83507-89-5Relevant academic research and scientific papers
Synthesis of N-butyloxycarbonylalanyl-1,4-dioxa-7-azaspiro[4,4]nonane-8(s)-carboxylic acid ethyl ester
Slavinskaya,Chipens,Sile,Korchagova,Katkevich,Grigor'eva,Lukevits
, p. 568 - 570 (1996)
A four-step method has been developed for the synthesis of N-butyloxycarbonylalanyl-1,4-dioxa-7-azaspiro-[4,4]nonane-8(S)-carboxylic acid ethyl ester through the formation of N-benzyloxycarbonyl-1,4-dioxa-7-azaspiro[4,4]nonane-8(S)-carboxylic acid ethyl e
Thrombin inhibitors from the freshwater cyanobacterium Anabaena compacta
Anas, Andrea Roxanne J.,Kisugi, Takaya,Umezawa, Taiki,Matsuda, Fuyuhiko,Okino, Tatsufumi,Campitelli, Marc R.,Quinn, Ronald J.
, p. 1546 - 1552,7 (2012/12/12)
Bioassay-guided investigation of the cyanobacterium Anabaena compacta extracts afforded spumigin J (1) and the known thrombin inhibitor spumigin A (2). The absolute configuration of 1 was analyzed by advanced Marfey's methodology. Compounds 1 and 2 inhibi
Thrombin inhibitors from the freshwater cyanobacterium Anabaena compacta
Anas, Andrea Roxanne J.,Kisugi, Takaya,Umezawa, Taiki,Matsuda, Fuyuhiko,Campitelli, Marc R.,Quinn, Ronald J.,Okino, Tatsufumi
, p. 1546 - 1552 (2013/01/15)
Bioassay-guided investigation of the cyanobacterium Anabaena compacta extracts afforded spumigin J (1) and the known thrombin inhibitor spumigin A (2). The absolute configuration of 1 was analyzed by advanced Marfey's methodology. Compounds 1 and 2 inhibi
Concise, stereoselective route to the four diastereoisomers of 4-methylproline
Murphy, Annabel C.,Mitova, Maya I.,Blunt, John W.,Munro, Murray H.G.
experimental part, p. 806 - 809 (2009/04/07)
The full stereochemical characterization of 4-methylproline, a rare amino acid found in a number of peptidic secondary metabolites, has often been hindered by long reaction sequences or low stereoselectivity in the synthesis leading to reference samples. The preparation of the four diastereoisomers of 4-methylproline by a concise and stereoselective route is presented and features a six-step route with late-stage stereodivergence, good stereoselectivity for both cis- and trans-series (75% and 88% de, respectively), and good overall yields (cumulative yields of 30-40%). Additional data on the Marfey's derivatives of the stereoisomers are also presented.
Angiotensin Converting Enzyme Inhibitors: Spirapril and Related Compounds
Smith, Elizabeth M.,Swiss, Gerald F.,Neustadt, Bernard R.,McNamara, Paul,Gold, Elijah H.,et al.
, p. 1600 - 1606 (2007/10/02)
The synthesis of spirapril (5), spiraprilat (25), their RSS stereoisomers, and their glycyl (18b) and lysyl (36, 37) analogues is described.These compounds were evaluated in vivo for inhibition of angiotensin converting enzyme (ACE), and selected compounds were evaluated for in vitro ACE inhibition (spirapril ID50 16 μg/kg; spiraprilat IC50 0.8 nM, ID50 8 μg/kg).In anesthetized rats, iv, esters 5 and 36 are more potent than enalapril, and diacids 25 and 37 are more potent than enalaprilat in vitro.In the conscious rats, orally, 5 and enalapril (2) showed potent and sustained activity at doses of 0.03-1 and 0.1-1 mg/kg, respectively.From this work, spirapril was selected for clinical evaluation as an antihypertensive agent.
