183904-54-3

Basic information

• Product Name: Aids033397
• Synonyms: (-)-(trans)-2H,6H,12H-Benzo[1,2-B:3,4-B':5,6-B'']tripyran-2,12-dione, 10,11-dihydro-6,6,10,11-tetramethyl-4-propyl-, (10S,11S)-;(-)-12-Oxocalanolide b;2H,6H,12H-Benzo[1,2-B:3,4-B':5,6-B'']tripyran-2,12-dione, 10,11-dihydro-6,6,10,11-tetramethyl-4-propyl-, (10S-trans)-;Aids033397;Aids-033397
• CAS NO: 183904-54-3
• Molecular Formula: C22H24O5
• Molecular Weight: 368.42296
• Mol File: 183904-54-3.mol
• Article Data: 4

Chemical Properties

• Boiling Point: 546.7°Cat760mmHg
• Flash Point: 298.4°C
• Appearance: /
• Density: 1.176g/cm³
• CAS DataBase Reference: Aids033397(CAS DataBase Reference)
• NIST Chemistry Reference: Aids033397(183904-54-3)
• EPA Substance Registry System: Aids033397(183904-54-3)

Safety Data

• Hazardous Substances Data: 183904-54-3(Hazardous Substances Data)

Upstream product

• 161753-49-7 (+/-)-12-oxocalanolide A 
• 909-14-8 (-)-calanolide B 
• 166983-61-5 HI-D₁₂ 
• 334881-61-7 (8R,9S)-8,9-dihydro-8,9-dimethyl-5-methoxy-4-propyl-2H,10H-benzo[1,2-b;5,6-b']dipyran-2,10-dione 
• 107-86-8 3,3-dimethyl acrylaldehyde 
• 685844-44-4 5-hydroxy-8,9-dimethyl-4-propyl-8,9-dihydro-pyrano[2,3-f]chromene-2,10-dione 
• 263351-94-6 (10R,11S)-10,11-dihydro-4-propyl-6,6,10,11-tetramethyl-2H,6H,12H-benzo[1,2-b;3,4-b';5,6-b'']tripyran-2,12-dione 
• 185339-28-0 5-Hydroxy-6-((2R,3R)-3-hydroxy-2-methyl-butyryl)-2,2-dimethyl-10-propyl-2H-pyrano[2,3-f]chromen-8-one 
• 185339-26-8 5-Hydroxy-6-((2R,3S)-3-hydroxy-2-methyl-butyryl)-2,2-dimethyl-10-propyl-2H-pyrano[2,3-f]chromen-8-one 

Downstream Products

• 909-13-7 7,8-dihydro-(-)-calanolide B 

Relevant articles and documents

Concise Synthesis of Anti-HIV-1 Active (+)-Inophyllum B and (+)-Calanolide A by Application of (-)-Quinine-Catalyzed Intramolecular Oxo-Michael Addition

(-)-Quinine-catalyzed intramolecular oxo-Michael addition (IMA) of 7-hydroxy-5-methoxy-8-tigloylcoumarins was developed for the enantioselective construction of 2,3-dimethyl-4-chromanone systems in the context of the asymmetric synthesis of anti-HIV-1 act

Structure-activity modifications of the HIV-1 inhibitors (+)-calanolide A and (-)-calanolide B

The Δ7,8 olefinic linkages within (+)-calanolide A (1) and (-)- calanolide B (2) were catalytically reduced to determine impact on the anti- HIV activity of the parent compounds. In addition, a series of structure modifications of the C-12 hydroxyl group in (-)-calanolide B was made to investigate the importance of that substituent to the HIV-1 inhibitory activity of these coumarins. A total of 14 analogs were isolated or prepared and compared to (+)-calanolide A and (-)-calanolide B in the NCI primary anti-HIV assay. While none of the compounds showed activity superior to the two unmodified leads, some structure-activity requirements were apparent from the relative anti-HIV potencies of the various analogs.