5-methyl-2-styryl-4-oxazoleacetic acid | 89723-89-7

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: 5-methyl-2-styryl-4-oxazoleacetic acid
• 英文别名: 2-[5-methyl-2-[(E)-2-phenylethenyl]-1,3-oxazol-4-yl]acetic acid
• CAS: 89723-89-7
• 化学式: C₁₄H₁₃NO₃
• 分子量: 243.262
• InChiKey: JXWBMJHCIPVTFX-BQYQJAHWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  18
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.14
• 拓扑面积：
  63.3
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  4-chloromethyl-5-methyl-2-styryloxazole 在 sodium hydroxide 作用下， 以 乙醇 、 二甲基亚砜 为溶剂， 反应 4.5h， 生成 5-methyl-2-styryl-4-oxazoleacetic acid
  参考文献：
  名称：

  抗糖尿病药的研究。七。4-恶唑乙酸衍生物的合成及其降血糖活性。

  摘要：

  作为寻找新型抗糖尿病药物的一部分，合成了4-噁唑烷酮酸衍生物（III），并在小鼠中测试了其降血糖活性。具有2-位为苯乙烯或合适脂肪族烃基的4-噁唑乙酸（IIIb）显示出强大的活性。这些化合物的合成及其构效关系在此呈现。

  DOI：

  10.1248/cpb.34.2840

文献信息

• Oxazoleacetic acid derivatives
  申请人：Takeda Chemical Industries, Ltd.

  公开号：US04602027A1

  公开（公告）日：1986-07-22

  A compound of the formula: ##STR1## wherein R.sup.1 is (A) a group of the formula, ##STR2## wherein R.sup.4 is H, a halogen or trifluoromethyl group, or (B) a group of the formula, ##STR3## wherein n is 0 or an integer of 1 to 3; R.sup.5 is H or an alkyl group of 1 to 6 carbon atoms; respective R.sup.6 and R.sup.7 are an alkyl group of 1 to 6 carbon atoms, an alkenyl group of 2 to 6 carbon atoms, a cycloalkyl group of 3 to 7 carbon atoms, or a cycloalkenyl group of 5 to 7 carbon atoms; R.sup.6 and R.sup.7 may be combined with the neighboring carbon atom to represent a cycloalkyl group of 3 to 7 carbon atoms; a cycloalkenyl group of 5 to 7 carbon atoms, a bicycloalkyl group of 7 to 10 carbon atoms, or a bicycloalkenyl group of 7 to 10 carbon atoms; R.sup.2 is an alkyl group of 1 to 6 carbon atoms; and R.sup.3 is H, an alkyl group of 1 to 6 carbon atoms or an aralkyl group, or a pharmaceutically acceptable salt thereof. The compound has hypoglycemic, glucose tolerance improving and insulin sensitivity potentiating activities.

  一种化合物的通式为：##STR1## 其中R1为（A）通式为 ##STR2## 的基团，其中R4为H、卤素或三氟甲基；或（B）通式为 ##STR3## 的基团，其中n为0或1至3的整数；R5为H或1至6个碳原子的烷基；各自独立的R6和R7为1至6个碳原子的烷基、2至6个碳原子的烯基、3至7个碳原子的环烷基或5至7个碳原子的环烯基；R6和R7可以与相邻的碳原子结合，代表3至7个碳原子的环烷基、5至7个碳原子的环烯基、7至10个碳原子的二环烷基或7至10个碳原子的二环烯基；R2为1至6个碳原子的烷基；R3为H、1至6个碳原子的烷基或芳烷基，或其药学上可接受的盐。该化合物具有降血糖、改善葡萄糖耐量和增强胰岛素敏感性的活性。
• Novel heterocyclic compound and medicinal use thereof
  申请人：——

  公开号：US20040220215A1

  公开（公告）日：2004-11-04

  The novel heterocyclic compound of the present invention is a novel heterocyclic compound having the formula (I) 1 Y: 2 wherein R 1 is H or C 1-6 alkyl, R 2 is H, —CO—C(R 4 )═C(R 4 )—R 5 wherein R 4 is H or C 1-4 alkyl, and R 5 is C 4-8 alkyl, C 2-8 alkenyl and the like, and the like, Y is the following group wherein X is O or S, R 7 is the same as R 4 , R 8 is R 10 —C(R 9 )═C(R 9 )— wherein R 9 is the same as R 4 , R 10 is C 3-6 alkyl and the like, and the like, R 14 is the same as R 4 , and R 15 is aryl and the like, Y—(CH 2 )n-O— is bonded to the 6- or 7-position of the tetrahydroisoquinoline skeleton, and n is an integer of 1 to 4, or a pharmaceutically acceptable salt thereof. The compound (I) of the present invention is useful as a hypoglycemic agent, a hypolipidemic agent, an insulin resistance improver, a therapeutic agent of diabetes, a therapeutic agent of diabetic complications, a glucose tolerance improver, an anti-arteriosclerosis agent, an anti-obesity agent, an antiinflammatory agent, an agent for the prophylaxis or treatment of PPAR-mediated diseases or an agent for the prophylaxis or treatment of syndrome X.

