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A New Class of Potential Chloroquine-Resistance Reversal Agents for Plasmodia: Syntheses and Biological Evaluation of 1-(3‘-Diethylaminopropyl)-3-(substituted phenylmethylene)pyrrolidines

1-(3‘-Diethylaminopropyl)-3-(substituted phenylmethylene)pyrrolidines were synthesized and evaluated for CQ-resistant reversal activity. In general the compounds of the series elicit better biological response than their phenylmethyl analogues. The most active compound 4b has been evaluated in vivo...

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Published in:	Journal of medicinal chemistry 2000-09, Vol.43 (18), p.3428-3433
Main Authors:	Batra, Sanjay, Srivastava, Pratima, Roy, Kamal, Pandey, V. C, Bhaduri, A. P
Format:	Article
Language:	English
Subjects:	Animals Antibiotics. Antiinfectious agents. Antiparasitic agents Antimalarials - chemical synthesis Antimalarials - chemistry Antimalarials - pharmacology Antiparasitic agents Biological and medical sciences Chloroquine - pharmacology Drug Resistance Drug Resistance, Multiple Heme - antagonists & inhibitors Heme - metabolism Heme Oxygenase (Decyclizing) - antagonists & inhibitors Heme Oxygenase (Decyclizing) - metabolism Hemeproteins - antagonists & inhibitors Hemeproteins - metabolism Medical sciences Mice Pharmacology. Drug treatments Plasmodium - drug effects Plasmodium - metabolism Pyrrolidines - chemical synthesis Pyrrolidines - chemistry Pyrrolidines - pharmacology Structure-Activity Relationship
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creator	Batra, Sanjay Srivastava, Pratima Roy, Kamal Pandey, V. C Bhaduri, A. P
description	1-(3‘-Diethylaminopropyl)-3-(substituted phenylmethylene)pyrrolidines were synthesized and evaluated for CQ-resistant reversal activity. In general the compounds of the series elicit better biological response than their phenylmethyl analogues. The most active compound 4b has been evaluated in vivo in detail, and the results are presented. The possible mode of action of the compounds of this series is by inhibition of the enzyme heme oxygenase, thereby increasing the levels of heme and hemozoin, which are lethal to the parasite.
doi_str_mv	10.1021/jm000083u
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The possible mode of action of the compounds of this series is by inhibition of the enzyme heme oxygenase, thereby increasing the levels of heme and hemozoin, which are lethal to the parasite.</description><identifier>ISSN: 0022-2623</identifier><identifier>EISSN: 1520-4804</identifier><identifier>DOI: 10.1021/jm000083u</identifier><identifier>PMID: 10978190</identifier><identifier>CODEN: JMCMAR</identifier><language>eng</language><publisher>Washington, DC: American Chemical Society</publisher><subject>Animals ; Antibiotics. Antiinfectious agents. 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C</creatorcontrib><creatorcontrib>Bhaduri, A. P</creatorcontrib><title>A New Class of Potential Chloroquine-Resistance Reversal Agents for Plasmodia: Syntheses and Biological Evaluation of 1-(3‘-Diethylaminopropyl)-3-(substituted phenylmethylene)pyrrolidines</title><title>Journal of medicinal chemistry</title><addtitle>J. Med. Chem</addtitle><description>1-(3‘-Diethylaminopropyl)-3-(substituted phenylmethylene)pyrrolidines were synthesized and evaluated for CQ-resistant reversal activity. In general the compounds of the series elicit better biological response than their phenylmethyl analogues. The most active compound 4b has been evaluated in vivo in detail, and the results are presented. The possible mode of action of the compounds of this series is by inhibition of the enzyme heme oxygenase, thereby increasing the levels of heme and hemozoin, which are lethal to the parasite.