2,3-二氨基苯甲酸乙酯 | 37466-88-9

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 中文名称: 2,3-二氨基苯甲酸乙酯
• 英文名称: ethyl 2,3-diaminobenzoate
• 英文别名: 2,3-Diaminobenzoic acid,ethyl ester
• CAS: 37466-88-9
• 化学式: C₉H₁₂N₂O₂
• 分子量: 180.206
• InChiKey: SBNFMGRCKKFSLR-UHFFFAOYSA-N

物化性质

• 沸点：
  333.6±22.0 °C(Predicted)
• 密度：
  1.214±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.9
• 重原子数：
  13
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.22
• 拓扑面积：
  78.3
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  2,3-二氨基苯甲酸乙酯 在 吡啶 、 盐酸 作用下， 以 二氯甲烷 、 水 为溶剂， 反应 21.0h， 生成 ethyl 3-[(4-methoxybenzoyl)amino]-2-{[4-(4-methyl-1,4-diazepan-1-yl)benzoyl]amino}benzoate hydrochloride
  参考文献：
  名称：

  Discovery of N-[2-Hydroxy-6-(4-methoxybenzamido)phenyl]-4- (4-methyl-1,4-diazepan-1-yl)benzamide (Darexaban, YM150) as a Potent and Orally Available Factor Xa Inhibitor

  摘要：

  Inhibitors of factor Xa (FXa), a crucial serine protease in the coagulation cascade, have attracted a great deal of attention as a target for developing antithrombotic agents. We previously reported findings from our optimization study of a high-throughput screening (HTS) derived lead compound la that resulted in the discovery of potent amidine-containing FXa inhibitors represented by compound 2. We also conducted an alternative optimization study of la without incorporating a strong basic amidine group, which generally has an adverse effect on the pharmacokinetic profile after oral administration. Replacement of 4-methoxybenzene with a 1,4-benzodiazepine structure and introduction of a hydroxy group at the central benzene led to the discovery of the potent and orally effective factor Xa inhibitor 14i (darexaban, YM150). Subsequent extensive study revealed a unique aspect to the pharmacokinetic profile of this compound, wherein the hydroxy moiety of 141 is rapidly transformed into its glucuronide conjugate 16 (YM-222714) as an active metabolite after oral administration and it plays a major role in expression of potent anticoagulant activity in plasma. The distinctive, potent activity of inhibitor 14i after oral dosing was explained by this unique pharmacokinetic profile and its favorable membrane permeability. Compound 14i is currently undergoing clinical development for prevention and treatment of thromboembolic diseases.

  DOI：

  10.1021/jm200868m
• 作为产物：
  描述：

  2-氨基-3-硝基苯甲酸乙酯 在 palladium 10% on activated carbon 氢气 作用下， 以 乙醇 为溶剂， 生成 2,3-二氨基苯甲酸乙酯
  参考文献：
  名称：

  Cyclo-alkyl substituted benzimidazoles and their use as PARP inhibitors

  摘要：

  公式I或II及其互变异构形式、可能的对映体和非对映异构体形式、环A上可能的顺式异构体以及这些化合物的前药，含有这些化合物的药物组合物以及使用这些化合物治疗神经退行性疾病或神经损伤的方法。

  公开号：

  US06737421B1

文献信息

• Nicotinamide derivatives useful as PDE4 inhibitors
  申请人：Mathias Paul John

  公开号：US20050020626A1

  公开（公告）日：2005-01-27

  This invention relates to nicotinamide derivatives of general formula (I): in which R 1 , R 2 and R 3 have the meanings defined herein, and to processes for the preparation of, intermediates used in the preparation of, compositions containing and the uses of such derivatives.

  这项发明涉及一般式（I）的烟酰胺衍生物： 其中R1、R2和R3具有本文中定义的含义，并且涉及用于制备、用于制备的中间体、含有这种衍生物的组合物以及这种衍生物的用途的过程。
• Benzamide derivatives having a vasopressin antagonistic activity
  申请人：Fujisawa Pharmaceutical Co., Ltd.

