5-溴-2-氯-3-(4-乙基苄基)噻吩 | 1057216-05-3

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 噻吩类
• 中文名称: 5-溴-2-氯-3-(4-乙基苄基)噻吩
• 英文名称: 5-bromo-2-chloro-3-(4-ethylbenzyl)thiophene
• 英文别名: 5-Bromo-2-chloro-3-[(4-ethylphenyl)methyl]thiophene
• CAS: 1057216-05-3
• 化学式: C₁₃H₁₂BrClS
• 分子量: 315.661
• InChiKey: LWMFLTCOJGWAPO-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.3
• 重原子数：
  16
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.23
• 拓扑面积：
  28.2
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  5-溴-2-氯-3-(4-乙基苄基)噻吩 在 bis-triphenylphosphine-palladium(II) chloride 、 硼烷四氢呋喃络合物 、 四丁基氟化铵 、 sodium carbonate 作用下， 以 四氢呋喃 、 乙二醇二甲醚 、 水 为溶剂， 反应 7.0h， 生成 (1S)-1,5-anhydro-1-[5-chloro-4-(4-ethylbenzyl)-2-thienyl]-D-glucitol
  参考文献：
  名称：

  Synthesis and Biological Evaluation of Thiophene-<i>C</i>-glucosides as Sodium-Dependent Glucose Cotransporter 2 Inhibitors

  摘要：

  对噻吩-C-葡萄糖苷的合成和结构-活性关系（SAR）进行了探讨，并评估了 3a-f 的人钠依赖性葡萄糖共转运体 2（hSGLT2）抑制活性和大鼠尿糖排泄（UGE）效应。结果表明，3a-f 具有良好的 hSGLT2 抑制活性和大鼠尿糖排泄效应。其中，氯噻吩衍生物 3f 对 hSGLT2 具有显著的抑制活性。

  DOI：

  10.1248/cpb.c13-00407
• 作为产物：
  描述：

  4-乙基苯基溴化镁 在 三乙基硅烷 、 三氟化硼乙醚 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 1.5h， 生成 5-溴-2-氯-3-(4-乙基苄基)噻吩
  参考文献：
  名称：

  Synthesis and Biological Evaluation of Thiophene-<i>C</i>-glucosides as Sodium-Dependent Glucose Cotransporter 2 Inhibitors

  摘要：

  对噻吩-C-葡萄糖苷的合成和结构-活性关系（SAR）进行了探讨，并评估了 3a-f 的人钠依赖性葡萄糖共转运体 2（hSGLT2）抑制活性和大鼠尿糖排泄（UGE）效应。结果表明，3a-f 具有良好的 hSGLT2 抑制活性和大鼠尿糖排泄效应。其中，氯噻吩衍生物 3f 对 hSGLT2 具有显著的抑制活性。

  DOI：

  10.1248/cpb.c13-00407

文献信息

• [EN] NOVEL COMPOUNDS HAVING INHIBITORY ACTIVITY AGAINST SODIUM-DEPENDANT TRANSPORTER<br/>[FR] NOUVEAUX COMPOSES POSSEDANT UNE ACTIVITE INHIBITRICE DIRIGEE CONTRE LE TRANSPORTEUR DEPENDANT DU SODIUM
  申请人：TANABE SEIYAKU CO

  公开号：WO2005012326A1

  公开（公告）日：2005-02-10

  A compound of the formula (I) wherein Ring A and Ring B are: (1) Ring A is an optionally substituted unsaturated monocyclic heterocyclic ring, and Ring B is an optionally substituted unsaturated monocyclic heterocyclic ring, an optionally substituted unsaturated fused heterobicyclic ring, or an optionally substituted benzene ring, (2) Ring A is an optionally substituted benzene ring, and Ring B is an optionally substituted unsaturated monocyclic heterocyclic ring or an optionally substituted unsaturated fused heterobicyclic ring, or (3) Ring A is an optionally substituted unsaturated fused heterobicyclic ring, and Ring B are independently an optionally substituted unsaturated monocyclic heterocyclic ring, an optionally substituted unsaturated fused heterobicyclic ring, or an optionally substituted benzene ring; X is a carbon atom or a nitrogen atom; Y is -(CH2)n- (n is 1 or 2); a pharmaceutically acceptable salt thereof, or a prodrug thereof.