</description><subject>Animals</subject><subject>Antibiotics. Antiinfectious agents. Antiparasitic agents</subject><subject>Antimalarials - chemical synthesis</subject><subject>Antimalarials - chemistry</subject><subject>Antimalarials - pharmacology</subject><subject>Antiparasitic agents</subject><subject>Biological and medical sciences</subject><subject>Chloroquine - pharmacology</subject><subject>Drug Resistance</subject><subject>Drug Resistance, Multiple</subject><subject>Heme - antagonists & inhibitors</subject><subject>Heme - metabolism</subject><subject>Heme Oxygenase (Decyclizing) - antagonists & inhibitors</subject><subject>Heme Oxygenase (Decyclizing) - metabolism</subject><subject>Hemeproteins - antagonists & inhibitors</subject><subject>Hemeproteins - metabolism</subject><subject>Medical sciences</subject><subject>Mice</subject><subject>Pharmacology. Drug treatments</subject><subject>Plasmodium - drug effects</subject><subject>Plasmodium - metabolism</subject><subject>Pyrrolidines - chemical synthesis</subject><subject>Pyrrolidines - chemistry</subject><subject>Pyrrolidines - pharmacology</subject><subject>Structure-Activity Relationship</subject><issn>0022-2623</issn><issn>1520-4804</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2000</creationdate><recordtype>article</recordtype><recordid>eNpt0c1u1DAQB_AIgehSOPACyAdA3UPAH5uv3rZLC0gVrLpF4hY5ybjrxYmDxynk1itvwOPwLH0SvOyqcMAXH_yb8Wj-UfSU0VeMcvZ609JwcjHciyYs4TSe5XR2P5pQynnMUy4OokeIm2AE4-JhdMBokeWsoJPo15x8gG9kYSQisYosrYfOa2nIYm2ss18H3UF8AajRy64GcgHX4DC8z68CRKKsI8tQ3dpGy-Pbmx9kNXZ-DQhIZNeQE22NvdJ1qDi9lmaQXttu-xOLj8Ttzc_4jQa_Ho1sdWd7Z_vRTGMRH-FQodd-8NCQfg3daNo_DjqY9qNz1ugmjIaPowdKGoQn-_sw-nR2erl4F59_fPt-MT-PpchyH1dpkkIlc5k0s5qxStWQ0kqoRvAsK6qGybSuq1ylrKmrlEtgQmVZ3qh0lrMmV-Iwernr22-XAujLVmMNxsgO7IBlxnlCaVIEON3B2llEB6rsnW6lG0tGy21c5V1cwT7bNx2qFpp_5C6fAJ7vgcSwQuVCBhr_ulmRM779M96xkBJ8v3uW7kuZZiJLysvlqiwWK3qyOvtcJsG_2HlZY7mxg-vC6v4z32-1VL7B</recordid><startdate>20000907</startdate><enddate>20000907</enddate><creator>Batra, Sanjay</creator><creator>Srivastava, Pratima</creator><creator>Roy, Kamal</creator><creator>Pandey, V. 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source	American Chemical Society:Jisc Collections:American Chemical Society Read & Publish Agreement 2022-2024 (Reading list)
subjects	Animals Antibiotics. Antiinfectious agents. Antiparasitic agents Antimalarials - chemical synthesis Antimalarials - chemistry Antimalarials - pharmacology Antiparasitic agents Biological and medical sciences Chloroquine - pharmacology Drug Resistance Drug Resistance, Multiple Heme - antagonists & inhibitors Heme - metabolism Heme Oxygenase (Decyclizing) - antagonists & inhibitors Heme Oxygenase (Decyclizing) - metabolism Hemeproteins - antagonists & inhibitors Hemeproteins - metabolism Medical sciences Mice Pharmacology. Drug treatments Plasmodium - drug effects Plasmodium - metabolism Pyrrolidines - chemical synthesis Pyrrolidines - chemistry Pyrrolidines - pharmacology Structure-Activity Relationship
title	A New Class of Potential Chloroquine-Resistance Reversal Agents for Plasmodia: Syntheses and Biological Evaluation of 1-(3‘-Diethylaminopropyl)-3-(substituted phenylmethylene)pyrrolidines
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