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Chemical Compound Review

Cyclopentyl     cyclopentane

Synonyms: cyclopentanyl, AC1L3C04, 3889-74-5, 16191-EP2281563A1, 16191-EP2316459A1, ...
 
 
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Disease relevance of cyclopentane

 

High impact information on cyclopentane

 

Chemical compound and disease context of cyclopentane

 

Biological context of cyclopentane

 

Anatomical context of cyclopentane

  • RP 73401 is metabolized by human liver microsomes almost exclusively by transhydroxylation of the cyclopentyl group to RPR 113406 [19].
  • Modulation of human leukocyte histamine release by sn-1,2-isopropylidene-3-decanoyl-glycerol and decanoic acid cyclopentyl methylester in comparison with effects of synthetic diacylglycerols and a phorbol ester [20].
  • In anesthetized rats, DOPA cyclohexyl ester (DOPA CHE), DOPA cyclopentyl ester (DOPA CPE) and DOPA cyclopentyldimethyl ester (DOPA CPDME) at 1 microgram microinjected into depressor sites of the nucleus tractus solitarii elicited or tended to elicit more marked antagonism against depressor responses to 60 ng L-DOPA, compared to DOPA ME [21].
 

Associations of cyclopentane with other chemical compounds

 

Gene context of cyclopentane

  • Reactivation and aging of cyclopentyl methylphosphonylated acetylcholinesterase in the presence of some 1-alkyl-2-hydroxyiminomethyl-pyridinium salts [26].
  • In pathway I, the six-membered transition structure (TS-I) connects the less stable cyclopentyl cation 1A and the 1,2-dimethylcyclohexyl carbocation (2) via a barrier of 16.4 kcal/mol [27].
  • DSC studies reveal the presence of a weak endotherm at -13 degrees C. The structures of the two phases are very similar, differing only in the relative orientations of the cyclopentyl rings of the organic cations and slight displacements of the anionic tetrahedra [28].
  • Similarly, cis-4-hexadecenoic acid and C16 and C18 cyclopentyl fatty acids were identified for the first time in H. anthelmintica [29].
  • The incorporation of the 1-aryl-5-(4-nitrophenyl)-3-oxo-1,4-pentadienyl group into 3,4-dihydro-1H-naphthalenyl, cyclohexyl, 2,3-dihydro-1H-indenyl and cyclopentyl scaffolds led to the discovery of various compounds with selective toxicity for malignant cells and ability to reverse multidrug resistance [30].
 

Analytical, diagnostic and therapeutic context of cyclopentane

  • Antibacterial activity in serum and urine following oral administration in man of DL473 (a cyclopentyl derivative of rifampicin) [proceedings] [31].
  • Cyclopentyl and (+/-)-exo-2-norbornylcarbamates of cellulose and amylose were prepared and their chiral recognition abilities as chiral stationary phases for high-performance liquid chromatography (HPLC) were evaluated [32].