  化合物的式子（I）其中环A和环B为：（1）环A是可选取代的不饱和单环杂环，环B是可选取代的不饱和单环杂环、可选取代的不饱和融合杂双环或可选取代的苯环，（2）环A是可选取代的苯环，环B是可选取代的不饱和单环杂环或可选取代的不饱和融合杂双环，或（3）环A是可选取代的不饱和融合杂双环，环B独立地是可选取代的不饱和单环杂环、可选取代的不饱和融合杂双环或可选取代的苯环；X是碳原子或氮原子；Y是-(CH2)n-（n为1或2）；其药物可接受的盐或前药。
• Novel compounds
  申请人：Nomura Sumihiro

  公开号：US20050233988A1

  公开（公告）日：2005-10-20

  A compound of the formula: wherein Ring A and Ring B are: (1) Ring A is an optionally substituted unsaturated monocyclic heterocyclic ring, and Ring B is an optionally substituted unsaturated monocyclic heterocyclic ring, an optionally substituted unsaturated fused heterobicyclic ring, or an optionally substituted benzene ring, (2) Ring A is an optionally substituted benzene ring, and Ring B is an optionally substituted unsaturated monocyclic heterocyclic ring or an optionally substituted unsaturated fused heterobicyclic ring, or (3) Ring A is an optionally substituted unsaturated fused heterobicyclic ring, and Ring B are independently an optionally substituted unsaturated monocyclic heterocyclic ring, an optionally substituted unsaturated fused heterobicyclic ring, or an optionally substituted benzene ring; X is a carbon atom or a nitrogen atom; Y is —(CH 2 ) n — (n is 1 or 2); a pharmaceutically acceptable salt thereof, or a prodrug thereof.

  一种化合物，其化学式为：其中环A和环B分别为：（1）环A为可选取代的不饱和单环杂环，环B为可选取代的不饱和单环杂环、可选取代的不饱和融合杂双环或可选取代的苯环；（2）环A为可选取代的苯环，环B为可选取代的不饱和单环杂环或可选取代的不饱和融合杂双环；或（3）环A为可选取代的不饱和融合杂双环，环B独立地为可选取代的不饱和单环杂环、可选取代的不饱和融合杂双环或可选取代的苯环；X为碳原子或氮原子；Y为—（CH2）n—（n为1或2）；其药学上可接受的盐或其前药。
• GLUCOPYRANOSIDE COMPOUND
  申请人：NOMURA Sumihiro

  公开号：US20120258913A1

  公开（公告）日：2012-10-11

  A compound of the formula: wherein Ring A and Ring B are: (1) Ring A is an optionally substituted unsaturated monocyclic heterocyclic ring, and Ring B is an optionally substituted unsaturated monocyclic heterocyclic ring, an optionally substituted unsaturated fused heterobicyclic ring, or an optionally substituted benzene ring, (2) Ring A is an optionally substituted benzene ring, and Ring B is an optionally substituted unsaturated monocyclic heterocyclic ring or an optionally substituted unsaturated fused heterobicyclic ring, or (3) Ring A is an optionally substituted unsaturated fused heterobicyclic ring, and Ring B are independently an optionally substituted unsaturated monocyclic heterocyclic ring, an optionally substituted unsaturated fused heterobicyclic ring, or an optionally substituted benzene ring; X is a carbon atom or a nitrogen atom; Y is —(CH 2 ) n — (n is 1 or 2); or a pharmaceutically acceptable salt thereof, or a prodrug thereof.