  本发明的新型杂环化合物是一种具有以下式子(I)1Y:2的新型杂环化合物，其中R1为H或C1-6烷基，R2为H，-CO-C(R4)═C(R4)-R5，其中R4为H或C1-4烷基，R5为C4-8烷基、C2-8烯基等，Y为以下基团，其中X为O或S，R7与R4相同，R8为R10-C(R9)═C(R9)-，其中R9与R4相同，R10为C3-6烷基等，R14与R4相同，R15为芳基等，Y-(CH2)n-O-与四氢异喹啉骨架的6-或7-位结合，n为1到4的整数，或其药学上可接受的盐。本发明的化合物(I)可用作降血糖剂、降血脂剂、胰岛素抵抗改善剂、糖尿病治疗剂、糖尿病并发症治疗剂、葡萄糖耐受改善剂、抗动脉硬化剂、抗肥胖剂、抗炎剂、PPAR介导疾病的预防或治疗剂或综合征X的预防或治疗剂。
• NOVEL THIAZOLIDINEDIONE COMPOUND AND USE THEREOF
  申请人：Japan Tobacco Inc.

  公开号：EP0603419A1

  公开（公告）日：1994-06-29

  A novel thiazolidinedione compound represented by general formula (I), a pharmaceutically acceptable salt thereof, and a pharmaceutical composition thereof; wherein R represents an aromatic, cycloaliphatic or heteroaromatic hydrocarbon group which may be substituted; R₁ and R₂ represent each independently hydrogen, lower alkyl, or an aromatic or heteroaromatic hydrocarbon group which may be substituted by lower alkyl, acyl, lower alkoxy, cyano, nitro, lower alkoxycarbonyl or sulfonyl; R₃ represents hydrogen, hydroxy, lower alkyl, acyl, lower alkoxy, cyano, nitro, lower alkoxycarbonyl or sulfonyl; R₄ represents lower alkyl; X represents oxygen, sulfur or sec. amino; A represents (CH₂)m (wherein m is an integer of 0, 1, or 2); and B represents (CH₂)n (wherein n is an integer of 0, 1 or 2). This compound is excellent in hypoglycemic and hypolipemic effects, so that it is useful for treating diabetes, preventing and treating the complications of diabetes, and treating hyperlipemia.

  一种由通式(I)代表的新型噻唑烷二酮化合物、其药学上可接受的盐及其药物组合物；其中 R 代表可被取代的芳族、环脂族或杂芳族烃基；R₁和 R₂ 各自独立地代表氢、低级烷基或可被低级烷基、酰基、低级烷氧基、氰基、硝基、低级烷氧羰基或磺酰基取代的芳香族或杂芳族烃基； R₃ 代表氢、羟基、低级烷基、酰基、低级烷氧基、氰基、硝基、低级烷氧羰基或磺酰基； R₄ 代表低级烷基； X 代表氧、硫或仲烷基； A 代表 (CH₄)氨基；A 代表 (CH₂)m（其中 m 为 0、1 或 2 的整数）；B 代表 (CH₂)n（其中 n 为 0、1 或 2 的整数）。该化合物具有良好的降血糖和降血脂作用，因此可用于治疗糖尿病、预防和治疗糖尿病并发症以及治疗高脂血症。
• NOVEL HETEROCYCLIC COMPOUND AND MEDICINAL USE THEREOF
  申请人：Kyoto Pharmaceutical Industries, Ltd.

  公开号：EP1403253A1

  公开（公告）日：2004-03-31

  The novel heterocyclic compound of the present invention is a novel heterocyclic compound having the formula (I)         R15―C(R14)=N-O― wherein R1 is H or C1-6 alkyl, R2 is H, -CO-C(R4)=C(R4)-R5 wherein R4 is H or C1-4 alkyl, and R5 is C4-8 alkyl, C2-8 alkenyl and the like, and the like, Y is the following group wherein X is O or S, R7 is the same as R4, R8 is R10-C(R9)=C(R9)- wherein R9 is the same as R4, R10 is C3-6 alkyl and the like, and the like, R14 is the same as R4, and R15 is aryl and the like, Y-(CH2)n-O- is bonded to the 6- or 7-position of the tetrahydroisoquinoline skeleton, and n is an integer of 1 to 4, or a pharmaceutically acceptable salt thereof. The compound (I) of the present invention is useful as a hypoglycemic agent, a hypolipidemic agent, an insulin resistance improver, a therapeutic agent of diabetes, a therapeutic agent of diabetic complications, a glucose tolerance improver, an anti-arteriosclerosis agent, an anti-obesity agent, an antiinflammatory agent, an agent for the prophylaxis or treatment of PPAR-mediated diseases or an agent for the prophylaxis or treatment of syndrome X.

  本发明的新型杂环化合物是一种具有式 (I) 的新型杂环化合物 r15-c(r14)=n-o- 其中 R1 是 H 或 C1-6 烷基，R2 是 H、-CO-C(R4)=C(R4)-R5 其中 R4 是 H 或 C1-4 烷基，R5 是 C4-8 烷基、C2-8 烯基及类似物及类似物，Y 是以下基团 其中 X 是 O 或 S，R7 与 R4 相同，R8 是 R10-C(R9)=C(R9)- 其中 R9 与 R4 相同、R10为C3-6烷基等，R14与R4相同，R15为芳基等，Y-(CH2)n-O-键合在四氢异喹啉骨架的6位或7位，n为1～4的整数，或其药学上可接受的盐。本发明的化合物（I）可用作降血糖剂、降血脂剂、胰岛素抵抗改善剂、糖尿病治疗剂、糖尿病并发症治疗剂、葡萄糖耐量改善剂、抗动脉硬化剂、抗肥胖剂、抗炎剂、预防或治疗 PPAR 介导的疾病的药物或预防或治疗 X 综合征的药物。
• MEHGURO, KANDZI;FUDZITA, GO
  作者：MEHGURO, KANDZI、FUDZITA, GO

  DOI：——

  日期：——