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Design, synthesis, and pharmacological evaluation of benzamide derivatives as glucokinase activators.

A series of benzamide derivatives were assembled by using the privileged-fragment-merging (PFM) strategy and their SAR studies as glucokinase activators were described. Compounds 5 and 16b were identified having a suitable balance of potency and activation profile. They showed EC(50) values of 28.3... Full description

Journal Title: Bioorganic & medicinal chemistry May 1, 2012, Vol.20(9), pp.2982-2991
Main Author: Mao, Weiwei
Other Authors: Ning, Mengmeng , Liu, Zhiqing , Zhu, Qingzhang , Leng, Ying , Zhang, Ao
Format: Electronic Article Electronic Article
Language: English
Subjects:
ID: E-ISSN: 1464-3391 ; DOI: 10.1016/j.bmc.2012.03.008
Link: http://search.proquest.com/docview/1009127616/?pq-origsite=primo
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title: Design, synthesis, and pharmacological evaluation of benzamide derivatives as glucokinase activators.
format: Article
creator:
  • Mao, Weiwei
  • Ning, Mengmeng
  • Liu, Zhiqing
  • Zhu, Qingzhang
  • Leng, Ying
  • Zhang, Ao
subjects:
  • Animals–Blood
  • Benzamides–Chemical Synthesis
  • Biological Availability–Chemistry
  • Drug Design–Pharmacokinetics
  • Enzyme Activation–Pharmacology
  • Glucokinase–Drug Effects
  • Hypoglycemic Agents–Chemistry
  • Mice–Metabolism
  • Mice, Inbred Icr–Blood
  • Structure-Activity Relationship–Chemical Synthesis
  • Thiazoles–Pharmacokinetics
  • Thiazoles–Pharmacology
  • Thiazoles–Blood
  • Thiazoles–Chemical Synthesis
  • Thiazoles–Chemistry
  • Thiazoles–Pharmacokinetics
  • Thiazoles–Pharmacology
  • (S)-3-(4-((3-Fluoropyrrolidin-1-Yl)Sulfonyl)Phenoxy)-5-((3-Methylbut-2-En-1-Yl)Oxy)-N-(Thiazol-2-Yl)Benzamide
  • 3-(4-(Cyclopropylsulfonyl)Phenoxy)-5-((3-Methylbut-2-En-1-Yl)Oxy)-N-(Thiazol-2-Yl)Benzamide
  • Benzamides
ispartof: Bioorganic & medicinal chemistry, May 1, 2012, Vol.20(9), pp.2982-2991
description: A series of benzamide derivatives were assembled by using the privileged-fragment-merging (PFM) strategy and their SAR studies as glucokinase activators were described. Compounds 5 and 16b were identified having a suitable balance of potency and activation profile. They showed EC(50) values of 28.3 and 44.8 nM, and activation folds of 2.4 and 2.2, respectively. However, both compounds displayed a minor reduction in plasma glucose levels on imprinting control region (ICR) mice. Unfavorable pharmacokinetic profiles (PK) were also observed on these two compounds.
language: eng
source:
identifier: E-ISSN: 1464-3391 ; DOI: 10.1016/j.bmc.2012.03.008
fulltext: fulltext
issn:
  • 14643391
  • 1464-3391
url: Link


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titleDesign, synthesis, and pharmacological evaluation of benzamide derivatives as glucokinase activators.
creatorMao, Weiwei ; Ning, Mengmeng ; Liu, Zhiqing ; Zhu, Qingzhang ; Leng, Ying ; Zhang, Ao
contributorMao, Weiwei (correspondence author) ; Mao, Weiwei (record owner)
ispartofBioorganic & medicinal chemistry, May 1, 2012, Vol.20(9), pp.2982-2991
identifierE-ISSN: 1464-3391 ; DOI: 10.1016/j.bmc.2012.03.008
subjectAnimals–Blood ; Benzamides–Chemical Synthesis ; Biological Availability–Chemistry ; Drug Design–Pharmacokinetics ; Enzyme Activation–Pharmacology ; Glucokinase–Drug Effects ; Hypoglycemic Agents–Chemistry ; Mice–Metabolism ; Mice, Inbred Icr–Blood ; Structure-Activity Relationship–Chemical Synthesis ; Thiazoles–Pharmacokinetics ; Thiazoles–Pharmacology ; Thiazoles–Blood ; Thiazoles–Chemical Synthesis ; Thiazoles–Chemistry ; Thiazoles–Pharmacokinetics ; Thiazoles–Pharmacology ; (S)-3-(4-((3-Fluoropyrrolidin-1-Yl)Sulfonyl)Phenoxy)-5-((3-Methylbut-2-En-1-Yl)Oxy)-N-(Thiazol-2-Yl)Benzamide ; 3-(4-(Cyclopropylsulfonyl)Phenoxy)-5-((3-Methylbut-2-En-1-Yl)Oxy)-N-(Thiazol-2-Yl)Benzamide ; Benzamides
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descriptionA series of benzamide derivatives were assembled by using the privileged-fragment-merging (PFM) strategy and their SAR studies as glucokinase activators were described. Compounds 5 and 16b were identified having a suitable balance of potency and activation profile. They showed EC(50) values of 28.3 and 44.8 nM, and activation folds of 2.4 and 2.2, respectively. However, both compounds displayed a minor reduction in plasma glucose levels on imprinting control region (ICR) mice. Unfavorable pharmacokinetic profiles (PK) were also observed on these two compounds.
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15(S)-3-(4-((3-Fluoropyrrolidin-1-Yl)Sulfonyl)Phenoxy)-5-((3-Methylbut-2-En-1-Yl)Oxy)-N-(Thiazol-2-Yl)Benzamide
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