Method for the preparation of (+)-calanolide A and analogues the

Organic compounds -- part of the class 532-570 series – Organic compounds – Heterocyclic carbon compounds containing a hetero ring...

Patent

Rate now

  [ 0.00 ] – not rated yet Voters 0   Comments 0

Details

435280, C07D49300

Patent

active

059773855

ABSTRACT:
A method of preparing (+)-calanolide A, 1, a potent HIV reverse transcriptase inhibitor, from chromene 4 is provided. According to the disclosed method, chromene 4 intermediate was subjected to a chlorotitanium-mediated aldol reaction with acetaldehyde to selectively produce (.+-.)-8a. Separation and enzyme-mediated resolution of (.+-.)-8a produced (+)-8a. Cyclization of (+)-8a under neutral Mitsunobu conditions followed by Luche reduction of (+)-7 produced (+)-calanolide A in high yield and enantiomeric purity. The method of the invention has been extended to produce potent antiviral calanolide A analogues.

REFERENCES:
Barton et al. (1990), Tetrahedron Letters, Wol. 31, pp. 7449-7452.
Szell et al. (1969), Helvetica Chimica Acta, vol. 52, pp. 2636-2641.
Fung et al. (1978), J. Org. Chem., vol. 43, pp. 3977-3979.
Gemal et al. (1981), J. Am. Chem. Soc., vol. 103, pp. 5454-5459.
Palmer et al. (1994), "Synthesis of the Calophyllum coumarins," Tet. Letters, vol. 35, pp. 5363-5366.
Kashman et al. (1992), "The Calanolides, a Novel HIV-Inhibitory Class of Coumarin Derivatives from the Tropical Rainforest Tree, Calophyllum lanigerum," J. Med. Chem., vol. 35, pp. 2735-2743.
Games et al. (1972), "Identification of 4-Phenyl and 4-Alkycoumarins in Mammea Americana L., Mammea Africana G. Don and Calophyllum Inophyllum by Gas Chromatography-Mass Spectrometry," Tet. Letters, vol. 31, pp. 3187-3190.
Crombie et al. (1966), "Isolation and Structure of Mammea B/BA, B/BB, B/BC and C/BB: A Group of 4-m-Propyl- and 4-n-Amyl-Coumarin Extractives of Mammea Americana L.," Tet. Letters, vol. 2, pp. 151-156.
Cooper et al. (1994), GR15987 and Related Analogues as Highly Potent, Orally Active Non-Peptide Neurokinin NK.sub.2 Receptor Antagonists, Bioorganic & Med. Chem. Lett., vol. 4, pp. 1951-1956.
Hizi et al. (1993), "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 Nonnuceloside Inhibitors," Antimicrobial Agents and Chemotherapy, vol. 37, pp. 1037-1042.
Buckheit et al. (1995), "Comparative Anti-HIV Evaluation of Diverse HIV-1-Specific Reverse Transcriptase Inhibitor-Resistant Virus Isolates Demonstrates the Existence of Distinct Phenotypic Subgroups," Antiviral Research, vol. 26, pp. 117-132.
Buckheit et al. (1995), "Resistance to 1-[(2-Hydroxyethoxy)methyl]-6-(phenylthio)thymine Derivatives is Generated by Mutations at Multiple Sites in the HIV-1 Reverse Transcriptase," Virology, vol. 210, pp. 186-193.
Boyer et al. (1993), "Analysis of Nonnucleoside Drug-Resistant Variants of Human Immunodeficiency Virus Type 1 Reverse Transcriptase," J. Virology, vol. 67, pp. 2412-2420.
McKee et al. (1995), "The Pseudocalanolides: Structure Revision of Calanolides C and D," J. Natural Products, vol. 58, pp. 916-920.
Kucherenko et al. (1995), "Novel Approach for Synthesis of (.+-.)-Calanolide A and Its Anti-HIV Activity," Tet. Letters, vol. 36, pp. 5475-5478.
Gustafson et al. (1994), "Calanone, a Novel Coumarin From Calophyllum teysmannii," vol. 35, pp. 5821-5824.
Kashman et al. (1993), "The Calanolides, a Novel HIV-Inhibitory Class of Coumarin Derivatives from the Tropical Rainforest Tree, Calophyllum lanigerum," J. Med. Chem., vol. 36, pp. 1110.
Bader et al. (1991), "Oxathiin Carboxanilide, a Potent Inhibitor of Human Immunodeficiency Virus Reproduction," Proc. Natl. Acad. Sci. USA, vol. 88, pp. 6740-6744.
Borch et al. (1971), "The Cyanohydridoborate Anion as a Selective Reducing Agent," J. Amer. Chem. Soc., vol. 93, pp. 2897-2904.
Buckheit et al. (1994), "Cell-Based and Biochemical Analysis of the Anti-HIV Activity of Combination of 3'-Azido-3'-Deoxythymidine and Analogues of TIBO," Antiviral Chemistry & Chemotherapy, vol. 5(1), pp. 35-42.
Castro, B.R. (1983), "Replacement of Alcoholoc Hydroxyl Groups by Halogens and Other Nucleophiles via Oxyphosphonium Intermediates," Org. React., vol. 29, pp. 1-162.
Cooper et al. (1994), GR15987 and Related Analogues as Highly Potent, Orally Active Non-Peptide Neurokinin NK.sub.2 Receptor Antagonists, Bioorganic & Med. Chem. Lett., vol. 4, pp. 1951-1956.
Feuer et al. (1965), "The Reduction of Oximes with Diborane. A New Synthesis of N-Monosubstituted Hydroxylamines," J. Org. Chem., vol. 30, pp. 2877-2880.
