3-氨基-5-(噻吩-3-基)噻吩-2-羧酸甲酯 | 175137-07-2

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 双噻吩和低聚噻吩
• 中文名称: 3-氨基-5-(噻吩-3-基)噻吩-2-羧酸甲酯
• 英文名称: methyl 3-amino-5-(3-thienyl)thiophene-2-carboxylate
• 英文别名: methyl 3-amino-5-thiophen-3-ylthiophene-2-carboxylate
• CAS: 175137-07-2
• 化学式: C₁₀H₉NO₂S₂
• 分子量: 239.319
• InChiKey: APQCWRRLXICQCG-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3
• 重原子数：
  15
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.1
• 拓扑面积：
  109
• 氢给体数：
  1
• 氢受体数：
  5

安全信息

• 海关编码：
  2934999090

反应信息

• 作为反应物：
  描述：

  3-氨基-5-(噻吩-3-基)噻吩-2-羧酸甲酯 在 sodium hydroxide 、 氯化亚砜 、 氨 作用下， 以 甲醇 、 乙腈 为溶剂， 生成 4-氨基-[2,3']联噻吩-5-甲酰胺
  参考文献：
  名称：

  Hit-to-lead studies: the discovery of potent, orally active, thiophenecarboxamide IKK-2 inhibitors

  摘要：

  A hit-to-lead optimisation programme was carried out on the thiophenecarboxamide high throughput screening hits 1 and 2 resulting in the discovery of the potent and orally bioavailable IKK-2 inhibitor 22. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2004.03.058
• 作为产物：
  描述：

  2-Propenenitrile, 3-chloro-3-(3-thienyl)- 、 巯基乙酸甲酯 在 sodium methylate 作用下， 以 甲醇 为溶剂， 反应 0.17h， 生成 3-氨基-5-(噻吩-3-基)噻吩-2-羧酸甲酯
  参考文献：
  名称：

  The discovery and optimization of pyrimidinone-containing MCH R1 antagonists

  摘要：

  Optimization of a series of constrained melanin-concentrating hormone receptor 1 (MCH RI) antagonists has provided compounds with potent and selective MCH R1 activity. Details of the optimization process are provided and the use of one of the compounds in an animal model of diet-induced obesity is presented. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2006.07.008

文献信息

• Synthesis and combinatorial approach of the reactivity of 6- and 7-arylthieno[3,2-d][1,3]oxazine-2,4-diones
  作者：François-Xavier Le Foulon、Emmanuelle Braud、Frédéric Fabis、Jean-Charles Lancelot、Sylvain Rault

  DOI：10.1016/j.tet.2003.10.028

  日期：2003.12

  This paper describes a general procedure for the synthesis of new substituted thiaisatoic anhydrides or 6- or 7-aryl-1H-thiéno[3,2-d][1,3]oxazine-2,4-diones 3a–j and 4a–f. They were synthesized in large scale under microwave heating conditions with high yields. The reactivity vs nucleophilic reagents of these compounds was studied and permitted to develop a simple combinatorial procedure to synthesize

  本文描述了合成新的取代硫代硫杂酸酐或6-或7-芳基-1 H-噻吩并[3,2- d ] [1,3]恶嗪-2,4-二酮3a – j和4a的一般程序。 – f。它们在微波加热条件下以高收率大规模合成。研究了这些化合物的亲核试剂的反应性与亲核试剂的关系，并允许开发一种简单的组合方法来合成新的噻吩脲酸7a – j和8a – j库。
• Synthesis, anti-HIV-1 integrase, and cytotoxic activities of 4-chloro-N-(4-oxopyrimidin-2-yl)-2-mercaptobenzenesulfonamide derivatives
  作者：Zdzisław Brzozowski、Jarosław Sławiński、Franciszek Sączewski、Tino Sanchez、Nouri Neamati

  DOI：10.1016/j.ejmech.2007.08.013

  日期：2008.6

  Several 4-chloro-N-(4-oxopyrimidin-2-yl)-2-mercaptobenzenesulfonamide derivatives 13-28 and 35-44 have been synthesized and tested as potential HIV-1 integrase (IN) inhibitors. Compounds 15-17, 19, 21-28, 36 and 41 inhibited IN with IC(50) values in the range of 3.3-63.0 microM. The compounds 13, 15, 16, 21-24 and 26-28 were further tested at the US National Cancer Institute for their in vitro activity

  几种4-氯-N-（4-氧嘧啶基-2-基）-2-巯基苯磺酰胺衍生物13-28和35-44已被合成并作为潜在的HIV-1整合酶（IN）抑制剂进行了测试。化合物15-17、19、21-28、36和41抑制IN的IC（50）值在3.3-63.0 microM之间。在美国国家癌症研究所进一步测试了化合物13、15、16、21-24和26-28的抗53-57种人类肿瘤细胞系的体外活性。化合物26-28是无活性的，而其他化合物对一种或多种人类肿瘤细胞系表现出高或合理的活性（GI（50）<0.01-20.0 microM）。
• [EN] CHK1 KINASE INHIBITORS<br/>[FR] INHIBITEURS DE KINASE CHK1
  申请人：SMITHKLINE BEECHAM CORP

  公开号：WO2003028731A1

  公开（公告）日：2003-04-10

  Novel compounds useful in the inhibition of damage response kinases are provided.

  提供了一种新型化合物，可用于抑制损伤反应激酶。
• Discovery and SAR of a Novel Selective and Orally Bioavailable Nonpeptide Classical Competitive Inhibitor Class of Protein-Tyrosine Phosphatase 1B
  作者：Henrik Sune Andersen、Ole H. Olsen、Lars F. Iversen、Anette L. P. Sørensen、Steen B. Mortensen、Michael S. Christensen、Sven Branner、Thomas K. Hansen、Jesper F. Lau、Lone Jeppesen、Edmond J. Moran、Jing Su、Farid Bakir、Luke Judge、Manou Shahbaz、Tassie Collins、Todd Vo、Michael J. Newman、William C. Ripka、Niels Peter H. Møller

  DOI：10.1021/jm0209026

  日期：2002.9.1

  Reversible phosphorylation and dephosphorylation of key proteins on tyrosine residues are important parts of intracellular signaling triggered by hormones and other agents. Recent knock-out studies in mice have identified PTP1B as a potential target for the treatment of diabetes and obesity. As a consequence, a number of academic and industrial groups are aggressively pursuing the development of selective PTP1B inhibitors. In addition, other protein-tyrosine phosphatases (PTPs) appear to be critically involved in major diseases such as cancer and autoimmunity. Given the diversity of PTPs and their potential as drug targets in different diseases, we have taken a broad approach to develop active site-directed selective inhibitors of specific members of this family of enzymes. Using a high throughput screening, we have previously identified 2-(oxalylamino)benzoic acid 3a as a relatively weak but classical competitive inhibitor of several PTPs.(4) On the basis of our early studies, indicating that 3a might be used as a starting point for the synthesis of selective PTP inhibitors, we now present our efforts in expansion of this concept and provide here a number of new chemical scaffolds for the development of inhibitors of different members of the PTP family. Although the core structure of these inhibitors is charged, good oral bioavailability has been observed in rat for some compounds. Furthermore, we have observed enhancement of 2-deoxy-glucose accumulation in C2C12 cells with prodrug analogues.