Methyl 3-(pyridin-3-yl)-1,2-oxazole-5-carboxylate | 330558-59-3

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡啶及其衍生物
• 英文名称: Methyl 3-(pyridin-3-yl)-1,2-oxazole-5-carboxylate
• 英文别名: methyl 3-pyridin-3-yl-1,2-oxazole-5-carboxylate
• CAS: 330558-59-3
• 化学式: C₁₀H₈N₂O₃
• mdl: MFCD01932674
• 分子量: 204.185
• InChiKey: MFRGXLRFFUONRQ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.1
• 重原子数：
  15
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.1
• 拓扑面积：
  65.2
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  Methyl 3-(pyridin-3-yl)-1,2-oxazole-5-carboxylate 在 甲醇 、 lithium hydroxide 作用下， 以 四氢呋喃 为溶剂， 生成 3-(pyridin-3-yl)isoxazole-5-carboxylic acid
  参考文献：
  名称：

  Novel non-peptidic vinylsulfones targeting the S2 and S3 subsites of parasite cysteine proteases

  摘要：

  We describe here the identification of non-peptidic vinylsulfones that inhibit parasite cysteine proteases in vitro and inhibit the growth of Trypanosoma brucei brucei parasites in culture. A high resolution (1.75 angstrom) co-crystal structure of 8a bound to cruzain reveals how the non-peptidic P2/P3 moiety in such analogs bind the S2 and S3 subsites of the protease, effectively recapitulating important binding interactions present in more traditional peptide-based protease inhibitors and natural substrates. (c) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2009.08.098
• 作为产物：
  描述：

  丙炔酸甲酯 、 3-吡啶醛肟 在 N-氯代丁二酰亚胺 、 三乙胺 作用下， 以 N,N-二甲基甲酰胺 、 二氯甲烷 为溶剂， 生成 Methyl 3-(pyridin-3-yl)-1,2-oxazole-5-carboxylate
  参考文献：
  名称：

  Novel non-peptidic vinylsulfones targeting the S2 and S3 subsites of parasite cysteine proteases

  摘要：

  We describe here the identification of non-peptidic vinylsulfones that inhibit parasite cysteine proteases in vitro and inhibit the growth of Trypanosoma brucei brucei parasites in culture. A high resolution (1.75 angstrom) co-crystal structure of 8a bound to cruzain reveals how the non-peptidic P2/P3 moiety in such analogs bind the S2 and S3 subsites of the protease, effectively recapitulating important binding interactions present in more traditional peptide-based protease inhibitors and natural substrates. (c) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2009.08.098

文献信息

• Novel non-peptidic vinylsulfones targeting the S2 and S3 subsites of parasite cysteine proteases
  作者：Clifford Bryant、Iain D. Kerr、Moumita Debnath、Kenny K.H. Ang、Joseline Ratnam、Rafaela S. Ferreira、Priyadarshini Jaishankar、DongMei Zhao、Michelle R. Arkin、James H. McKerrow、Linda S. Brinen、Adam R. Renslo

  DOI：10.1016/j.bmcl.2009.08.098

  日期：2009.11

  We describe here the identification of non-peptidic vinylsulfones that inhibit parasite cysteine proteases in vitro and inhibit the growth of Trypanosoma brucei brucei parasites in culture. A high resolution (1.75 angstrom) co-crystal structure of 8a bound to cruzain reveals how the non-peptidic P2/P3 moiety in such analogs bind the S2 and S3 subsites of the protease, effectively recapitulating important binding interactions present in more traditional peptide-based protease inhibitors and natural substrates. (c) 2009 Elsevier Ltd. All rights reserved.