methyl 2-(pyridine-3-yl)oxazole-4-carboxylate | 1065102-69-3

• 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-(pyridine-3-yl)oxazole-4-carboxylate
• 英文别名: methyl 2-(pyridin-3-yl)-1,3-oxazole-4-carboxylate；Methyl 2-(pyridin-3-YL)oxazole-4-carboxylate；methyl 2-pyridin-3-yl-1,3-oxazole-4-carboxylate
• CAS: 1065102-69-3
• 化学式: C₁₀H₈N₂O₃
• 分子量: 204.185
• InChiKey: PICLJYXRBUEJGG-UHFFFAOYSA-N

物化性质

• 沸点：
  356.1±48.0 °C(Predicted)
• 密度：
  1.261±0.06 g/cm3(Predicted)

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 2-(pyridine-3-yl)oxazole-4-carboxylate 在 lithium aluminium tetrahydride 、 氯化亚砜 、 sodium hydroxide 作用下， 以 四氢呋喃 、 二氯甲烷 、 水 、 乙腈 为溶剂， 反应 6.0h， 生成 (2,3-dihydrobenzo[b][1,4]dioxin-6-yl)(1-((2-(pyridin-3-yl)oxazol-4-yl)methyl)piperidin-4-yl)methanone
  参考文献：
  名称：

  Discovery of the disubstituted oxazole analogues as a novel class anti-tuberculotic agents against MDR- and XDR-MTB

  摘要：

  A high-throughput screening effort on 45,000 compounds resulted in the discovery of a disubstituted oxazole as a new structural class inhibitor of Mycobacterium tuberculosis (Mtb). In order to improve the activity and investigate the SAR of this scaffold, a series of disubstituted azole analogues have been designed and synthesized. The newly synthesized compounds 1a-y were evaluated for their in vitro anti-TB activity versus replicating, multi-and extensive drug resistant Mtb strains. All the compounds, except 1o, 1p and 1q, showed potent anti-TB activity with MIC of 1-64 mg/L. The test of broad spectrum panel revealed that this series are specific to Mtb. The cytotoxicity assessment indicated that the compounds were not cytotoxic against HEK 293 cells. The compounds could have a novel mechanism to anti-Mtb as they can inhibit drug sensitive and drug resistant Mtb. (C) 2015 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2015.09.072
• 作为产物：
  描述：

  3-吡啶甲醛 、 L-丝氨酸甲酯盐酸盐 在 magnesium sulfate 、 三乙胺 、 三氯溴甲烷 、 1,8-二氮杂双环[5.4.0]十一碳-7-烯 作用下， 以 四氢呋喃 、 N,N-二甲基乙酰胺 为溶剂， 以34.2 %的产率得到methyl 2-(pyridine-3-yl)oxazole-4-carboxylate
  参考文献：
  名称：

  [EN] PHARMACEUTICAL COMPOUNDS FOR THE TREATMENT OF COMPLEMENT MEDIATED DISORDERS
  [FR] COMPOSÉS PHARMACEUTIQUES POUR LE TRAITEMENT DE TROUBLES MÉDIÉS PAR LE COMPLÉMENT

  摘要：

  This disclosure provides compounds, compositions, and methods to treat medical disorders, such as complement-mediated disorders, including complement C1s-mediated disorders.

  公开号：

  WO2024035686A1

文献信息

• [EN] PHARMACEUTICAL COMPOUNDS FOR THE TREATMENT OF COMPLEMENT MEDIATED DISORDERS<br/>[FR] COMPOSÉS PHARMACEUTIQUES POUR LE TRAITEMENT DE TROUBLES MÉDIÉS PAR LE COMPLÉMENT
  申请人：[en]ALEXION PHARMACEUTICALS, INC.

  公开号：WO2024035686A1

  公开（公告）日：2024-02-15

  This disclosure provides compounds, compositions, and methods to treat medical disorders, such as complement-mediated disorders, including complement C1s-mediated disorders.
• A Direct Synthesis of Oxazoles from Aldehydes
  作者：Thomas H. Graham

  DOI：10.1021/ol101346w

  日期：2010.8.20

  An expedient method for the direct conversion of aldehydes to 2,4-disubstituted oxazoles is presented. The method relies on the oxidation of an oxazolidine formed from the condensation of serine with an aldehyde and proceeds through a 2,5-dihydrooxazole intermediate. In contrast to standard methods that start from carboxylic acids, the use of aldehydes as starting materials does not require intermediate purification and affords the oxazoles under relatively mild conditions.
• Discovery of the disubstituted oxazole analogues as a novel class anti-tuberculotic agents against MDR- and XDR-MTB
  作者：Dongsheng Li、Nana Gao、Ningyu Zhu、Yuan Lin、Yan Li、Minghua Chen、Xuefu You、Yu Lu、Kanglin Wan、Jian-Dong Jiang、Wei Jiang、Shuyi Si

  DOI：10.1016/j.bmcl.2015.09.072

  日期：2015.11

  A high-throughput screening effort on 45,000 compounds resulted in the discovery of a disubstituted oxazole as a new structural class inhibitor of Mycobacterium tuberculosis (Mtb). In order to improve the activity and investigate the SAR of this scaffold, a series of disubstituted azole analogues have been designed and synthesized. The newly synthesized compounds 1a-y were evaluated for their in vitro anti-TB activity versus replicating, multi-and extensive drug resistant Mtb strains. All the compounds, except 1o, 1p and 1q, showed potent anti-TB activity with MIC of 1-64 mg/L. The test of broad spectrum panel revealed that this series are specific to Mtb. The cytotoxicity assessment indicated that the compounds were not cytotoxic against HEK 293 cells. The compounds could have a novel mechanism to anti-Mtb as they can inhibit drug sensitive and drug resistant Mtb. (C) 2015 Elsevier Ltd. All rights reserved.