80629-36-3

Usage

Uses

Used in Pharmaceutical Industry:
(R)-1-(3-BroMo-2-Methyl-1-oxopropyl)-L-proline is used as a key intermediate in the synthetic preparation of Captopril (C175750), an orally active angiotensin-converting enzyme (ACE) inhibitor. This application is crucial for the development of medications that help regulate blood pressure and treat hypertension, as well as manage heart failure and certain kidney disorders.
As an intermediate in the synthesis of Captopril, (R)-1-(3-BroMo-2-Methyl-1-oxopropyl)-L-proline contributes to the production of a drug that has a significant impact on the treatment of cardiovascular diseases. Its role in the pharmaceutical industry highlights the importance of chiral compounds in the development of effective and targeted medications.

Upstream product

• 71271-28-8 3-bromo-2-methylpropanoyl chloride 
• 147-85-3 L-proline 

Downstream Products

• 1275614-34-0 C₁₇H₂₃NO₄Se 
• 1275614-31-7 C₁₇H₂₃NO₄Se 

Relevant academic research and scientific papers

Synthesis, characterization and antioxidant activity of angiotensin converting enzyme inhibitors

Angiotensin converting enzyme (ACE) catalyzes the conversion of angiotensin I (Ang I) to angiotensin II (Ang II). ACE also cleaves the terminal dipeptide of vasodilating hormone bradykinin (a nonapeptide) to inactivate this hormone. Therefore, inhibition of ACE is generally used as one of the methods for the treatment of hypertension. 'Oxidative stress' is another disease state caused by an imbalance in the production of oxidants and antioxidants. A number of studies suggest that hypertension and oxidative stress are interdependent. Therefore, ACE inhibitors having antioxidant property are considered beneficial for the treatment of hypertension. As selenium compounds are known to exhibit better antioxidant behavior than their sulfur analogues, we have synthesized a number of selenium analogues of captopril, an ACE inhibitor used as an antihypertensive drug. The selenium analogues of captopril not only inhibit ACE activity but also effectively scavenge peroxynitrite, a strong oxidant found in vivo. The Royal Society of Chemistry 2011.

An improved synthesis of captopril

An improved synthesis of captopril using methacrylic acid as the starting material is described. Treatment of methacrylic acid (I) with a hydrogen halide gave the 3-halogeno-2-methylpropanoic acids II and III, which were treated with thionyl chloride to yield the corresponding 3-halogeno-2-methylpropanoyl chlorides IV and V. Treatment of IV or V with L-proline yielded the N-(R,S-3-halogeno-2-methylpropanoyl)-L-prolines VI and VII, which were separated into optically pure R- and S-diastereoisomers using dicyclohexylamine. Treatment of halides of VI or VII with methanolic ammonium hydrosulfide gave captopril in 28% yield.

Selenium containing derivatives of proline and pipecolic acid

New selenium containing derivatives of proline and pipecolic acid which have the general formula STR1 are useful as hypotensive agents.