N-[(4-chlorophenyl)carbamoyl]sulfamoyl chloride | 181428-37-5

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: N-[(4-chlorophenyl)carbamoyl]sulfamoyl chloride
• CAS: 181428-37-5
• 化学式: C₇H₆Cl₂N₂O₃S
• 分子量: 269.108
• InChiKey: ISWCJIRGLVIKIV-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.95
• 重原子数：
  15.0
• 可旋转键数：
  2.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  75.27
• 氢给体数：
  2.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  N-[(4-chlorophenyl)carbamoyl]sulfamoyl chloride 在 aluminum (III) chloride 、 硫酸 、 sodium ethanolate 、 三乙胺 作用下， 以 乙醇 、 二氯甲烷 、 水 为溶剂， 反应 2.0h， 生成 7-chloro-N-(2,2-dimethyl-6-nitro-3,4-dihydro-2H-1-benzopyran-4-yl)-4H-1,2,4-benzothiadiazine-3-carboxamide 1,1-dioxide
  参考文献：
  名称：

  Synthesis and pharmacological activity of N-(2,2-dimethyl-3,4-dihydro-2H-1-benzopyran-4-yl)-4H-1,2,4-benzothiadiazine-3-carboxamides 1,1-dioxides on rat uterus, rat aorta and rat pancreatic β-cells

  摘要：

  N-(2,2-Dimethyl-3,4-dihydro-2H-1-benzopyran-4-yl)-4H-1,2,4-benzothiadiazine-3-carboxamides 1,1-dioxides were prepared and evaluated on rat uterus, rat aortic rings and rat pancreatic beta-cells. Pharmacological studies conducted on rat uterus indicated that several of these original hybrid compounds displayed a strong myorelaxant activity. The most active compounds hold a bromine atom at the 6-position of the dihydrobenzopyran ring. Moreover, the compounds failed to display a marked inhibitory effect on insulin secretion and vascular myogenic activity. These features suggest that the 6-bromo compounds could be relatively selective towards the uterine smooth muscle. (C) 2012 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2012.05.011
• 作为产物：
  描述：

  氯磺酰异氰酸酯 、 对氯苯胺 以 1,4-二氧六环 、 乙醚 为溶剂， 反应 1.0h， 生成 N-[(4-chlorophenyl)carbamoyl]sulfamoyl chloride
  参考文献：
  名称：

  杂环磺酰脲的合成†

  摘要：

  我们检查了以前报道的一键合成色酮-3-磺酰脲的范围[1]。由此使不同的苯胺和杂环胺与氯磺酰基异氰酸酯衍生的氯磺酰脲反应。将它们用不同的烯胺酮和烯胺处理以提供标题化合物。

  DOI：

  10.1002/jhet.5570330340

文献信息

• Synthesis of flavone-3-sulfonylureas
  作者：Werner Löwe、Norbert Matzanke

  DOI：10.1002/jhet.5570330364

  日期：1996.5

  The synthesis of new flavone-3-sulfonylurea derivatives is hereby described. The influence of a phenyl group in the 2-position and an acetate group in the 8-position at the chromone nucleus on the activity was studied. Only weak cytostatic activity of the new compounds was found.

  因此描述了新的黄酮-3-磺酰脲衍生物的合成。研究了色酮核中2-位的苯基和8位的乙酸酯基对活性的影响。仅发现新化合物的弱细胞抑制活性。
• 一种苯并噻二嗪酮类衍生物，其制备方法和用 途
  申请人：深圳海王医药科技研究院有限公司

  公开号：CN107056731B

  公开（公告）日：2019-12-10

  本发明提供了具有如式(I)所示结构的化合物及其制备方法。本发明还提供了该类化合物在预防和治疗糖尿病并发症药物中的应用，以及含有这些化合物的药物组合物。本发明的化合物对ALR2抑制活性和ALR1抑制活性具有高选择性，在高糖环境下对细胞有保护作用，化合物在大鼠的体内药物半衰期较长，在血液中浓度较高，其对STZ诱导糖尿病大鼠的坐骨运动神经传导损伤、坐骨感觉神经传导损伤有明显修复作用且效果较好，明显加快了感觉神经纤维A‑fiber和C‑fiber的传导速度，显著降低了大鼠坐骨神经中山梨醇，表现出良好的动物安全性。
• An efficient one‐pot synthesis of <i>N</i> ‐(substituted phenyl)‐1,2,5‐thiadiazolidine‐2‐carboxamide 1,1‐dioxide derivatives
  作者：Sihem Hessainia、Abbes Boukhari、Zinelaabidine Cheraiet

