Ammonium Azide

Obenland, C. O.; Mangold, D. J.; Marino, M. P.; Musgrave, Thea; Keller, R. N.

doi:10.1002/9780470132395.ch15

Cited by 7 publications

(2 citation statements)

References 3 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…Upon concentration of the water, crystallization occurred. Filtration and air-drying gave 3.2 g (77%) of (4R,5R)-2,2-dimethyl-4,5-bis(5-tetrazolyl)-1,3-dioxolane which upon recrystallization from water gave white needles: mp 215-216°C; (1R,2R)-Dihydroxy-1-carbamoyl-2-(5-tetrazolyl)ethane (37). To 40 mL of DMF was added the cyanoamide dioxolane 36 (1.95 g, 11.46 mmol), ammonium sulfate (1.52 g, 11.46 mmol), and sodium azide (1.5 g, 22.92 mmol).…”

Section: Methodsmentioning

confidence: 99%

“…The known 35 acetonide 32 of the diamide of L-tartaric acid was dehydrated to give primarily the dicyano acetonide 33 or the cyanoamide acetonide 36 depending on the equivalents of tosyl chloride used. 36 Reaction of 33 with ammonium azide 37 gave the bistetrazole acetonide, which was hydrolyzed to the bis-tetrazole 34 with HCl. Following the same procedures, 36 gave the amide-tetrazole 37.…”

Section: Synthesismentioning

confidence: 99%

See 1 more Smart Citation

Design, Synthesis, and Biological Evaluation of Novel Hybrid Dicaffeoyltartaric/Diketo Acid and Tetrazole-Substitutedl-Chicoric Acid Analogue Inhibitors of Human Immunodeficiency Virus Type 1 Integrase

Crosby¹,

Lei

Gibbs

et al. 2010

J. Med. Chem.

View full text Add to dashboard Cite

Fourteen analogues of the anti-HIV-1 integrase (IN) inhibitor L-chicoric acid (L-CA) were prepared. Their IC(50) values for 3'-end processing and strand transfer against recombinant HIV-1 IN were determined in vitro, and their cell toxicities and EC(50) against HIV-1 were measured in cells (ex vivo). Compounds 1-6 are catechol/β-diketoacid hybrids, the majority of which exhibit submicromolar potency against 3'-end processing and strand transfer, though only with modest antiviral activities. Compounds 7-10 are L-CA/p-fluorobenzylpyrroloyl hybrids, several of which were more potent against strand transfer than 3'-end processing, a phenomenon previously attributed to the β-diketo acid pharmacophore. Compounds 11-14 are tetrazole bioisosteres of L-CA and its analogues, whose in vitro potencies were comparable to L-CA but with enhanced antiviral potency. The trihydroxyphenyl analogue 14 was 30-fold more potent than L-CA at relatively nontoxic concentrations. These data indicate that L-CA analogues are attractive candidates for development into clinically relevant inhibitors of HIV-1 IN.

show abstract

Section: Methodsmentioning

confidence: 99%