2-(benzo[d]thiazol-2-ylmethylthio)-6-ethoxybenzo[d]-thiazole | 452942-47-1

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并噻唑类
• 英文名称: 2-(benzo[d]thiazol-2-ylmethylthio)-6-ethoxybenzo[d]-thiazole
• 英文别名: 2-(benzothiazol-2-ylmethylsulfanyl)-6-ethoxy-benzothiazole；2-[(2-benzothiazolylmethyl)thio]-6-ethoxybenzothiazole；2-((Benzothiazol-2-ylmethyl)thio)-6-ethoxybenzothiazole；2-(1,3-benzothiazol-2-ylmethylsulfanyl)-6-ethoxy-1,3-benzothiazole
• CAS: 452942-47-1
• 化学式: C₁₇H₁₄N₂OS₃
• 分子量: 358.509
• InChiKey: DPBNRWJKKXKWRA-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.5
• 重原子数：
  23
• 可旋转键数：
  5
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.18
• 拓扑面积：
  117
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  2-氯甲基-1,3-苯并噻唑 在 sodium t-butanolate 、 potassium thioacetate 作用下， 以 甲苯 、 乙腈 为溶剂， 反应 13.0h， 生成 2-(benzo[d]thiazol-2-ylmethylthio)-6-ethoxybenzo[d]-thiazole
  参考文献：
  名称：

  一种2-[(2-苯并噻唑甲基)硫基]-6-乙氧基苯并噻唑及其中间体的制备方法

  摘要：

  本发明提供了一种2‑[(2‑苯并噻唑甲基)硫基]‑6‑乙氧基苯并噻唑的制备方法，包含以下步骤：碱性条件下，在无催化剂或催化剂存在条件下，化合物（）于一定溶剂中与化合物（）反应，得到化合物（），即2‑[(2‑苯并噻唑甲基)硫基]‑6‑乙氧基苯并噻唑；本发明还提供了一种制备化合物（）的方法，包含以下步骤：化合物（）于一定溶剂中依次与亚硝化试剂和铜试剂反应；同时，本发明还提供了一种制备化合物（）的方法，包含以下步骤：化合物（）于一定溶剂中与硫化试剂反应得到化合物（III）。本发明的原辅料廉价易得或易于制备；反应条件温和，选择性好，收率高；本发明通过结晶纯化中间体和产品，避免柱层析，适合工业化。

  公开号：

  CN108774194A

文献信息

• COMPOUNDS AND COMPOSITIONS FOR USE IN AUGMENTATION OF GLUCOSE
  申请人：Sasson Shlomo

  公开号：US20150025094A1

  公开（公告）日：2015-01-22

  The present invention is directed to compounds such as: formula wherein linker is independently selected from the group consisting of —S—, —S—S—, —S—(CH2)n—, —NH—, —NH—(CH2)n—, —O—, —S02-, arylene, heteroarylene; R1 is selected from the group consisting of straight or branched C4-C20 alkyl, straight or branched C4-C20 alkenyl, straight or branched C4-C20 alkynyl, each optionally interrupted with at least one NH, C5-C7 saturated cycloalkyl or heteroalkyl ring, C5-C12 aromatic or heteroaromatic ring, each optionally substituted with at least one group selected from —COOH, —NH2, C1-C8 alkoxy, C1-C5 amidyle, C1-C5 carboxyl, halogen; and R2 is independently selected from the group consisting of H, OH, SH, NH2, NO2, halogen, CN, C1-C8 alkoxy, C1-C5 carboxylic acid, straight or branched C1-C8 alkyl, straight or branched C2-C10 alkenyl, straight or branched C2-C12 alkynyl each optionally substituted by at least one substituent selected from the group consisting of C1-C5 alkoxy, C1-C5 carboxylic acid, OH, SH, NH2, halogen; and compositions for use in the treatment of diabetes and related dis orders.

  本发明涉及化合物，例如：式中，连接体独立地选自由以下组成的群组：—S—、—S—S—、—S—(CH2)n—、—NH—、—NH—(CH2)n—、—O—、—S02-、芳基和杂环芳基；R1选自由以下组成的群组：直链或支链的C4-C20烷基、直链或支链的C4-C20烯基、直链或支链的C4-C20炔基，每个选项均可中断至少一个NH、C5-C7饱和环烷基或杂基环、C5-C12芳香或杂环芳香环，每个选项均可用至少一种从—COOH、—NH2、C1-C8烷氧基、C1-C5酰胺基、C1-C5羧基和卤素中选取的基团进行取代；R2独立地选自由以下组成的群组：H、OH、SH、NH2、NO2、卤素、CN、C1-C8烷氧基、C1-C5羧酸、直链或支链的C1-C8烷基、直链或支链的C2-C10烯基、直链或支链的C2-C12炔基，每个选项均可用至少一种从C1-C5烷氧基、C1-C5羧酸、OH、SH、NH2和卤素中选取的取代基团进行取代；以及用于治疗糖尿病及相关疾病的组合物。
• Compounds and compositions for use in augmentation of glucose
  申请人：Sasson Shlomo

