甲基3-乙酰氨基-5-硝基-2-噻吩羧酸酯 | 80615-54-9

• 分子结构分类: 有机化合物 - 有机氮化合物
• 中文名称: 甲基3-乙酰氨基-5-硝基-2-噻吩羧酸酯
• 英文名称: 2-carbomethoxy-3-acetamido-5-nitro-thiophene
• 英文别名: methyl 3-acetamido-5-nitrothiophene-2-carboxylate
• CAS: 80615-54-9
• 化学式: C₈H₈N₂O₅S
• 分子量: 244.228
• InChiKey: DJPJTIGJPWASOS-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.7
• 重原子数：
  16
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  130
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  甲基3-乙酰氨基-5-硝基-2-噻吩羧酸酯 在 盐酸 、 sodium methylate 、 铁粉 、 溶剂黄146 作用下， 以 甲醇 、 乙醇 、 氯仿 为溶剂， 生成 N-(2,4-Dioxo-1,2,3,4-tetrahydro-thieno[3,2-d]pyrimidin-6-yl)-guanidine; compound with acetic acid
  参考文献：
  名称：

  Design of novel N-(2,4-dioxo-1,2,3,4-tetrahydro-thieno[3,2-d]pyrimidin-7-yl)-guanidines as thymidine phosphorylase inhibitors, and flexible docking to a homology model

  摘要：

  A novel class of thymidine phosphorylase (TP) inhibitors has been designed based on analogy to the enzyme substrate as well as known inhibitors. Flexible docking studies, using a homology model of human TP, of the designed N-(2,4-dioxo-1,2,3,4-tetrahydro-thieno[3,2-d]pyrimidin-7-yl)-guanidines as well as their synthetic precursors provide insight into the observed experimental trends in binding affinity. (C) 2002 Published by Elsevier Science Ltd.

  DOI：

  10.1016/s0960-894x(02)00828-4
• 作为产物：
  描述：

  3-(乙酰基氨基)-2-噻吩羧酸甲酯 在 硫酸 、 硝酸 作用下， 以38%的产率得到甲基3-乙酰氨基-5-硝基-2-噻吩羧酸酯
  参考文献：
  名称：

  Potent selective thienoxazinone inhibitors of herpes proteases

  摘要：

  Thieno[3,2-d]oxazinones are potent selective, mechanism-based inhibitors of the herpes proteases with good aqueous stability. Specificity between the HSV and CMV proteases varies across the series: compounds 14b and 14c are submicromolar HSV protease inhibitors with modest CMV protease inhibition, 14g is a selective CMV protease inhibitor, and 32 inhibits both enzymes with an IC50 of about 1 mu M. (C) 1997 Elsevier Science Ltd.

  DOI：

  10.1016/s0960-894x(97)00300-4

文献信息

• Antihypertensive thienopyridines
  申请人：The Boots Company PLC

  公开号：US04710506A1

  公开（公告）日：1987-12-01

  Novel thienopyridones with antihypertensive activity have the formula I, ##STR1## wherein the ring A represents an optionally substituted thiophene ring; m is 0 or 1; n is 0, 1 or 2; R is lower alkyl and R.sub.1 is lower alkyl. The fused thieno-ring may carry one or two substituents. Formula I encompasses thieno[3,2-b]pyridones, thieno[3,4-b]pyridones and thieno[2,3-b]pyridones. Processes for preparing the novel thienopyridones and pharmaceutical compositions containing them are described. Pharmaceutically acceptable acid addition salts of the compounds of formula I are also described. The thienopyridones of formula I are antihypertensive agents and are also indicated for use in treating heart failure and ischaemic heart disease.

  新型具有降压活性的噻吩吡啶酮具有以下式I，其中环A代表可选择地取代的噻吩环；m为0或1；n为0、1或2；R为低碳基，R.sub.1为低碳基。融合的噻吩环可以携带一个或两个取代基。式I包括噻吩[3,2-b]吡啶酮，噻吩[3,4-b]吡啶酮和噻吩[2,3-b]吡啶酮。描述了制备新型噻吩吡啶酮和含有它们的药物组合物的方法。还描述了式I化合物的药用可接受的酸盐。式I的噻吩吡啶酮是降压剂，也适用于治疗心力衰竭和缺血性心脏病。
• The preparation of 2-(heterocyclyl)thikno[3,2-b]pyridine derivatives
  作者：Richard L. Elliott、Peter J. O'hanlon、Norman H. Rogers

  DOI：10.1016/s0040-4020(01)90298-4

  日期：1987.1

  The preparation of a series of 2-(heterocyclyl)-4-ethyl-4,7-dihydro -7-oxothieno[3,2-b]pyridine-6-carboxylic acids (5j-1) by aminolysis of the corresponding 2-bromo derivative (5i) is described. None of the compounds (5j-1) showed any interesting antibacterial activity.

