2-amino-5-(4-methyl-4H-(1,2,4)-triazole-3-yl)sulfanyl-N-(4-methylthiazole-2-yl)benzamide

• 分子结构分类: 有机化合物 - 有机硫化合物 - 硫醚类
• 英文名称: 2-amino-5-(4-methyl-4H-(1,2,4)-triazole-3-yl)sulfanyl-N-(4-methylthiazole-2-yl)benzamide
• 英文别名: 2-amino-N-(4-methyl-1,3-thiazol-2-yl)-5-[(4-methyl-4H-1,2,4-triazol-3-yl)sulfanyl]benzamide；2-amino-5-(4-methyl-4H-[1,2,4]triazol-3-ylsulfanyl)-N-(4-methylthiazol-2-yl)benzamide；2-amino-N-(4-methyl-1,3-thiazol-2-yl)-5-[(4-methyl-1,2,4-triazol-3-yl)sulfanyl]benzamide
• 化学式: C₁₄H₁₄N₆OS₂
• 分子量: 346.437
• InChiKey: JEBOJMQHVUEKBE-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  23
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.14
• 拓扑面积：
  152
• 氢给体数：
  2
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  2-amino-5-(4-methyl-4H-(1,2,4)-triazole-3-yl)sulfanyl-N-(4-methylthiazole-2-yl)benzamide 在 硫酸 、 溶剂黄146 、 sodium nitrite 、 copper(I) oxide 作用下， 以 乙醇 为溶剂， 反应 0.83h， 以24%的产率得到N-(4-methyl-1,3-thiazol-2-yl)-3-[(4-methyl-4H-1,2,4-triazol-3-yl)sulfanyl]benzamide
  参考文献：
  名称：

  Discovery of potent and orally active 3-alkoxy-5-phenoxy-N-thiazolyl benzamides as novel allosteric glucokinase activators

  摘要：

  Identification and synthesis of novel 3-alkoxy-5-phenoxy-N-thiazolyl benzamides as glucokinase activators are described. Removal of an aniline structure of the prototype lead (2a) and incorporation of an alkoxy or phenoxy substituent led to the identification of 3-Isopropoxy-5-[4-(methylsulfonyl) phenoxy]-N(4- methyl-1,3-thiazol-2-yl) benzamide (27e) as a novel, potent, and orally bioavailable GK activator. Rat oral glucose tolerance test indicated that 27e exhibited a glucose-lowering effect after 10 mg/kg oral administration. (c) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2009.02.038
• 作为产物：
  描述：

  5-(4-methyl-4H-1,2,4-triazol-3-ylthio)-N-(4-methylthiazol-2-yl)-2-nitrobenzamide 在 铁粉 、 氯化铵 作用下， 以 水 、 异丙醇 为溶剂， 生成 2-amino-5-(4-methyl-4H-(1,2,4)-triazole-3-yl)sulfanyl-N-(4-methylthiazole-2-yl)benzamide
  参考文献：
  名称：

  Identification of novel and potent 2-amino benzamide derivatives as allosteric glucokinase activators

  摘要：

  The identification and structure-activity-relationships (SARs) of novel 2-amino benzamide glucokinase activators are described. Compounds in this series were developed to be potent GK activators, and their binding mode to the GK protein was determined by crystal structure analysis. In vivo pharmacokinetic and acute in vivo efficacy studies of compound 18 are also described.

  DOI：

  10.1016/j.bmcl.2009.01.053

文献信息

• Novel aminobenzamide derivative
  申请人：Nishimura Teruyuki

  公开号：US20050282815A1

  公开（公告）日：2005-12-22

  This invention relates to a novel compound represented by the formula (I): or a pharmaceutically acceptable salt thereof, wherein R 1 is —S(O)p-A, —S—(O)q-B or —O-D, wherein p and q, which are the same or different, each represent an integer from 0 to 2, A is a straight chain C1-C10 alkyl group which may be substituted by R 10 , and B and D each independently represent R 12 which may be substituted by R 10 ; R 2 is a hydrogen atom, a halogen atom, or a straight chain or branched C1-C6 alkyl group which may be substituted by R 10 ; X 1 and X 2 each independently represent N or CH, but cannot both be N; the formula (II): shows a monocyclic or bicyclic heteroaryl group which has a nitrogen atom adjacent to the carbon atom bonded to the amide group, and the heteroaryl group may be substituted by R 10 ; R 10 is R 11 , or a hydrocarbon group which may be substituted by R 11 ; R 11 is, for example, a hydrogen atom or amino; and R 12 is, for example, phenyl, thiazolyl, pyridyl or methylene dioxyphenyl. The compound according to this invention has a glucokinase activation effect, and for example, is useful in the treatment and prevention of diabetes mellitus, and in the prevention of its complications such as diabetic nephropathy, diabetic retinopathy, diabetic neuropathy and diabetic arteriosclerosis.

  本发明涉及一种由式（I）代表的新型化合物： 或其药学上可接受的盐，其中 R 1 是-S(O)p-A、-S-(O)q-B 或-O-D，其中 p 和 q 相同或不同，各代表 0 至 2 的整数，A 是可被 R 取代的直链 C1-C10 烷基 10 B 和 D 各自独立地代表 R 12 可被 R 10 ; R 2 是氢原子、卤素原子或直链或支链 C1-C6 烷基，可被 R 10 ; X 1 和 X 2 各自独立地代表 N 或 CH，但不能都是 N； 式 (II)： 表示一个单环或双环杂芳基，该杂芳基具有一个与酰胺基键合的碳原子相邻的氮原子，该杂芳基可被 R 10 ; R 10 是 R 11 或可被 R 11 取代的烃基 11 ; R 11 例如是氢原子或氨基；以及 R 12 例如是苯基、噻唑基、吡啶基或亚甲基二氧苯基。根据本发明的化合物具有葡萄糖激酶活化作用，例如，可用于治疗和预防糖尿病，以及预防其并发症，如糖尿病肾病、糖尿病视网膜病变、糖尿病神经病变和糖尿病动脉硬化。
• NOVEL AMINOBENZAMIDE DERIVATIVE
  申请人：BANYU PHARMACEUTICAL CO., LTD.

  公开号：EP1496052B1

  公开（公告）日：2009-08-05
• REGULATED BIOCIRCUIT SYSTEMS
  申请人：Obsidian Therapeutics, Inc.

  公开号：US20190192691A1

  公开（公告）日：2019-06-27

  The present invention provides regulatable biocircuit systems. Such systems provide modular and tunable protein expression systems in support of the discovery and development of therapeutic modalities.
• IDENTIFICATION AND TARGETED MODULATION OF GENE SIGNALING NETWORKS
  申请人：CAMP4 THERAPEUTICS CORPORATION

  公开号：US20210254056A1

  公开（公告）日：2021-08-19

  The present invention provides methods and compositions for the evaluation, alteration and/or optimization of gene signaling. Methods and systems are also provided which exploit the information generated in the identification of new targets and non-canonical signaling pathways.
• US7253188B2
  申请人：——

  公开号：US7253188B2

  公开（公告）日：2007-08-07