methyl 2-(3-hydroxypropyl)oxazole-4-carboxylate | 1355026-81-1

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: methyl 2-(3-hydroxypropyl)oxazole-4-carboxylate
• 英文别名: methyl 2-(3-hydroxypropyl)-1,3-oxazole-4-carboxylate；Methyl 2-(3-hydroxypropyl)-1,3-oxazole-4-carboxylate
• CAS: 1355026-81-1
• 化学式: C₈H₁₁NO₄
• 分子量: 185.18
• InChiKey: MPPZJMYPLQTXGA-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.5
• 重原子数：
  13
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  72.6
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  methyl 2-(3-hydroxypropyl)oxazole-4-carboxylate 在 三氧化硫吡啶 、 二甲基亚砜 、 N,N-二异丙基乙胺 作用下， 以 乙酸乙酯 为溶剂， 生成 methyl 2-(3-oxopropyl)oxazole-4-carboxylate
  参考文献：
  名称：

  Discovery of a novel EP2/EP4 dual agonist with high subtype-selectivity

  摘要：

  A series of gamma-lactam prostaglandin E(1) analogs bearing a 16-phenyl moiety in the omega-chain and aryl moiety in the alpha-chain were synthesized and biologically evaluated. Among the tested compounds, gamma-lactam PGE analog 3 designed as a structural hybrid of 1 and 2 was discovered as the most optimized EP2/EP4 dual agonist with excellent subtype-selectivity (K(i) values: mEP2 = 9.3 nM, mEP4 = 0.41 nM). A structure-activity relationship study is presented. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2011.10.109
• 作为产物：
  描述：

  methyl 2-(3-((tert-butyldiphenylsilyl)oxy)propyl)oxazole-4-carboxylate 在 四丁基氟化铵 作用下， 以 四氢呋喃 为溶剂， 反应 1.0h， 以81%的产率得到methyl 2-(3-hydroxypropyl)oxazole-4-carboxylate
  参考文献：
  名称：

  [EN] CYCLOPROPYL-AMIDE COMPOUNDS AS DUAL LSD1/HDAC INHIBITORS
  [FR] COMPOSÉS CYCLOPROPYL-AMIDES UTILISÉS COMME INHIBITEURS DOUBLES DE LSD1/HDAC

  摘要：

  公开号：

  WO2017195216A4

文献信息

• Cyclopropyl-amide compounds as dual LSD1/HDAC inhibitors
  申请人：Jubilant Epicore LLC

  公开号：US11352322B2

  公开（公告）日：2022-06-07

  The present disclosure describes novel compounds of the general Formula (I), their analogs, tautomeric forms, stereoisomers, polymorphs, hydrates, solvates, pharmaceutically acceptable salts, pharmaceutical compositions, metabolites, and prodrugs thereof. These compounds can inhibit both LSD and HDAC and are useful as therpeautic or ameliorating agent for diseases that are involved in cellular growth such as malignant tumors, schizophrenia, Alzheimer's disease, parkinson's disease and the like.

  本公开描述了通式（I）的新型化合物及其类似物、同分异构体、立体异构体、多晶型、水合物、溶液、药学上可接受的盐、药物组合物、代谢物和原药。这些化合物可同时抑制 LSD 和 HDAC，可用作治疗或改善涉及细胞生长的疾病的药物，如恶性肿瘤、精神分裂症、阿尔茨海默病、帕金森病等。
• [EN] CYCLOPROPYL-AMIDE COMPOUNDS AS DUAL LSD1/HDAC INHIBITORS<br/>[FR] COMPOSÉS CYCLOPROPYL-AMIDES UTILISÉS COMME INHIBITEURS DOUBLES DE LSD1/HDAC
  申请人：JUBILANT BIOSYS LTD

  公开号：WO2017195216A4

  公开（公告）日：2018-02-22
• CYCLOPROPYL-AMIDE COMPOUNDS AS DUAL LSD1/HDAC INHIBITORS
  申请人：Jubilant Biosys Ltd.

  公开号：EP3455204A1

  公开（公告）日：2019-03-20
• Discovery of novel prostaglandin analogs as potent and selective EP2/EP4 dual agonists
  作者：Tohru Kambe、Toru Maruyama、Yoshihiko Nakai、Hideyuki Yoshida、Hiroji Oida、Takayuki Maruyama、Nobutaka Abe、Akio Nishiura、Hisao Nakai、Masaaki Toda

  DOI：10.1016/j.bmc.2012.02.018

  日期：2012.4

  To identify potent EP2/EP4 dual agonists with excellent subtype selectivity, a series of c-lactam prostaglandin E analogs bearing a 16-phenyl x-chain were synthesized and evaluated. Structural hybridization of 1 and 2, followed by more detailed chemical modification of the benzoic acid moiety, led us to the discovery of a 2-mercaptothiazole-4-carboxylic acid analog 3 as the optimal compound in the series. An isomer of this compound, the 2-mercaptothiazole-5-carboxylic acid analog 13, showed 34-fold and 13-fold less potent EP2 and EP4 receptor affinities, respectively. Structure activity relationship data from an in vitro mouse receptor binding assay are presented. Continued evaluation in an in vivo rat model of another 2-mercaptothiazole-4-carboxylic acid analog 17, optimized for sustained compound release from PLGA microspheres, demonstrated its effectiveness in a rat bone fracture-healing model following topical administration. (C) 2012 Elsevier Ltd. All rights reserved.
• Discovery of a novel EP2/EP4 dual agonist with high subtype-selectivity
  作者：Tohru Kambe、Toru Maruyama、Masayuki Nakano、Yoshihiko Nakai、Tadahiro Yoshida、Naoki Matsunaga、Hiroji Oida、Akira Konaka、Takayuki Maruyama、Hisao Nakai、Masaaki Toda

  DOI：10.1016/j.bmcl.2011.10.109

  日期：2012.1

  A series of gamma-lactam prostaglandin E(1) analogs bearing a 16-phenyl moiety in the omega-chain and aryl moiety in the alpha-chain were synthesized and biologically evaluated. Among the tested compounds, gamma-lactam PGE analog 3 designed as a structural hybrid of 1 and 2 was discovered as the most optimized EP2/EP4 dual agonist with excellent subtype-selectivity (K(i) values: mEP2 = 9.3 nM, mEP4 = 0.41 nM). A structure-activity relationship study is presented. (C) 2011 Elsevier Ltd. All rights reserved.