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909-14-8

909-14-8 | (11r,12s)-12-hydroxy-6,6,10,11-tetramethyl-4-propyl-11,12-dihydro-2h,6h,10h-dipyrano[2,3-f:2',3'-h]chromen-2-one

CAS No: 909-14-8 Catalog No: AG006GFU MDL No:

Product Description

Catalog Number:
AG006GFU
Chemical Name:
(11r,12s)-12-hydroxy-6,6,10,11-tetramethyl-4-propyl-11,12-dihydro-2h,6h,10h-dipyrano[2,3-f:2',3'-h]chromen-2-one
CAS Number:
909-14-8
Molecular Formula:
C22H26O5
Molecular Weight:
370.4388
IUPAC Name:
(16S,17R,18S)-18-hydroxy-10,10,16,17-tetramethyl-6-propyl-3,9,15-trioxatetracyclo[12.4.0.02,7.08,13]octadeca-1(14),2(7),5,8(13),11-pentaen-4-one
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-/m0/s1
InChI Key:
NIDRYBLTWYFCFV-PZROIBLQSA-N
SMILES:
CCCc1cc(=O)oc2c1c1OC(C)(C)C=Cc1c1c2[C@@H](O)[C@H](C(O1)C)C

Properties

Complexity:
666  
Compound Is Canonicalized:
Yes
Covalently-Bonded Unit Count:
1  
Defined Atom Stereocenter Count:
3  
Defined Bond Stereocenter Count:
0
Exact Mass:
370.178g/mol
Formal Charge:
0
Heavy Atom Count:
27  
Hydrogen Bond Acceptor Count:
5  
Hydrogen Bond Donor Count:
1  
Isotope Atom Count:
0
Molecular Weight:
370.445g/mol
Monoisotopic Mass:
370.178g/mol
Rotatable Bond Count:
2  
Topological Polar Surface Area:
65A^2
Undefined Atom Stereocenter Count:
0
Undefined Bond Stereocenter Count:
0
XLogP3:
3.8  

Literature

Title Journal
Chemical library and structure-activity relationships of 11-demethyl-12-oxo calanolide A analogues as anti-HIV-1 agents. Journal of medicinal chemistry 20080313
Coumarins as inhibitors of HIV reverse transcriptase. Current HIV research 20060701
The role of Thr139 in the human immunodeficiency virus type 1 reverse transcriptase sensitivity to (+)-calanolide A. Molecular pharmacology 20050901
Selective inhibition of HIV-1 reverse transcriptase-associated ribonuclease H activity by hydroxylated tropolones. Nucleic acids research 20050101
HIV-1 inhibitory compounds from Calophyllum brasiliense leaves. Biological & pharmaceutical bulletin 20040901
[Progress in HIV non-nucleoside reverse transcriptase inhibitors (NNRTIs)]. Yao xue xue bao = Acta pharmaceutica Sinica 20040801
Concise synthesis of anti-HIV-1 active (+)-inophyllum B and (+)-calanolide A by application of (-)-quinine-catalyzed intramolecular oxo-Michael addition. The Journal of organic chemistry 20040416
Anti-HIV natural product (+)-calanolide A is active against both drug-susceptible and drug-resistant strains of Mycobacterium tuberculosis. Bioorganic & medicinal chemistry 20040301
Recent advances in the development of next generation non-nucleoside reverse transcriptase inhibitors. Current topics in medicinal chemistry 20040101
Recent progress in the development of coumarin derivatives as potent anti-HIV agents. Medicinal research reviews 20030501
Safety and pharmacokinetic profile of multiple escalating doses of (+)-calanolide A, a naturally occurring nonnucleoside reverse transcriptase inhibitor, in healthy HIV-negative volunteers. HIV clinical trials 20020101
Anti-HIV-1 activity of calanolides used in combination with other mechanistically diverse inhibitors of HIV-1 replication. Antiviral chemistry & chemotherapy 20000901
Plant-derived and semi-synthetic calanolide compounds with in vitro activity against both human immunodeficiency virus type 1 and human cytomegalovirus. Antiviral chemistry & chemotherapy 20000101
Unique anti-human immunodeficiency virus activities of the nonnucleoside reverse transcriptase inhibitors calanolide A, costatolide, and dihydrocostatolide. Antimicrobial agents and chemotherapy 19990801
Sensitivity and resistance to (+)-calanolide A of wild-type and mutated forms of HIV-1 reverse transcriptase. Antiviral therapy 19990101
In vitro anti-human immunodeficiency virus (HIV) activity of the chromanone derivative, 12-oxocalanolide A, a novel NNRTI. Bioorganic & medicinal chemistry letters 19980818
Inhibition of human immunodeficiency virus type 1 reverse transcriptase activity by cordatolides isolated from Calophyllum cordato-oblongum. Planta medica 19980601
Highly potent oxathiin carboxanilide derivatives with efficacy against nonnucleoside reverse transcriptase inhibitor-resistant human immunodeficiency virus isolates. Antimicrobial agents and chemotherapy 19970401
Structural analogues of the calanolide anti-HIV agents. Modification of the trans-10,11-dimethyldihydropyran-12-ol ring (ring C). Journal of medicinal chemistry 19970314
Antiviral activity and mechanism of action of calanolide A against the human immunodeficiency virus type-1. The Journal of pharmacology and experimental therapeutics 19961101
Structure-activity modifications of the HIV-1 inhibitors (+)-calanolide A and (-)-calanolide B. Journal of medicinal chemistry 19961025
New pyranocoumarins isolated from Calophyllum lanigerum and Calophyllum teysmannii. Journal of natural products 19960801
Synthesis, chromatographic resolution, and anti-human immunodeficiency virus activity of (+/-)-calanolide A and its enantiomers. Journal of medicinal chemistry 19960315
Specific inhibition of the reverse transcriptase of human immunodeficiency virus type 1 and the chimeric enzymes of human immunodeficiency virus type 1 and type 2 by nonnucleoside inhibitors. Antimicrobial agents and chemotherapy 19930501
Analysis of nonnucleoside drug-resistant variants of human immunodeficiency virus type 1 reverse transcriptase. Journal of virology 19930401
The calanolides, a novel HIV-inhibitory class of coumarin derivatives from the tropical rainforest tree, Calophyllum lanigerum. Journal of medicinal chemistry 19920724

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