ethyl 4-methyl-2-phenylsulfanylthiazole-5-carboxylate | 40003-15-4

• 分子结构分类: 有机化合物 - 有机硫化合物 - 硫醚类
• 英文名称: ethyl 4-methyl-2-phenylsulfanylthiazole-5-carboxylate
• 英文别名: ethyl 2-phenylthio-4-methyl-5-thiazolecarboxylate；4-methyl-2-phenylsulfanyl-thiazole-5-carboxylic acid ethyl ester；2-Phenylthio-4-methyl-5-carbethoxythiazol；ethyl 4-methyl-2-phenylsulfanyl-1,3-thiazole-5-carboxylate
• CAS: 40003-15-4
• 化学式: C₁₃H₁₃NO₂S₂
• 分子量: 279.384
• InChiKey: NWXZLYQJUMNQSX-UHFFFAOYSA-N

物化性质

• 沸点：
  414.9±37.0 °C(Predicted)
• 密度：
  1.29±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.3
• 重原子数：
  18
• 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：
  92.7
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  ethyl 4-methyl-2-phenylsulfanylthiazole-5-carboxylate 在 lithium aluminium tetrahydride 作用下， 以 四氢呋喃 为溶剂， 反应 0.25h， 生成 ethyl 4-methyl-2-phenylsulfanylthiazole-5-methanol
  参考文献：
  名称：

  EP1403253

  摘要：

  公开号：
• 作为产物：
  描述：

  2-氨基-4-甲基噻唑-5-甲酸乙酯 在 potassium carbonate 作用下， 以 丙酮 为溶剂， 生成 ethyl 4-methyl-2-phenylsulfanylthiazole-5-carboxylate
  参考文献：
  名称：

  Abdel-Lateef,M.F.-A.; Eckstein,Z., Roczniki Chemii, 1972, vol. 46, p. 1647 - 1658

  摘要：

  DOI：

文献信息

• 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。
• Thiazole derivatives of benzoic and phenylalkanoic acids
  申请人：Shionogi & Co., Ltd.

  公开号：US04025528A1

  公开（公告）日：1977-05-24

  Thiazole derivatives represented by the general formula: ##STR1## wherein A is oxygen, sulfur, imino, or NR.sub.3, wherein R.sub.3 is C.sub.1.sub.-5 alkyl, C.sub.2.sub.-5 alkenyl, C.sub.3.sub.-5 alkynyl, C.sub.3.sub.-6 cycloalkyl-C.sub.1.sub.-3 alkyl or C.sub.7.sub.-8 aralkyl; R.sub.1 is hydrogen, C.sub.1.sub.-5 alkyl, C.sub.2.sub.-5 alkenyl, C.sub.3.sub.-5 alkynyl, C.sub.3.sub.-6 cycloalkyl-C.sub.1.sub.-3 alkyl or C.sub.7.sub.- 8 aralkyl; R.sub.2 is hydroxy, C.sub.1.sub.-5 alkoxy or OM, wherein M is alkali metal, or one equivalent of alkaline earth metal, cupric or aluminum cation; n is an integer of 0 or 1; X.sub.1 and X.sub.2 are independently hydrogen or C.sub.1.sub.-5 alkyl; Y.sub.1 and Y.sub.2 are independently hydrogen, halogen, C.sub.1.sub.-5 alkyl, C.sub.1.sub.-5 alkoxy or trifluoromethyl; and the group ##STR2## is linked to one of the meta or para positions of the benzene ring A, n is not 0 when A is imino and --CH.sub.2 --COR.sub.2 does not substitute the thiazole ring when A is imino, being useful as anti-inflammatory, anti-rheumatic, analgesic or anti-lipemia agents.