  公开号：US09409904B2

  公开（公告）日：2016-08-09

  The present invention is directed to compounds such as: formula wherein linker is independently selected from the group consisting of —S—, —S—S—, —S—(CH2)n-, —NH—, —NH—(CH2)n-, —O—, —SO2-, arylene, heteroarylene; R1 is selected from the group consisting of straight or branched C4-C20 alkyl, straight or branched C4-C20 alkenyl, straight or branched C4-C20 alkynyl, each optionally interrupted with at least one NH, C5-C7 saturated cycloalkyl or heteroalkyl ring, C5-C12 aromatic or heteroaromatic ring, each optionally substituted with at least one group selected from —COOH, —NH2, C1-C8 alkoxy, C1-C5 amidyle, C1-C5 carboxyl, halogen; and R2 is independently selected from the group consisting of H, OH, SH, NH2, NO2, halogen, CN, C1-C8 alkoxy, C1-C5 carboxylic acid, straight or branched C1-C8 alkyl, straight or branched C2-C10 alkenyl, straight or branched C2-C12 alkynyl each optionally substituted by at least one substituent selected from the group consisting of C1-C5 alkoxy, C1-C5 carboxylic acid, OH, SH, NH2, halogen; and compositions for use in the treatment of diabetes and related disorders.

  本发明涉及化合物，例如：式中，连接基独立选择自羟基、硫醚基、二硫醚基、硫代烷基、氮醚基、氮代烷基、氧代烷基、磺酰基、芳基、杂芳基等组成的群体中；R1选择自直链或支链C4-C20烷基、直链或支链C4-C20烯基、直链或支链C4-C20炔基，每个都可以被至少一个NH打断，C5-C7饱和环烷基或杂基环、C5-C12芳香或杂芳环，每个都可以被至少一个羧基（—COOH）、氨基（—NH2）、C1-C8烷氧基、C1-C5酰胺基、C1-C5羧基、卤素等中的至少一种基团取代；R2独立选择自H、OH、SH、NH2、NO2、卤素、CN、C1-C8烷氧基、C1-C5羧酸、直链或支链C1-C8烷基、直链或支链C2-C10烯基、直链或支链C2-C12炔基，每个都可以被至少一个羟基（OH）、硫醇基（SH）、氨基（NH2）、卤素等中的至少一种基团取代；以及用于治疗糖尿病和相关疾病的组合物。
• [EN] COMPOUNDS AND COMPOSITIONS FOR USE IN AUGMENTATION OF GLUCOSE UPTAKE AND INSULIN SECRETION<br/>[FR] COMPOSÉS ET COMPOSITIONS POUR UNE UTILISATION DANS L'AUGMENTATION DE L'ABSORPTION DU GLUCOSE ET DE LA SÉCRÉTION D'INSULINE
  申请人：YISSUM RES DEV CO

  公开号：WO2013018095A8

  公开（公告）日：2013-12-27
• Synthesis and Mechanism of Hypoglycemic Activity of Benzothiazole Derivatives
  作者：Ella Meltzer-Mats、Gali Babai-Shani、Lily Pasternak、Neta Uritsky、Tamar Getter、Olga Viskind、Jürgen Eckel、Erol Cerasi、Hanoch Senderowitz、Shlomo Sasson、Arie Gruzman

  DOI：10.1021/jm4001488

  日期：2013.7.11

  Adenosine 5'-monophosphate activated protein kinase (AMPK) has emerged as a major potential target for novel antidiabetic drugs. We studied the structure of 2-chloro-5-((Z)-((E)-5-((5-(4,5-dimethyl-2-nitrophenyl)furan-2-yl)methylene)-4-oxothiazolidin-2-ylidene)amino)benzoic acid (PT-1), which attenuates the autoinhibition of the enzyme AMPK, for the design and synthesis of different benzothiazoles with potential antidiabetic activity. We synthesized several structurally related benzothiazole derivatives that increased the rate of glucose uptake in L6 myotubes in an AMPK-dependent manner. One compound, 2-(benzo[d]thiazol-2-ylmethylthio)-6-ethoxybenzo[d]thiazole (34), augmented the rate of glucose uptake up to 2.5-fold compared with vehicle-treated cells and up to 1.1-fold compared to PT-1. Concomitantly, it elevated the abundance of GLUT4 in the plasma membrane of the myotubes and activated AMPK. Subcutaneous administration of 34 to hyperglycemic Kuo Kondo rats carrying the Ay-yellow obese gene (KKAy) mice lowered blood glucose levels toward the normoglycemic range. In accord with its activity, compound 34 showed a high fit value to a pharmacophore model derived from the PT-1.
• COMPOUNDS AND COMPOSITIONS FOR USE IN AUGMENTATION OF GLUCOSE UPTAKE AND INSULIN SECRETION
  申请人：Yissum Research Development Company of The Hebrew University of Jerusalem Ltd.

  公开号：EP2739612A1

  公开（公告）日：2014-06-11