(+)-Calanolide A


CAS No. : 142632-32-4

(+)-Calanolide A,142632-32-4
Product Details
For research use only. Not Intended for Therapeutic Use!
Cat No:R025037
Synonyms:(10R,11S,12S)-11,12-Dihydro-12-hydroxy-6,6,10,11-tetramethyl-4-propyl-2H,6H,10H-benzo[1,2-b:3,4-b’:5,6-b’’]tripyran-2-one; [10R-(10α,11β,12α)]-11,12-Dihydro-12-hydroxy-6,6,10,11-tetramethyl-4-propyl-2H,6H,10H-benzo[1,2-b:3,4-b’:5,6-b’’]tripyran-2-one
Molecular Formula:C22H26O5
Molecular Weight:370.445
Target:non-nucleoside reverse transcriptase inhibitor
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Appearance:Solid powder
Purity: > 98%
Cat No:R025037
Cas No:142632-32-4
Product-Name:(+)-Calanolide A
InChI:InChI=1S/C22H26O5/c1-6-7-13-10-15(23)26-21-16(13)20-14(8-9-22(4,5)27-20)19-17(21)18(24)11(2)12(3)25-19/h8-12,18,24H,6-7H2,1-5H3/t11-,12-,18+/m1/s1
InChIKey:NIDRYBLTWYFCFV-FMTVUPSXSA-N
SMILES:CCCC1=CC(=O)OC2=C1C3=C(C=CC(O3)(C)C)C4=C2C(C(C(O4)C)C)O
Calanolide A is a non-nucleoside reverse transcriptase inhibitor potentially for the treatment of HIV infection.

1:In vitro glucuronidation of the primary metabolite of 10-chloromethyl-11-demethyl-12-oxo-calanolide A by human liver microsomes and its interactions with UDP-glucuronosyltransferase substrates. Liu X, Sheng L, Zhao M, Mi J, Liu Z, Li Y.Drug Metab Pharmacokinet. 2015 Feb;30(1):89-96. doi: 10.1016/j.dmpk.2014.09.007. Epub 2014 Oct 5. PMID: 25760535
2:Determination of 10-chloromethyl-11-demethyl-12-oxo-calanolide A in rat plasma using liquid chromatography-tandem mass spectrometry and its application to pharmacokinetics. Sheng L, Zhang Q, Liu Z, Liu X, Wang B, Chen H, Li Y.Biomed Chromatogr. 2014 Dec;28(12):1589-91. doi: 10.1002/bmc.3196. Epub 2014 Apr 24. PMID: 24760543
3:Highly suppressing wild-type HIV-1 and Y181C mutant HIV-1 strains by 10-chloromethyl-11-demethyl-12-oxo-calanolide A with druggable profile. Xue H, Lu X, Zheng P, Liu L, Han C, Hu J, Liu Z, Ma T, Li Y, Wang L, Chen Z, Liu G.J Med Chem. 2010 Feb 11;53(3):1397-401. doi: 10.1021/jm901653e. PMID: 20050672
4:[Anti-HIV activities of HIV-1 reverse transcriptase inhibitor racemic 11-demethyl-calanolide A]. Peng ZG, Chen HS, Wang L, Liu G.Yao Xue Xue Bao. 2008 May;43(5):456-60. Chinese. PMID: 18717330
5:Chemical library and structure-activity relationships of 11-demethyl-12-oxo calanolide A analogues as anti-HIV-1 agents. Ma T, Liu L, Xue H, Li L, Han C, Wang L, Chen Z, Liu G.J Med Chem. 2008 Mar 13;51(5):1432-46. doi: 10.1021/jm701405p. Epub 2008 Feb 20. PMID: 18284187
6:Chemical resolution of +/- -calanolide A, +/- -cordatolide A and their 11-demethyl analogues. Ma T, Gao Q, Chen Z, Wang L, Liu G.Bioorg Med Chem Lett. 2008 Feb 1;18(3):1079-83. Epub 2007 Dec 10. PMID: 18155519
7:The role of Thr139 in the human immunodeficiency virus type 1 reverse transcriptase sensitivity to (+)-calanolide A. Auwerx J, Rodríguez-Barrios F, Ceccherini-Silberstein F, San-Félix A, Velázquez S, De Clercq E, Camarasa MJ, Perno CF, Gago F, Balzarini J.Mol Pharmacol. 2005 Sep;68(3):652-9. Epub 2005 Jun 16. PMID: 15961674 Free Article
8:Concise synthesis of anti-HIV-1 active (+)-inophyllum B and (+)-calanolide A by application of (-)-quinine-catalyzed intramolecular oxo-Michael addition. Sekino E, Kumamoto T, Tanaka T, Ikeda T, Ishikawa T.J Org Chem. 2004 Apr 16;69(8):2760-7. PMID: 15074925
9:Anti-HIV natural product (+)-calanolide A is active against both drug-susceptible and drug-resistant strains of Mycobacterium tuberculosis. Xu ZQ, Barrow WW, Suling WJ, Westbrook L, Barrow E, Lin YM, Flavin MT.Bioorg Med Chem. 2004 Mar 1;12(5):1199-207. PMID: 14980631
10:Safety and pharmacokinetic profile of multiple escalating doses of (+)-calanolide A, a naturally occurring nonnucleoside reverse transcriptase inhibitor, in healthy HIV-negative volunteers. Eiznhamer DA, Creagh T, Ruckle JL, Tolbert DT, Giltner J, Dutta B, Flavin MT, Jenta T, Xu ZQ.HIV Clin Trials. 2002 Nov-Dec;3(6):435-50. PMID: 12501127
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