title: Novel lavendamycin analogues as potent HIV-reverse transcriptase inhibitors: synthesis and evaluation of anti-reverse transcriptase activity of amide and ester analogues of lavendamycin.
abstract: Novel lavendamycins including two water soluble derivatives were synthesized via short and efficient methods. Pictet-Spengler condensation of 7-N-acylamino-2-formylquinoline-5,8-diones with tryptophans produced lavendamycin esters or amides 11-17. Lavendamycins 18-21 were obtained, respectively, by further transformations of 13-15 and 17. Several lavendamycins were found to be potent HIV reverse transcriptase inhibitors with very low toxicity in vitro and in vivo. Several compounds also acted either additively or synergistically to inhibit enzyme activity together with AZT-triphosphate.
authors.affiliation: Chemistry and Biology Departments, Ball State University, Muncie, Indiana 47306-0440, USA.
authors.forename: Mohammad
authors.initials: M
authors.lastname: Behforouz
authors.forename: Wen
authors.initials: W
authors.lastname: Cai
authors.forename: Mark G
authors.initials: MG
authors.lastname: Stocksdale
authors.forename: Jennifer S
authors.initials: JS
authors.lastname: Lucas
authors.forename: Joo Yong
authors.initials: JY
authors.lastname: Jung
authors.forename: Daniel
authors.initials: D
authors.lastname: Briere
authors.forename: Aiqin
authors.initials: A
authors.lastname: Wang
authors.forename: Kevin S
authors.initials: KS
authors.lastname: Katen
authors.forename: Nancy C
authors.initials: NC
authors.lastname: Behforouz
mesh_terms: D000577:Amides / Q000138:chemical synthesis* / Q000494:pharmacology / Q000633:toxicity; D000818:Animals; D002478:Cells, Cultured; D054306:Dideoxynucleotides; D004357:Drug Synergism; D004952:Esters / Q000138:chemical synthesis / Q000494:pharmacology / Q000633:toxicity; D054303:HIV Reverse Transcriptase / Q000037:antagonists & inhibitors*; D006801:Humans; D051379:Mice; D018894:Reverse Transcriptase Inhibitors / Q000138:chemical synthesis* / Q000494:pharmacology / Q000633:toxicity; D013308:Streptonigrin / Q000031:analogs & derivatives* / Q000138:chemical synthesis* / Q000494:pharmacology / Q000633:toxicity; D013329:Structure-Activity Relationship; D013942:Thymine Nucleotides / Q000494:pharmacology; D015215:Zidovudine / Q000031:analogs & derivatives* / Q000494:pharmacology
chemical_list: D000577:Amides; D054306:Dideoxynucleotides; D004952:Esters; D018894:Reverse Transcriptase Inhibitors; D013942:Thymine Nucleotides; D013308:Streptonigrin; D015215:Zidovudine; C052873:zidovudine triphosphate; C034566:lavendamycin; D054303:HIV Reverse Transcriptase