  通过相应的2-氨基分解反应制备一系列2-（杂环基）-4-乙基-4,7-二氢-7-氧噻吩并[3,2-b]吡啶-6-羧酸（5j-1）描述了溴衍生物（5i）。化合物（5j-1）均未显示出任何令人感兴趣的抗菌活性。
• Distamycin-NA: A DNA Analog with an Aromatic Heterocyclic Polyamide Backbone. Part 1. Synthesis and structural analysis of monomers and dimers containing the nucleobase uracil
  作者：Guido Sauter、Eugen Stulz、Christian Leumann

  DOI：10.1002/hlca.19980810103

  日期：1998.1.12

  The synthesis of the monomeric building block 13 and its constitutional isomer 12 of a new type of DNA analog, distamycin-NA, is presented (Schemes 1 and 2). This building block consists of a uracil base attached to a thiophene core unit via a biaryl-like axis. Next to the biaryl-like axis on the thiophene chromophore, a carboxy and an amino substituent are located allowing for oligomerization via

  提出了新型的DNA类似物，双霉素-NA的单体结构单元13及其组成异构体12的合成（方案1和2）。该结构单元由尿嘧啶碱基组成，该碱基通过联芳基样轴与噻吩核心单元相连。在噻吩发色团上的联芳基样轴的旁边，有一个羧基和一个氨基取代基，可通过肽偶联进行低聚。通过对相应的硝基衍生物10和11进行X射线分析，建立了围绕联芳基样轴的结构证据和构象偏好。。因此，尿嘧啶碱基相对于噻吩核是螺旋式扭曲的，并且在晶体中的两个尿嘧啶碱基之间发生了二齿H键。使用分别在THF / LiCl和DMF中的二环己基碳二亚胺（DCC），将两个氨基酸结构单元12和13偶联以得到二聚体15和16。尽管二聚体15在室温下在NMR时间尺度上没有显示出对映异构性，但是由于绕其联芳基样轴的旋转受阻，其异构体16以不同的非对映异构体的形式出现。可变温度1 H-NMR实验可确定16 16 ±1 kcal / mol的旋转势垒。实验数据通过AM1计算得到补充。
• Thienopyridones, processes and intermediates for their preparation and pharmaceutical compositions containing them
  申请人：The Boots Company PLC

  公开号：EP0209977A2

  公开（公告）日：1987-01-28

  Novel thienopyridones with antihypertensive activity have the formula 1, wherein the ring A represents an optionally substituted thiophene ring; m is 0 or 1; n is 0,1 or 2; R is lower alkyl and R1 is lower alkyl. The fused thieno-ring may carry one or two substituents. Formula I encompasses thieno [3,2-b]pyridones. thieno[3,4-b]pyridones and thieno [2.3-b]pyridones. Processes for preparing the novel thienopyridones and pharmaceutical compositions containing them are described. Pharmaceutically acceptable acid addition salts of the compounds of formula I are also described. The thienopyridones of formula I are antihypertensive agents and are also indicated for use in treating heart failure and ischaemic heart disease.

  具有抗高血压活性的新型噻吩并吡啶酮具有式 1、 其中环 A 代表任选取代的噻吩环；m 为 0 或 1；n 为 0、1 或 2；R 为低级烷基，R1 为低级烷基。 融合的噻吩环可以带有一个或两个取代基。 式 I 包括噻吩并[3,2-b]吡啶酮、噻吩并[3,4-b]吡啶酮和噻吩并[2.3-b]吡啶酮。 本文描述了制备新型噻吩并吡啶酮及其药物组合物的工艺。还描述了式 I 化合物的药学上可接受的酸加成盐。 式 I 的噻吩并吡啶酮类化合物是抗高血压药物，也可用于治疗心力衰竭和缺血性心脏病。
• p38 Kinase inhibitors for the treatment of arthritis and osteoporosis: thienyl, furyl, and pyrrolyl ureas
  作者：Anikó M Redman、Jeffrey S Johnson、Robert Dally、Steve Swartz、Hanno Wild、Holger Paulsen、Yolanda Caringal、David Gunn、Joel Renick、Martin Osterhout、Jill Kingery-Wood、Roger A Smith、Wendy Lee、Jacques Dumas、Scott M Wilhelm、Timothy J Housley、Ajay Bhargava、Gerald E Ranges、Alka Shrikhande、Deborah Young、Michael Bombara、William J Scott

  DOI：10.1016/s0960-894x(00)00574-6

  日期：2001.1

  Inhibitors of the MAP kinase p38 are potentially useful for the treatment for osteoporosis, arthritis, and other inflammatory diseases. A series of thienyl, furyl, and pyrrolyl ureas has been identified as potent p38 inhibitors, displaying in vitro activity in the nanomolar range. (C) 2000 Elsevier Science Ltd. All rights reserved.