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Mechanochemical enzymatic synthesis of 1,4‐dihydropyridine calcium antagonists and derivatives
Journal of chemical technology and biotechnology (1986), 2019-08, Vol.94 (8), p.2555-2560
Jiang, Ling
Ye, Li‐dan
Gu, Jia‐li
Su, Wei‐ke
Ye, Wen‐ting
2019
Details
Autor(en) / Beteiligte
Jiang, Ling
Ye, Li‐dan
Gu, Jia‐li
Su, Wei‐ke
Ye, Wen‐ting
Titel
Mechanochemical enzymatic synthesis of 1,4‐dihydropyridine calcium antagonists and derivatives
Ist Teil von
Journal of chemical technology and biotechnology (1986), 2019-08, Vol.94 (8), p.2555-2560
Ort / Verlag
Chichester, UK: John Wiley & Sons, Ltd
Erscheinungsjahr
2019
Link zum Volltext
Quelle
Wiley-Blackwell Journals
Beschreibungen/Notizen
BACKGROUND Enzyme promiscuity has attracted significant attention from chemists and biochemists in recent years. However, long reaction time and use of toxic organic solvents limit its applications for industrial processes. 1,4‐Dihydropyridine (1,4‐DHP) calcium antagonists are recommended for the first line treatment of hypertension. Although some chemical protocols for the preparation of 1,4‐DHP calcium antagonists have been developed, enzymatic synthesis of these compounds still remains uncovered. RESULTS Solvent‐free quick synthesis of 1,4‐DHP calcium antagonists felodipine, nitrendipine, nifedipine and nemadipine B and their derivatives was achieved by Lipozyme® RM IM (triacylglycerol acylhydrolase, EC3.1.1.3)‐catalyzed multicomponent reactions of aromatic aldehyde, alkyl acetoacetate and alkyl 3‐aminocrotonate under ball‐milling conditions. The products were obtained in moderate yields (up to 86.8%) and the influence of reaction conditions including catalyst loading, grinding auxiliary and grinding frequency was investigated. CONCLUSION The protocol successfully overcame some longstanding problems in the field of enzymatic promiscuity research, such as long reaction time and use of harmful organic solvents, and demonstrated the potential application value of promiscuous enzyme‐catalyzed reactions under ball‐milling conditions for pharmaceutical synthesis. © 2019 Society of Chemical Industry
Sprache
Englisch
Identifikatoren
ISSN: 0268-2575
eISSN: 1097-4660
DOI: 10.1002/jctb.6051
Titel-ID: cdi_proquest_journals_2333898672
Format
–
Schlagworte
1,4‐dihydropyridine calcium antagonists
,
Aldehydes
,
Antagonists
,
ball milling
,
Calcium
,
Calcium antagonists
,
Calcium compounds
,
Catalysts
,
Chemical reactions
,
Chemical synthesis
,
Chemists
,
Comminution
,
Derivatives
,
Dihydropyridine
,
enzymatic promiscuity
,
Enzymatic synthesis
,
Enzymes
,
Felodipine
,
Grinding
,
Hypertension
,
Lipozyme® RM IM
,
multicomponent reactions
,
Nifedipine
,
Organic chemistry
,
Organic solvents
,
Reaction time
,
Solvents
,
Triglycerides
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