References

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  2. Nonpeptidic potent HIV-1 protease inhibitors: (4-hydroxy-6-phenyl-2-oxo-2H- pyran-3-yl)thiomethanes that span P1-P2' subsites in a unique mode of active site binding. Prasad, J.V., Para, K.S., Tummino, P.J., Ferguson, D., McQuade, T.J., Lunney, E.A., Rapundalo, S.T., Batley, B.L., Hingorani, G., Domagala, J.M. J. Med. Chem. (1995) [Pubmed]
  3. Comparative uptake of rifampicin and rifapentine (DL473) by human neutrophils. Easmon, C.S., Crane, J.P. J. Antimicrob. Chemother. (1984) [Pubmed]
  4. Disposition and metabolism of rifapentine, a rifamycin antibiotic, in mice, rats, and monkeys. Emary, W.B., Toren, P.C., Mathews, B., Huh, K. Drug Metab. Dispos. (1998) [Pubmed]
  5. Effect of rifampin and its cyclopentyl analogue, MDL 473, on the expression of delayed type hypersensitivity to oxazolone. Kenny, M.T. Int. J. Immunopharmacol. (1987) [Pubmed]
  6. Cyclopentyl ketones: identification and function in Azteca ants. Wheeler, J.W., Evans, S.L., Blum, M.S., Torgerson, R.L. Science (1975) [Pubmed]
  7. Glyoxalase I Is Critical for Human Retinal Capillary Pericyte Survival under Hyperglycemic Conditions. Miller, A.G., Smith, D.G., Bhat, M., Nagaraj, R.H. J. Biol. Chem. (2006) [Pubmed]
  8. Pharmacophoric requirements for the cannabinoid side chain. Probing the cannabinoid receptor subsite at C1'. Papahatjis, D.P., Nikas, S.P., Kourouli, T., Chari, R., Xu, W., Pertwee, R.G., Makriyannis, A. J. Med. Chem. (2003) [Pubmed]
  9. New and emerging therapies for pulmonary complications of cystic fibrosis. Tonelli, M.R., Aitken, M.L. Drugs (2001) [Pubmed]
  10. Membrane lipids of mesophilic anaerobic bacteria thriving in peats have typical archaeal traits. Weijers, J.W., Schouten, S., Hopmans, E.C., Geenevasen, J.A., David, O.R., Coleman, J.M., Pancost, R.D., Sinninghe Damsté, J.S. Environ. Microbiol. (2006) [Pubmed]
  11. Characterization of antiviral activity of entecavir in transgenic mice expressing hepatitis B virus. Julander, J.G., Colonno, R.J., Sidwell, R.W., Morrey, J.D. Antiviral Res. (2003) [Pubmed]
  12. Synthesis of carbon-11 labeled sulfonanilide analogues as new potential PET agents for imaging of aromatase in breast cancer. Wang, M., Lacy, G., Gao, M., Miller, K.D., Sledge, G.W., Zheng, Q.H. Bioorg. Med. Chem. Lett. (2007) [Pubmed]
  13. Enhancement of enzyme activity and enantioselectivity by cyclopentyl methyl ether in the transesterification catalyzed by Pseudomonas cepacia lipase co-lyophilized with cyclodextrins. Mine, Y., Zhang, L., Fukunaga, K., Sugimura, Y. Biotechnol. Lett. (2005) [Pubmed]
  14. Pd-catalyzed asymmetric allylic alkylation. A short route to the cyclopentyl core of viridenomycin. Trost, B.M., Jiang, C. Org. Lett. (2003) [Pubmed]
  15. The metabolism of (2-cyclopentyl-6,7-dichloro-2-methyl-1-oxo-5-indanyloxy)acetic acid in chimpanzee and man. Zacchei, A.G., Wishousky, T.I., Arison, B.H., Hitzenberger, G. Drug Metab. Dispos. (1978) [Pubmed]
  16. Attenuation of traumatic cell death by an adenosine A1 agonist in rat hippocampal cells. Mitchell, H.L., Frisella, W.A., Brooker, R.W., Yoon, K.W. Neurosurgery (1995) [Pubmed]
  17. Synthesis and antimicrobial activity of some novel 2,5- and/or 6-substituted benzoxazole and benzimidazole derivatives. Oren, I., Temiz, O., Yalçin, I., Sener, E., Altanlar, N. European journal of pharmaceutical sciences : official journal of the European Federation for Pharmaceutical Sciences. (1999) [Pubmed]
