5-bromo-N-[(E)-(dimethylamino)methylidene]thiophene-2-sulfonamide | 900814-14-4

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 噻吩类
• 英文名称: 5-bromo-N-[(E)-(dimethylamino)methylidene]thiophene-2-sulfonamide
• 英文别名: 5-bromo-N-[(1E)-(dimethylamino)methylene]-thiophene-2-sulfonamide；N,N-dimethyl-N'-(5-bromothiophene-2-sulfonyl)formamidine；N'-(5-bromothiophen-2-yl)sulfonyl-N,N-dimethylmethanimidamide
• CAS: 900814-14-4
• 化学式: C₇H₉BrN₂O₂S₂
• 分子量: 297.197
• InChiKey: SQXPQOHYLPTCHJ-WEVVVXLNSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.2
• 重原子数：
  14
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  86.4
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  5-bromo-N-[(E)-(dimethylamino)methylidene]thiophene-2-sulfonamide 生成 5-(3-hydroxypropylthio)thiophene-2-sulfonamide
  参考文献：
  名称：

  SHEPARD, KENNETH L.;GRAHAM, SAMUEL L.

  摘要：

  DOI：
• 作为产物：
  描述：

  5-溴噻吩-2-磺酰胺 、 N,N-二甲基甲酰胺二甲基缩醛 以 水 、 乙腈 为溶剂， 生成 5-bromo-N-[(E)-(dimethylamino)methylidene]thiophene-2-sulfonamide
  参考文献：
  名称：

  Substituted thiophene-2-sulfonamide antiglaucoma agents

  摘要：

  硫代噻吩-2-磺胺酰胺具有5-烷基-S(O).sub.n-取代基，是治疗眼内压升高的碳酸酐酶抑制剂。

  公开号：

  US04721794A1

文献信息

• [EN] SUBSTITUTED ARYLCYCLOPROPYLACETAMIDES AS GLUCOKINASE ACTIVATORS<br/>[FR] ARYLCYCLOPROPYLACETAMIDES SUBSTITUES SERVANT D'ACTIVATEURS DE GLUCOKINASE
  申请人：LILLY CO ELI

  公开号：WO2004063179A1

  公开（公告）日：2004-07-29

  According to the present invention there is provided a compounds of formula (I): and pharmaceutically acceptable salts thereof.

  根据本发明提供了以下式(I)的化合物及其药用可接受的盐。
• [EN] HETEROARYL COMPOUNDS<br/>[FR] COMPOSES HETEROARYLE
  申请人：LILLY CO ELI

  公开号：WO2004063194A1

  公开（公告）日：2004-07-29

  According to the present invention there is provided a compound of formula (I) wherein Z isR3 is lower alkyl or halo lower alkyl having from 2 to 6 carbon atoms or arylalkyl or -(CH2)s-V where V is a 3 to 8-membered ring which is cycloalkyl, cycloalkenyl, or heterocycloalkyl having one heteroatom selected from oxygen and sulfur ; s is independently 0, 1 or 2; M is hydrogen or halo or lower alkyl or perfluoro-lower alkyl;A is or where Y is oxygen or sulfur, and its pharmaceutically acceptable salts thereof. These compounds are considered to be useful for the treatment of type II Diabetes.

  根据本发明提供了一个化合物的公式(I)，其中Z是R3是具有2至6个碳原子的较低烷基或卤代较低烷基或芳基烷基或-(CH2)s-V，其中V是一个3至8元环，该环是环烷基、环烯基或含有氧和硫的杂环烷基中选择的一个杂原子；s独立地为0、1或2；M是氢或卤素或较低烷基或全氟较低烷基；A是或其中Y是氧或硫，并且其在药学上可接受的盐。这些化合物被认为对治疗II型糖尿病有用。
• Substituted arylcyclopropylacetamides as glucokinase activators
  申请人：Weichert Gerhard Andreas

  公开号：US20060111353A1

  公开（公告）日：2006-05-25

  According to the present invention there is provided a compounds of formula (I): and pharmaceutically acceptable salts thereof.

  根据本发明，提供了式（I）的化合物及其药学上可接受的盐。
• WO2006/75955
  申请人：——

  公开号：——

  公开（公告）日：——
• 5-Substituted-(1,2,3-triazol-4-yl)thiophene-2-sulfonamides strongly inhibit human carbonic anhydrases I, II, IX and XII: Solution and X-ray crystallographic studies
  作者：Janis Leitans、Agnese Sprudza、Muhammet Tanc、Igor Vozny、Raivis Zalubovskis、Kaspars Tars、Claudiu T. Supuran

  DOI：10.1016/j.bmc.2013.06.041

  日期：2013.9

  We report here a series of 2-thiophene-sulfonamides incorporating 1-substituted aryl-1,2,3-triazolyl moieties, prepared by click chemistry from 5-ethynylthiophene-2-sulfonamide and substituted aryl azides. The new sulfonamides were investigated as inhibitors of the zinc metalloenzyme CA (EC 4.2.1.1), and more specifically against the human (h) cytosolic isoforms hCA I and II and the transmembrane, tumor-associated ones hCA IX and XII: The new compounds were medium-weak hCA I inhibitors (K(I)s in the range of 224-7544 nM), but were compactly, highly effective, low nanomolar hCA II inhibitors (K(I)s of 2.2-7.7 nM). The tumor-associated hCA IX was inhibited with K(I)s ranging between 5.4 and 811 nM, whereas hCA XII with inhibition constants in the range of 3.4-239 nM. The X-ray crystal structure of the adducts of two such compounds bound to hCA II (one incorporating 1-naphthyl, the other one 3-cyanophenyl moieties) evidenced the reasons of the high affinity for hCA II. Highly favorable, predominantly hydrophobic interactions between the sulfonamide scaffold and the hCA II active site were responsible for the binding, in addition to the coordination of the sulfamoyl moiety to the zinc ion. The tails of the two inhibitors adopted very diverse orientations when bound to the active site, with the naphthyltriazolyl moiety orientated towards the hydrophobic half of the active site, and the 3-cyanophenyl one pointing towards the hydrophilic half. These data may be used for the structure-based drug design of even more effective hCA II inhibitors, with potential use as antiglaucoma agents or as diuretics. (C) 2013 Elsevier Ltd. All rights reserved.