1000596-44-0Relevant academic research and scientific papers
Anti-AIDS agents 81. design, synthesis, and structure-activity relationship study of betulinic acid and moronic acid derivatives as potent HIV maturation inhibitors
Qian, Keduo,Kuo, Reen-Yun,Chen, Chin-Ho,Huang, Li,Morris-Natschke, Susan L.,Lee, Kuo-Hsiung
experimental part, p. 3133 - 3141 (2010/09/18)
In our continuing study of triterpene derivatives as potent anti-HIV agents, different C-3 conformationally restricted betulinic acid (BA, 1) derivatives were designed and synthesized in order to explore the conformational space of the C-3 pharmacophore. 3-O-Monomethylsuccinyl-betulinic acid (MSB) analogues were also designed to better understand the contribution of the C-3′ dimethyl group of bevirimat (2), the first-in-class HIV maturation inhibitor, which is currently in phase IIb clinical trials. In addition, another triterpene skeleton, moronic acid (MA, 3), was also employed to study the influence of the backbone and the C-3 modification toward the anti-HIV activity of this compound class. This study enabled us to better understand the structure-activity relationships (SAR) of triterpene-derived anti-HIV agents and led to the design and synthesis of compound 12 (EC50: 0.0006 μM), which displayed slightly better activity than 2 as a HIV-1 maturation inhibitor.
Anti-AIDS agents 73: Structure-activity relationship study and asymmetric synthesis of 3-O-monomethylsuccinyl-betulinic acid derivatives
Qian, Keduo,Nakagawa-Goto, Kyoko,Yu, Donglei,Morris-Natschke, Susan L.,Nitz, Theodore J.,Kilgore, Nicole,Allaway, Graham P.,Lee, Kuo-Hsiung
, p. 6553 - 6557 (2008/03/18)
3-O-3′(or 2′)-Methylsuccinyl-betulinic acid (MSB) derivatives were separated by using recycle HPLC. The structures of four isomers were assigned by NMR and asymmetric synthesis. 3-O-3′S-Methylsuccinyl-betulinic acid (3′S-MSB, 4) exhibited potent anti-HIV
Total Synthesis of (-)-Stemoamide
Williams, David R.,Reddy, Jayachandra P.,Amato, George S.
, p. 6417 - 6420 (2007/10/02)
An enantiocontrolled total synthesis of the tricyclic alkaloid, stemoamide (2), is reported. Key Words: Asymmetric aldol; chiral butyrolactone synthesis; selective 1,3-acyclic diol formation.
Studies directed toward the total synthesis of tetronolide 1. An enantioselective synthesis of the octahydronaphthalene unit
Boeckman Jr., Robert K.,Barta, Thomas E.,Nelson, Scott G.
, p. 4091 - 4094 (2007/10/02)
An efficient enantioselective route to the octahydronaphthalene unit present in tetronolide (1), the stereochemically complex aglycone common to the tetrocarcins, a novel group of antitumor substances, is described. The sequence employs the intramolecular