  DOI：10.1002/jhet.3767

  日期：2020.1

  heterocyclic compounds synthesized by multicomponent condensation reaction in one pot of aniline, chlorosulfonyl isocyanate, and 2‐chloroethylamine hydrochloride which is used as a useful precursor under mild conditions. This reaction is realized with high atom economy, at room temperature and in a short reaction time. Series of these desired products are obtained from good to excellent yields within 2 hours

  1,2,5-噻二唑烷-1,1-二氧化物羧酰胺衍生物3a-3n是在一锅苯胺，氯磺酰基异氰酸酯和2-氯乙胺盐酸盐中经多组分缩合反应合成的新型杂环化合物，在温和的条件下可用作有用的前体情况。在室温下且反应时间短的情况下，以高原子经济性实现了该反应。在所有情况下，都可以在2小时内以良好的良率获得一系列所需的产品。所有合成的化合物均通过1 H，13 C NMR，MS和HMBC / HSQC光谱进行表征。
• 5′-Alkyl-benzothiadiazides: A New Subgroup of AMPA Receptor Modulators with Improved Affinity
  作者：Dean Phillips、Jennifer Sonnenberg、Amy C Arai、Rishi Vaswani、Peter O Krutzik、Thomas Kleisli、Markus Kessler、Richard Granger、Gary Lynch、A Richard Chamberlin

  DOI：10.1016/s0968-0896(01)00405-9

  日期：2002.5

  AMPA receptors form a major subdivision of the glutamate receptor family that mediates excitatory synaptic transmission in the brain, Currents through AMPA receptors can be up- or down-regulated by compounds that allosterically modulate receptor kinetics through binding sites distinct from that for glutamate. One of those modulators is the benzothiadiazide IDRA-21 which has been reported to enhance synaptic transmission and be effective in behavioral tests, but typically requires threshold concentrations of at least 100 muM to be active in vitro. In this study, new benzothiadiazides were developed with IDRA-21 as lead compound and examined for their potency in modulating AMPA receptor kinetics. A significant increase in drug affinity was obtained by alkyl substitution at the 5'-position of IDRA-21; substitutions at other positions of the benzothiadiazide core generally did not yield a further gain in affinity and in some cases abolished drug binding. The 5'-ethyl derivative exhibited an EC50 value in the order of 22 muM which represents about a 30-fold gain in affinity over that of IDRA-21. The EC50 value is comparable to that of cyclothiazide, the most potent benzothiadiazide drug, but the effects on AMPA receptors differed substantially between these two compounds in that the 5'-ethyl derivative of IDRA-21 greatly increased the binding affinity for receptor agonists whereas cyclothiazide is known to reduce agonist binding. The structure-activity relationships reported here thus offer to provide new insights how receptor kinetics is linked to particular aspects of receptor-drug interactions. (C) 2002 Published by Elsevier Science Ltd.
• Acetic Acid Derivatives of 3,4-Dihydro-2<i>H</i>-1,2,4-benzothiadiazine 1,1-Dioxide as a Novel Class of Potent Aldose Reductase Inhibitors
  作者：Xin Chen、Changjin Zhu、Fan Guo、Xiaowei Qiu、Yanchun Yang、Shuzhen Zhang、Minlan He、Shagufta Parveen、Chaojun Jing、Yan Li、Bing Ma

  DOI：10.1021/jm100962a

  日期：2010.12.9

  A series of novel benzothiadiazine 1,1-dioxide derivatives were synthesized and tested for their inhibitory activity against aldose reductase. Of these derivatives, 17 compounds, having a substituted N2-benzyl group and a N4-acetic acid group on the benzothiadiazine, were found to be potent and selective aldose reductase inhibitors in vitro with IC50 values ranging from 0.032 to 0.975 mu M. 9m proved to be the most active in vitro. The eight top-scoring compounds coming from the in vitro test for ALR2 inhibition activity were then tested in vivo, whereby three derivatives, 9i, 9j, and 9m, demonstrated a significantly preventive effect on sorbitol accumulation in the sciatic nerve in the 5-day streptozotocin-induced diabetic rats in vivo. Structure activity relationship and molecular docking studies highlighted the importance of substitution features of N4-acetic acid group and halogen-substituted N2-benzyl group in the benzothiadiazine scaffold and indicated that substitution with hallogen at C-7 had a remarkably strong effect on ALR2 inhibition potency.