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(+)-calanolide A

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Origin: China

CasNo: 142632-32-4

specification: 99%min

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  • Products Specification
  • Description
  • Property

    CAS No.: 142632-32-4 Formula: C22H26O5 Molecular Weight: 370.43900

    Description

    Calanolide A is an experimental non-nucleoside reverse transcriptase inhibitor (NNRTI) first acquired from the Calophyllum lanigerum, variety austrocoriaceum, trees in the Malaysian state of Sarawak by botanist John Burley in 1987. The U.S. National Cancer Institute tested calanolide A as a possible cancer treatment, but had no effect. It was later found to have potent anti-HIV activity. On return trip to Malaysia, it was found that all of the austrocoriaceum variety tree species of Calophyllum lanigerum had been cut down most likely for fuel and building material in the swamp forest near Lundu where the first tree samples were taken; however, a few existing species were eventually located in the Singapore Botanic Garden. Since the plant source is relatively rare, a total synthesis was developed in 1996. The form in current use is formulated for oral administration and produced by Sarawak MediChem in Lemont, Illinois.
    Calanolide A is unique among NNRTIs in that it may bind two distinct sites in reverse transcriptase.

    Basic Info

    Chemical Name (+)-calanolide A
    Synonyms

    CALANOLIDE A;
    (+)-(10R,11S,12S)-12-HYDROXY-6,6,10,11-TETRAMETHYL-4-PROPYL-11,12-DIHYDRO-2H,6H,10H-BENZO(1,2-B:3,4-B':5,6-B'']TRIPYRAN-2-ONE;
    calanolide-A;

    CAS No. 142632-32-4
    Molecular Formula C22H26O5
    Molecular Weight 370.43900
    PSA 68.90000
    LogP 4.38010

    Properties

    Density 1.181g/cm3
    Boiling Point 514.8ºC at 760mmHg
    Flash Point 177.2ºC
    Refractive Index 1.558
    Vapor Pressure 2E-11mmHg at 25°C

    Synthesis Route

    HI-D86(+)-Calanolide B+(+)-calanolide A
    (2R,3R,4S)-2,3,10,10-tetramethyl-6-oxo-8-propyl-3,4-dihydro-2H,6H,10H-dipyrano[2,3-f:2',3'-h]chromen-4-yl 2-(((1R,2S,5R)-2-isopropyl-5-methylcyclohexyl)oxy)acetate(+)-calanolide A
    HI-D86(+)-calanolide A

    Precursor

    (9S)-5-hydroxy-8,9-dimethyl-4-propyl-8,9-dihydro-2H,10H-pyrano[2,3-f]chromene-2,10-dione
    5-hydroxy-2,2-dimethyl-10-propyl-6-propionyl-2H,8H-pyrano[2,3-f]chromen-8-one
    HI-D86
    (2R,3R,4S)-2,3,10,10-tetramethyl-6-oxo-8-propyl-3,4-dihydro-2H,6H,10H-dipyrano[2,3-f:2',3'-h]chromen-4-yl 2-(((1R,2S,5R)-2-isopropyl-5-methylcyclohexyl)oxy)acetate

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