  通式表示的噻唑衍生物：##STR1## 其中A是氧、硫、亚胺或NR.sub.3，其中R.sub.3是C.sub.1.sub.-5烷基、C.sub.2.sub.-5烯基、C.sub.3.sub.-5炔基、C.sub.3.sub.-6环烷基-C.sub.1.sub.-3烷基或C.sub.7.sub.-8芳基烷基；R.sub.1是氢、C.sub.1.sub.-5烷基、C.sub.2.sub.-5烯基、C.sub.3.sub.-5炔基、C.sub.3.sub.-6环烷基-C.sub.1.sub.-3烷基或C.sub.7.sub.-8芳基烷基；R.sub.2是羟基、C.sub.1.sub.-5烷氧基或OM，其中M是碱金属或一当量的碱土金属、铜离子或铝离子；n是0或1的整数；X.sub.1和X.sub.2独立地是氢或C.sub.1.sub.-5烷基；Y.sub.1和Y.sub.2独立地是氢、卤素、C.sub.1.sub.-5烷基、C.sub.1.sub.-5烷氧基或三氟甲基；以及##STR2## 这个基团连接到苯环A的meta或para位置之一，当A是亚胺时，n不是0，当A是亚胺时，--CH.sub.2 --COR.sub.2不替换噻唑环，这些化合物可用作抗炎、抗风湿、止痛或抗脂质血症剂。
• Thiazole derivatives
  申请人：Shionogi & Co., Ltd.

  公开号：US04077968A1

  公开（公告）日：1978-03-07

  Thiazole derivatives represented by the general formula: ##STR1## wherein A is oxygen, sulfur, imino, or NR.sub.3, wherein R.sub.3 is C.sub.1-5 alkyl, C.sub.2-5 alkenyl, C.sub.3-5 alkynyl, C.sub.3-6 cycloalkyl-C.sub.1-3 alkyl or C.sub.7-8 aralkyl; R.sub.1 is hydrogen, C.sub.1-5 alkyl, C.sub.2-5 alkenyl, C.sub.3-5 alkynyl, C.sub.3-6 cycloalkyl-C.sub.1-3 alkyl or C.sub.7-8 aralkyl; R.sub.2 is hydroxy, C.sub.1-5 alkoxy or OM, wherein M is alkali metal, or one equivalent of alkaline earth metal, cupric or aluminum cation; n is an integer of 0 or 1; X.sub.1 and X.sub.2 are independently hydrogen or C.sub.1-5 alkyl; Y.sub.1 and Y.sub.2 are independently hydrogen, halogen, C.sub.1-5 alkyl, C.sub.1-5 alkoxy or trifluoromethyl; and the group ##STR2## is linked to one of the meta or para positions of the benzene ring A, n is not 0 when A is imino and --CH.sub.2 --COR.sub.2 does not substitute the thiazole ring when A is imino, being useful as anti-inflammatory, anti-rheumatic, analgesic or anti-lipemia agents.

  通式表示的噻唑衍生物：##STR1## 其中A为氧、硫、亚胺或NR.sub.3，其中R.sub.3为C.sub.1-5烷基、C.sub.2-5烯基、C.sub.3-5炔基、C.sub.3-6环烷基-C.sub.1-3烷基或C.sub.7-8芳基烷基；R.sub.1为氢、C.sub.1-5烷基、C.sub.2-5烯基、C.sub.3-5炔基、C.sub.3-6环烷基-C.sub.1-3烷基或C.sub.7-8芳基烷基；R.sub.2为羟基、C.sub.1-5烷氧基或OM，其中M为碱金属或一当量的碱土金属、铜或铝阳离子；n为0或1的整数；X.sub.1和X.sub.2独立地为氢或C.sub.1-5烷基；Y.sub.1和Y.sub.2独立地为氢、卤素、C.sub.1-5烷基、C.sub.1-5烷氧基或三氟甲基；和 ##STR2## 链接到苯环A的其中一个间位或对位，当A为亚胺时，n不为0，且当A为亚胺时，--CH.sub.2--COR.sub.2不取代噻唑环，用作抗炎、抗风湿、镇痛或抗脂质血症剂。
• Heterocyclic compound and medicinal use thereof
  申请人：Kyoto Pharmaceutical Industries, Ltd.

  公开号：US07557123B2

  公开（公告）日：2009-07-07

  The novel heterocyclic compound of the present invention is a novel heterocyclic compound having the formula (I) Y: 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，其中Y：R15-C(R14)=N-O-，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是以下基团，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至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，抗动脉粥样硬化剂，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 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。