72679-02-8Relevant articles and documents
Method for preparing S-(-)-Benzoylthio-2-methylpropanoic acid compound
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Paragraph 0020; 0021, (2019/04/30)
The invention discloses a method for preparing a S-(-)-Benzoylthio-2-methylpropanoic acid compound. S-(-)-3-acetylthio-2-methylpropionic acid as a raw material shown in the formula II is hydrolyzed ina reacting solvent to obtain S-(-)-3-mercapto-2-methylpropionic acid shown in hte formula III, and the S-(-)-3-mercapto-2-methylpropionic acid and benzoyl chloride are subjected to condensation to obtain the S-(-)-Benzoylthio-2-methylpropanoic acid shown in the formula I. The preparation method is easy in operation, the raw materials and accessory materials are low in cost and easy to obtain, thereaction conditions are mild, the yield is high, and the quality is high. (The formula is shown in the description.).
Studies on angiotensin-converting enzyme inhibitors. I. Syntheses and angiotensin-converting enzyme inhibitory activity of 2-(3-merecaptopropionyl)-1,2,3,4-tetrahydroisoquinoline-3-carboxylic acid derivatives
Hayashi,Ozaki,Nunami,Uchida,Kato,Kinashi,Yoneda
, p. 570 - 576 (2007/10/02)
(3S)-2-[(2S)-mercapto-2-methylpropionyl]-1,2,3,4-tetrahydroisoquinoline-3-carboxylic acid [(3S), (2S)-6a] was prepared by the reaction of (3S)-1,2,3,4-tetrahydreoisoquinoline-3-carboxylic acid test-butyl ester [(3S)-2a) or benzyl ester [(3S)-2b] with 3-benzoylthio-2-methylpropionyl chloride (3a), followed by fractional crystallization and removal of the protective group. The absolute configuration of (3S), (2S)-6a was confirmed by X-ray diffraction analysis of the thiazepinol[4,3-b]isoquinoline compound (7) derived from 6a. Resolution of 3-benzoylthio-2-methylpropionic acid (8) was completed by using optically active phenylalanine amide as a resolving agent. The other optical isomers of (3S),(2S)-6a were prepared by the reaction of (3S)- or (3R)-2b with optically active 3a. The in vitro ACE inhibitory activity of each isomer of 6a was evaluated. Among them, (3S),(2S)-6a was found to be the most potent inhibitor with an IC50 value of 8.6X10-9M. Compound (3S),(2S)-6a induced a dose-dependent inhibition of the pressor response to angiotensin 1 after oral administration to normotensive anesthetized rats. Moreover, (3S),(2S)-6a markedly reduced the systolic blood pressure in renal hypertensive rats (RHR) and spontaneously hypertensive rats (SHR). The in vivo ACE inhibitory activity and the hypotensive effects of (3S),(2S)-6a were comparable to those of captopril.
Synthesis of captopril starting from an optically active β-hydroxy acid
Shimazaki,Hasegawa,Kan,et al.
, p. 3139 - 3146 (2007/10/02)
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