  公开号：US06207693B1

  公开（公告）日：2001-03-27

  This invention relates to new benzamide derivatives having a vasopressin antagonistic activity, etc. and represented by general formula (I): wherein R1 is aryl optionally substituted with lower alkoxy, etc., R2 is lower alkyl, etc., R3 is hydrogen, etc., A is NH, etc., E is etc., X is —CH═CH—, —CH═N—, or S, and Y is a condensed heterocyclic group, etc., and pharmaceutically acceptable salts thereof, to processes for preparation thereof and to a pharmaceutical composition comprising the same.

  这项发明涉及新的苯甲酰胺衍生物，它们具有抗血管加压素活性，并由通式（I）表示： 其中R1是可选地被低级烷氧基取代的芳基等， R2是低级烷基等， R3是氢等， A是NH等， E是 等， X是—CH═CH—，—CH═N—或S，而 Y是稠合杂环基等， 以及它们的药用可接受盐，其制备过程以及包含它们的药物组合物。
• Compounds
  申请人：Barber Gordon Christopher

  公开号：US20050020611A1

  公开（公告）日：2005-01-27

  This invention relates to nicotinamide derivatives of general formula (I): in which R 1 , Z and R 2 have the meanings defined herein, and to processes for the preparation of, intermediates used in the preparation of, compositions containing and the uses of such derivatives.

  这项发明涉及一般式(I)的烟酰胺衍生物： 其中R1、Z和R2具有本文所定义的含义，并涉及用于制备、用于制备的中间体、含有和使用这种衍生物的组合物的过程。
• Discovery of simplified benzazole fragments derived from the marine benzosceptrin B as necroptosis inhibitors involving the receptor interacting protein Kinase-1
  作者：Mohamed Benchekroun、Ludmila Ermolenko、Minh Quan Tran、Agathe Vagneux、Hristo Nedev、Claire Delehouzé、Mohamed Souab、Blandine Baratte、Béatrice Josselin、Bogdan I. Iorga、Sandrine Ruchaud、Stéphane Bach、Ali Al-Mourabit

  DOI：10.1016/j.ejmech.2020.112337

  日期：2020.9

  tools based on simplified natural metabolites to help deciphering the molecular mechanism of necroptosis, simplified benzazole fragments including 2-aminobenzimidazole and the 2-aminobenzothiazole analogs were prepared during the synthesis of the marine benzosceptrin B. Conpounds inhibiting the RIPK1 protein kinase were discovered. A library of 54 synthetic analogues were prepared and evaluated through

  为了开发基于简化的天然代谢产物的新化学工具以帮助破译坏死病的分子机制，在海洋苯并缩合受体B的合成过程中制备了包括2-氨基苯并咪唑和2-氨基苯并噻唑类似物的简化苯并唑片段。抑制RIPK1的化合物蛋白激酶被发现。制备了54种合成类似物的文库，并通过表型筛选评估了FADD蛋白缺陷的人Jurkat T细胞中由TNF-α诱导的坏死性细胞死亡。本文报道了一系列2-氨基苯并唑类化合物通过抑制RIPK1蛋白激酶对坏死性细胞死亡的设计，合成和生物学评估。
• Heterocyclically substituted benzimidazoles, the production and application thereof
  申请人：Abbott GmbH & Co. KG

  公开号：US06696437B1

  公开（公告）日：2004-02-24

  The present invention relates to novel benzimidazoles, their preparation and their use as inhibitors of the enzyme poly(ADP-ribose) polymerase or PARP (EC 2.4.2.30) for producing drugs.

  本发明涉及新型苯并咪唑类化合物，其制备以及作为酶聚(ADP-核糖)聚合酶或PARP（EC 2.4.2.30）的抑制剂用于药物生产。