  18. Induction of ovulation and cyclic activity in anestrous ewes with testosterone treated wethers and ewes. Croker, K.P., Butler, L.G., Johns, M.A., McColm, S.C. Theriogenology (1982) [Pubmed]
  19. Human liver CYP2B6-catalyzed hydroxylation of RP 73401. Stevens, J.C., White, R.B., Hsu, S.H., Martinet, M. J. Pharmacol. Exp. Ther. (1997) [Pubmed]
  20. Modulation of human leukocyte histamine release by sn-1,2-isopropylidene-3-decanoyl-glycerol and decanoic acid cyclopentyl methylester in comparison with effects of synthetic diacylglycerols and a phorbol ester. Bergstrand, H., Lundquist, B., Michelsen, P. Allergy (1989) [Pubmed]
  21. L-DOPA cyclohexyl ester is a novel potent and relatively stable competitive antagonist against L-DOPA among several L-DOPA ester compounds. Furukawa, N., Goshima, Y., Miyamae, T., Sugiyama, Y., Shimizu, M., Ohshima, E., Suzuki, F., Arai, N., Fujita, K., Misu, Y. Jpn. J. Pharmacol. (2000) [Pubmed]
  22. Conformational study in water by NMR and molecular modeling of cyclic glutamic acid analogues as probes of vitamin K dependent carboxylase. Larue, V., Gharbi-Benarous, J., Archer, F., Azerad, R., Girault, J.P. Journal of chemical information and computer sciences. (1996) [Pubmed]
  23. Interaction between purinoceptor subtypes on hippocampal serotonergic transmission using in vivo microdialysis. Okada, M., Kawata, Y., Murakami, T., Wada, K., Mizuno, K., Kaneko, S. Neuropharmacology (1999) [Pubmed]
  24. Reversed-phase liquid chromatographic enantioseparation by cycloalkylcarboxylates of cellulose and amylose. Kubota, T., Yamamoto, C., Okamoto, Y. Chirality. (2004) [Pubmed]
  25. Metabolism of a novel phosphodiesterase-IV inhibitor (V11294) by human hepatic cytochrome P450 forms. Subrahmanyam, V., Renwick, A.B., Walters, D.G., Price, R.J., Tonelli, A.P., Lake, B.G. Xenobiotica (2002) [Pubmed]
  26. Reactivation and aging of cyclopentyl methylphosphonylated acetylcholinesterase in the presence of some 1-alkyl-2-hydroxyiminomethyl-pyridinium salts. de Jong, L.P., Wolring, G.Z. Biochem. Pharmacol. (1978) [Pubmed]
  27. Rearrangement pathways of five-membered ring enlargement in carbocations: quantum chemical calculations and deuterium kinetic isotope effects. Vrcek, V., Saunders, M., Kronja, O. J. Org. Chem. (2003) [Pubmed]
  28. Structure and magnetism of a spin ladder system: (C5H9NH3)2CuBr4. Willett, R.D., Galeriu, C., Landee, C.P., Turnbull, M.M., Twamley, B. Inorganic chemistry. (2004) [Pubmed]
  29. Analysis of seed oils containing cyclopentenyl fatty acids by combined chromatographic procedures. Christie, W.W., Brechany, E.Y., Shukla, V.K. Lipids (1989) [Pubmed]
  30. 3-Arylidene-1-(4-nitrophenylmethylene)-3,4-dihydro-1H-naphthalen-2-ones and related compounds displaying selective toxicity and reversal of multidrug resistance in neoplastic cells. Dimmock, J.R., Das, U., Gul, H.I., Kawase, M., Sakagami, H., Baráth, Z., Ocsovsky, I., Molnár, J. Bioorg. Med. Chem. Lett. (2005) [Pubmed]
  31. Antibacterial activity in serum and urine following oral administration in man of DL473 (a cyclopentyl derivative of rifampicin) [proceedings]. Birmingham, A.T., Coleman, A.J., Orme, M.L., Park, B.K., Pearson, N.J., Short, A.H., Southgate, P.J. British journal of clinical pharmacology. (1978) [Pubmed]
  32. Chromatographic enantioseparation by cycloalkylcarbamate derivatives of cellulose and amylose. Kubota, T., Yamamoto, C., Okamoto, Y. Chirality. (2002) [Pubmed]
 
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