Feuer and Braunstein (1969), "The Reduction of Oximes, Oxime Ethers, and Oxime Esters with Diborane. A Novel Synthesis of Amines," J. Org. Chem.vol. 34, pp. 1817-1821.
Hudlicky, M. (1988), "Fluorination with Diethylaminosulfur Trifluoride and Related Aminofluorosulfuranes," Org. React., vol. 35, pp. 513-637.
Hughes, D.L. (1992), "The Mitsunobu Reaction," Organic Reaction, vol. 42, pp. 335-656.
Kukla et al. (1991), "Synthesis and Anti-HIV-1 Activity of 4,5,6,7-Tetrahydro-5-methylimidazo[4,5,1-jk] [1,4]benzodiazepin-2 (1H)-one (TIBO) Derivatives," J. Medicinal Chemistry, vol. 34, pp. 746-751.
Lin et al. (1994), "Synthesis and Biological Evaluation of 2',3'-Dideoxy-L-pyrimidine Nucleosides as Potential Antiviral Agents Against Human Immunodeficiency Virus (HIV) and Hepatitis B Virus (HBV)," J. Med. Chem., vol. 37, pp. 798-803.
Massa et al. (1995), "Synthesis and Antiviral Activity of New 3,4-dihydro-2-alkoxy-6-benzyl-4-oxopyrimidines (DABOs), Specific Inhibitors of Human Immunodeficiency Virus Type 1," Antiviral Chemistry and Chemotherapy, vol. 6, pp. 1-8.
Mayaux et al. (1994), "Triterpene Derivatives that Block Entry of Human Immunodeficiency Virus Type 1 Into Cells," Proc. Natl. Acad. Sci. USA, vol. 91, pp. 3564-3568.
McGuigan et al. (1994), "Synthesis and Anti-HIV Activity of Some Novel Diaryl Phosphate Derivatives of AZT," Antiviral Research, vol. 24, pp. 69-77.
McMahon et al. (1993), "Diarylsulfones, a New Chemical Class of Necleoside Antiviral Inhibitors of Human Immunodeficiency Virus Type 1 Reverse Transcriptase," Antimicrobial Agents and Chemotherapy, vol. 37, pp. 754-760.
Meier et al. (1992), "O-Alkyl-5',5'-dinucleoside Phosphates as Prodrugs of 3'-Azidothymidine and Cordycepin," J. Org. Chem., vol. 57, pp. 7300-7308.
Merluzzi et al. (1990), "Inhibition of HIV-1 Replication by a Nucleoside Reverse Transcriptase Inhibitor," Science, vol. 250, pp. 1411-1413.
Mitsunobu, O. (1981), "The Use of Diethyl Azodicarboxylate and Triphenylphosphine in Synthesis and Transformation of Natural Products," Synthesis, pp. 1-28.
Miyasaka et al. (1989), "A Novel Lead for Specific Anti-HIV-1 Agents: 1-[(2-Hydroxyethoxy)methyl]-6-(phenylthio)-thymine," J. Medicinal Chemistry, vol. 32, pp. 2507-2509.
Nielsen and Houlihan (1986), "The Aldol Condensation," Org. React., vol. 16, pp. 1-438.
Pauwels et al. (1990), "Potent and Selective Inhibition of HIV-1 Replication In Vitro by a Novel Series of TIBO Derivatives," Nature, vol. 343, pp. 470-474.
Pauwels et al. (1988), "Rapid and Automated Tetrazolium-Based Colorimetric Assay for the Detection of Anti-HIV Compounds," J. Virological Methoods, vol. 309-321.
Sergheraert et al. (1993), Synthesis and Anti-HIV Evaluation of D4T and D4T 5'-Monophosphate Prodrugs, J. Medicinal Chemistry, vol. 36, pp. 826, 830.
Wasserman et al. (1989), "The Chemistry of Vicinal Tricarbonyls, Use of Vinyl Tricarbonyl Esters in the Formation of 3-Hydroxyupyrrole-2-Carboxylates," Tet. Letters, vol. 30, pp. 1721-1724.
Bandara et al. (1986), "Two Chemically Distinct Groups of Calophyllum Species From Sri Lanka," Phytochemistry, vol. 25, pp. 425-428.
Boyd, M., "AIDS: Etiology, Diagnosis Treatment and Prevention," Chapter 18, 2nd Ed., J.B. Lippincott Co., Devita et al., ed., pp. 305-317.
Chaturvedi et al. (1974), "Anticonvulsant and Antinflammatory Activity of Natural Plant Coumarins and Triterpenoids," Res. Communications in Chemical Pathology and Pharmacology, vol. 9, pp. 11-22.
Craig et al. (1991), "Antiviral Properties of Ro 31-8959, An Inhibitor of Human Immunodeficiency Virus (HIV) Proteinase," Antiviral Research, vol. 16, pp. 295-305.
Dahanayake et al. (1974), "Chemical Investigation of Ceylonese Plants. Part VII. Extractives of Calophyllum thwaitesii Planch and Triana and Calophyllum walkeri Wight (Guttiferae)," J.C.S. Perkin I, pp. 2510-2514.
Dharmaratne et al

LandOfFree

Say what you really think

Search LandOfFree.com for the USA inventors and patents. Rate them and share your experience with other people.

Rating

Method for the preparation of (+)-calanolide A and analogues the does not yet have a rating. At this time, there are no reviews or comments for this patent.

If you have personal experience with Method for the preparation of (+)-calanolide A and analogues the, we encourage you to share that experience with our LandOfFree.com community. Your opinion is very important and Method for the preparation of (+)-calanolide A and analogues the will most certainly appreciate the feedback.

Rate now

     

Profile ID: LFUS-PAI-O-2137431

  Search
All data on this website is collected from public sources. Our data reflects the most accurate information available at the time of publication.