trans 3,4-cyclopropyl L-arginine analogues as isoform selective inhibitors of nitric oxide synthase. Fishlock, D., Perdicakis, B., Montgomery, H.J., Guillemette, J.G., Jervis, E., Lajoie, G.A. Bioorg. Med. Chem. (2003) [Pubmed]
  30. Arylcyclopropanecarboxyl guanidines as novel, potent, and selective inhibitors of the sodium hydrogen exchanger isoform-1. Ahmad, S., Doweyko, L.M., Dugar, S., Grazier, N., Ngu, K., Wu, S.C., Yost, K.J., Chen, B.C., Gougoutas, J.Z., DiMarco, J.D., Lan, S.J., Gavin, B.J., Chen, A.Y., Dorso, C.R., Serafino, R., Kirby, M., Atwal, K.S. J. Med. Chem. (2001) [Pubmed]
  31. Mechanistic studies on phosphopantothenoylcysteine decarboxylase: trapping of an enethiolate intermediate with a mechanism-based inactivating agent. Strauss, E., Zhai, H., Brand, L.A., McLafferty, F.W., Begley, T.P. Biochemistry (2004) [Pubmed]
  32. Enantioselective binding of an 11-cis-locked cyclopropyl retinal. The conformation of retinal in bovine rhodopsin. Lou, J., Hashimoto, M., Berova, N., Nakanishi, K. Org. Lett. (1999) [Pubmed]
  33. N-1-tert-butyl-substituted quinolones: in vitro anti-Mycobacterium avium activities and structure-activity relationship studies. Klopman, G., Fercu, D., Renau, T.E., Jacobs, M.R. Antimicrob. Agents Chemother. (1996) [Pubmed]
  34. (2S,1'S,2'R,3'R)-2-(2'-Carboxy-3'-hydroxymethylcyclopropyl) glycine is a highly potent group 2 and 3 metabotropic glutamate receptor agonist with oral activity. Collado, I., Pedregal, C., Bueno, A.B., Marcos, A., González, R., Blanco-Urgoiti, J., Pérez-Castells, J., Schoepp, D.D., Wright, R.A., Johnson, B.G., Kingston, A.E., Moher, E.D., Hoard, D.W., Griffey, K.I., Tizzano, J.P. J. Med. Chem. (2004) [Pubmed]
  35. Radiolytic and cellular reduction of a novel hypoxia-activated cobalt(III) prodrug of a chloromethylbenzindoline DNA minor groove alkylator. Ahn, G.O., Botting, K.J., Patterson, A.V., Ware, D.C., Tercel, M., Wilson, W.R. Biochem. Pharmacol. (2006) [Pubmed]
  36. Enzymatic desaturation of fatty acids: delta11 desaturase activity on cyclopropane acid probes. Villorbina, G., Roura, L., Camps, F., Joglar, J., Fabriàs, G. J. Org. Chem. (2003) [Pubmed]
  37. Structural and coordination properties of 1,2-bis(cyclopropyl)-3,4-bis(2,4,6-tri-tert-butylphenyl)-3,4-diphosphinidenecyclobutene prepared by dehydrogenative homocoupling of 3-cyclopropyl-1-(2,4,6-tri-tert-butylphenyl)-1-phosphaallene. Ito, S., Freytag, M., Yoshifuji, M. Dalton transactions (Cambridge, England : 2003) (2006) [Pubmed]
 
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