  一种化合物的公式：其中环A和环B是：(1) 环A是一个可选取代的不饱和单环杂环，环B是一个可选取代的不饱和单环杂环、可选取代的不饱和融合杂双环或可选取代的苯环，(2) 环A是一个可选取代的苯环，环B是一个可选取代的不饱和单环杂环或可选取代的不饱和融合杂双环，或(3) 环A是一个可选取代的不饱和融合杂双环，环B是独立的可选取代的不饱和单环杂环、可选取代的不饱和融合杂双环或可选取代的苯环；X是一个碳原子或氮原子；Y是—(CH2)n—(n为1或2)；或其药学上可接受的盐或前药。
• Novel compounds having inhibitory activity against sodium-dependant glucose transporter
  申请人：Mitsubishi Tanabe Pharma Corporation

  公开号：EP2514756A1

  公开（公告）日：2012-10-24

  A compound of the formula: wherein Ring A and Ring B are: (1) Ring A is an optionally substituted unsaturated monocyclic heterocyclic ring, and Ring B is an optionally substituted unsaturated monocyclic heterocyclic ring, an optionally substituted unsaturated fused heterobicyclic ring, or an optionally substituted benzene ring, (2) Ring A is an optionally substituted benzene ring, and Ring B is an optionally substituted unsaturated monocyclic heterocyclic ring or an optionally substituted unsaturated fused heterobicyclic ring, or (3) Ring A is an optionally substituted unsaturated fused heterobicyclic ring, and Ring B are independently an optionally substituted unsaturated monocyclic heterocyclic ring, an optionally substituted unsaturated fused heterobicyclic ring, or an optionally substituted benzene ring; X is a carbon atom or a nitrogen atom; Y is ―(CH2)n-(n is 1 or 2); a pharmaceutically acceptable salt thereof, or a prodrug thereof.

  式中的化合物： 其中环 A 和环 B 是(1) 环 A 是被任选取代的不饱和单环杂环，环 B 是被任选取代的不饱和单环杂环、被任选取代的不饱和融合杂环或被任选取代的苯环环 B 是任选取代的不饱和单环杂环或任选取代的不饱和融合杂环，或 (3) 环 A 是任选取代的不饱和融合杂环，环 B 独立地是任选取代的不饱和单环杂环、任选取代的不饱和融合杂环或任选取代的苯环；X 是碳原子或氮原子； Y 是-(CH2)n-(n 是 1 或 2)； 其药学上可接受的盐，或其原药。
• NOVEL COMPOUNDS HAVING INHIBITORY ACTIVITY AGAINST SODIUM-DEPENDANT GLUCOSE TRANSPORTER
  申请人：Mitsubishi Tanabe Pharma Corporation

  公开号：EP3251679A1

  公开（公告）日：2017-12-06

  Use of a compound of formula (IA): wherein RA is a halogen atom, a lower alkyl group or a lower alkoxy group; RB is a phenyl group optionally substituted by a halogen atom, a cyano group, a lower alkyl group, a halo-lower alkyl group, a lower alkoxy group, a halo-lower alkoxy group, or a mono- or di-lower alkylamino group; or a heterocyclyl group optionally substituted by a halogen atom, a cyano group, a lower alkyl group, a halo-lower alkyl group, a lower alkoxy group, a halo-lower alkoxy group, or a mono- or di-lower alkylamino group; and Rc is hydrogen atom; or RB and RC taken together are a fused benzene ring which may be substituted by a halogen atom, a lower alkyl group, a halo-lower alkyl group, a lower alkoxy group or a halo-lower alkoxy group; in the manufacture of a medicament for the treatment of diabetes mellitus (type 1 and type 2), diabetic retinopathy, diabetic neuropathy, diabetic nephropathy, postprandial hyperglycemia, or delayed wound healing.

  使用式(IA)化合物： 其中 RA 是卤素原子、低级烷基或低级烷氧基；RB 是任选被卤素原子、氰基、低级烷基、卤代低级烷基、低级烷氧基、卤代低级烷氧基或单或双低级烷基氨基取代的苯基；或可被卤素原子、氰基、低级烷基、卤代低级烷基、低级烷氧基、卤代低级烷氧基或单低或双低烷基氨基取代的杂环基团；且 Rc 为氢原子；或 RB 和 RC 合在一起为可被卤素原子、低级烷基、卤代低级烷基、低级烷氧基或卤代低级烷氧基取代的融合苯环； 用于制造治疗糖尿病（1 型和 2 型）、糖尿病视网膜病变、糖尿病神经病 变、糖尿病肾病、餐后高血糖或伤口延迟愈合的药物。