518047-98-8Relevant articles and documents
A Scalable Synthesis of 2-(1,2,4-Oxadiazol-3-yl)propan-2-amine Hydrobromide Using a Process Safety-Driven Protecting Group Strategy
Likhite, Nachiket,Lakshminarasimhan, Thirumalai,Rao, Mallem H. V. Ramana,Shekarappa, Vijaykumar,Sidar, Somprabha,Subramanian, Varadharajan,Fraunhoffer, Kenneth J.,Leung, Simon,Vaidyanathan, Rajappa
, p. 1328 - 1335 (2016/07/23)
A safe and scalable synthesis of 2-(1,2,4-oxadiazol-3-yl)propan-2-amine hydrobromide is described. A process safety-driven synthetic strategy was employed for the selection of thermally stable compounds en route to the target 1,2,4-oxadiazole. Application
Structural modifications of 5,6-dihydroxypyrimidines with anti-HIV activity
Guo, Di-Liang,Zhang, Xing-Jie,Wang, Rui-Rui,Zhou, Yu,Li, Zeng,Xu, Jin-Yi,Chen, Kai-Xian,Zheng, Yong-Tang,Liu, Hong
supporting information, p. 7114 - 7118 (2013/01/15)
A series of 5,6-dihydroxypyrimidine analogs were synthesized and evaluated for their anti-HIV activity in vitro. Among all of the analogs, several compounds exhibited significant anti-HIV activity, especially 1b and 1e, which showed the most potent anti-HIV activity with EC50 values of 0.14 and 0.15 μM, and TI (therapeutic index) values of >300 and >900, respectively. Further docking studies revealed that the representative compounds 1e and 3a could meet the HIV-1 integrase inhibition minimal requirements of a chelating domain (two metal ions) and an aromatic domain (π-π stacking interactions).
Development of a second-generation, highly efficient manufacturing route for the HIV integrase inhibitor raltegravir potassium
Humphrey, Guy R.,Pye, Philip J.,Zhong, Yong-Li,Angelaud, Remy,Belyk, Kevin M.,Maligres, Peter E.,Miller, Ross A.,Reamer, Robert A.,Askin, David,Mancheno, Danny E.,Weissman, Steven A.
experimental part, p. 73 - 83 (2011/09/16)
A manufacturing route for the synthesis of raltegravir potassium 1 was developed via a thermal rearrangement of amidoxime DMAD adducts 6 to construct the key, highly functionalized hydroxypyrimidinone core 7. Utilizing this route 1 was prepared in nine linear chemical steps with 22% overall yield. A second-generation synthesis was subsequently developed that solved the key chemical, productivity, and environmental impact issues of the initial synthesis. Highlights of the new synthesis include a highly selective methylation, 3-4-fold higher productivity, and a 65% reduction of combined organic and aqueous waste produced. The efficient second-generation manufacturing route provides raltegravir potassium 1 in 35% overall yield.