5-苯基-3-异恶唑乙酸乙酯 | 3929-70-2

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 中文名称: 5-苯基-3-异恶唑乙酸乙酯
• 英文名称: ethyl 5-phenyl-3-isoxazoleacetate
• 英文别名: Ethyl 2-(5-phenylisoxazol-3-yl)acetate；ethyl 2-(5-phenyl-1,2-oxazol-3-yl)acetate
• CAS: 3929-70-2
• 化学式: C₁₃H₁₃NO₃
• 分子量: 231.251
• InChiKey: PFTPHIQOMIWIMI-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.2
• 重原子数：
  17
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.23
• 拓扑面积：
  52.3
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  5-苯基-3-异恶唑乙酸乙酯 生成 3-(3-Chloroethyl)-5-phenylisoxazole
  参考文献：
  名称：

  异恶唑。十八。5-氨基烷基和3-氨基烷基异恶唑及其衍生物的合成和药理性质。

  摘要：

  DOI：

  10.1021/jm00315a028
• 作为产物：
  描述：

  ethyl 5-phenyl-3,5-dioxopentanoate 在 盐酸羟胺 作用下， 以 吡啶 为溶剂， 以6.9 g的产率得到5-苯基-3-异恶唑乙酸乙酯
  参考文献：
  名称：

  2-(2-Aryl-2-oxoethylidene)-1,2,3,4-tetrahydropyridines. Novel isomers of 1,4-dihydropyridine calcium channel blockers

  摘要：

  The title compounds are novel double bond isomers of 1,4-dihydropyridine-type calcium channel blockers (CCB). These derivatives were prepared by using the Hantzsch dihydropyridine synthesis. The assignment of structure was based on spectroscopic data and a regiochemically unambiguous synthesis. Several of the analogues inhibited [3H]nitrendipine binding with IC50 values as low as 25 nM. By comparison, nifedipine, a clinically useful 1,4-dihydropyridine CCB, inhibits [3H]nitrendipine binding with an IC50 of 1.6 nM. In the Langendorff rat heart preparation, treatment with the more potent derivatives produced marked dose-related increases in coronary flow with little or no effect on heart rate or contractility, except at the highest concentrations tested. The selectivity for vascular versus cardiac effects was similar to that of nifedipine, i.e., the concentration producing vasodilation was approximately 2 orders of magnitude lower than the concentration eliciting cardiodepression. These novel isomers extend the structure-activity relationships for calcium channel blockers into a series closely related to the 1,4-dihydropyridines.

  DOI：

  10.1021/jm00403a030

文献信息

• [EN] IL4I1 INHIBITORS AND METHODS OF USE<br/>[FR] INHIBITEURS D'IL4I1 ET PROCÉDÉS D'UTILISATION
  申请人：MERCK SHARP & DOHME LLC

  公开号：WO2022232333A1

  公开（公告）日：2022-11-03

  Described herein are compounds of Formula (I) or a pharmaceutically acceptable salt thereof, wherein R1, R2, R3, R4, R5, L, X and Y are as defined herein. The compounds of Formula (I) act as IL4I1 inhibitors and can be useful in preventing, treating or acting as a remedial agent for IL4I1-related diseases. Also provided herein are pharmaceutical compositions comprising the compounds of the invention, or their pharmaceutically acceptable salts, and a pharmaceutically acceptable carrier and methods of treatment with the compounds of the invention.

  以下是公式（I）的化合物或其药学上可接受的盐，其中R1、R2、R3、R4、R5、L、X和Y的定义如下。公式（I）的化合物作为IL4I1抑制剂，可用于预防、治疗或作为治疗IL4I1相关疾病的治疗剂。本文还提供了包含本发明化合物或其药学上可接受的盐及药学上可接受的载体的制药组合物，以及使用本发明化合物进行治疗的方法。
• Isoxazoles. XVIII. Synthesis and Pharmacological Properties of 5-Aminoalkyl- and 3-Aminoalkylisoxazoles and Related Derivatives
  作者：Hideo. Kan[UNK]o、Ikuo. Adachi、Ryonosuke. Kido、Katumi. Hirose

  DOI：10.1021/jm00315a028

  日期：1967.5
• 2-(2-Aryl-2-oxoethylidene)-1,2,3,4-tetrahydropyridines. Novel isomers of 1,4-dihydropyridine calcium channel blockers
  作者：Michael D. Taylor、Edward W. Badger、Robert P. Steffen、Stephen J. Haleen、Thomas A. Pugsley、Yu Hsin Shih、Ronald E. Weishaar

  DOI：10.1021/jm00403a030

  日期：1988.8

  The title compounds are novel double bond isomers of 1,4-dihydropyridine-type calcium channel blockers (CCB). These derivatives were prepared by using the Hantzsch dihydropyridine synthesis. The assignment of structure was based on spectroscopic data and a regiochemically unambiguous synthesis. Several of the analogues inhibited [3H]nitrendipine binding with IC50 values as low as 25 nM. By comparison, nifedipine, a clinically useful 1,4-dihydropyridine CCB, inhibits [3H]nitrendipine binding with an IC50 of 1.6 nM. In the Langendorff rat heart preparation, treatment with the more potent derivatives produced marked dose-related increases in coronary flow with little or no effect on heart rate or contractility, except at the highest concentrations tested. The selectivity for vascular versus cardiac effects was similar to that of nifedipine, i.e., the concentration producing vasodilation was approximately 2 orders of magnitude lower than the concentration eliciting cardiodepression. These novel isomers extend the structure-activity relationships for calcium channel blockers into a series closely related to the 1,4-dihydropyridines.