N-isobutyrylbenzenesulfonamide | 7242-84-4

• 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-isobutyrylbenzenesulfonamide
• 英文别名: N-Phenylsulfonyl-isobutyramid；N-(phenylsulfonyl)isobutyramide；N-isobutanoyl-benzenesulfonamide；2,2-Dimethyl-N-(phenylsulfonyl)acetamide；N-(benzenesulfonyl)-2-methylpropanamide
• CAS: 7242-84-4
• 化学式: C₁₀H₁₃NO₃S
• mdl: MFCD25966641
• 分子量: 227.284
• InChiKey: YWYSZMYFYSMUOM-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.9
• 重原子数：
  15
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.3
• 拓扑面积：
  71.6
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  N-isobutyrylbenzenesulfonamide 在 lithium diisopropyl amide 作用下， 以 四氢呋喃 为溶剂， 以58%的产率得到3-丙-2-基-1,2-苯并噻唑1,1-二氧化物
  参考文献：
  名称：

  Aromatic heteroannulation via metalation-cyclization of N-acyl-2-chlorobenzenesulfonamides and N-acylbenzenesulfonamides

  摘要：

  N-Acyl-2-chlorobenzenesulfonamides 7a-d undergo competitive metal-halogen exchange and or alpha-deprotonation reactions when treated sequentially with sodium hydride and n-butyllithium. The o-lithio intermediates derived from metal-halogen exchange and ortho-deprotonation undergo cyclization to afford 3-substituted 1,2-benzisothiazole 1,1-dioxides 10a-d and 3-substituted 7-chloro-1,2-benzisothiazole 1,1-dioxides 14a-d, respectively. Reaction time-temperature data show evidence for the slow conversion of the lateral dianion of N-acetyl-2-chlorobenzenesulfonamide (7a) to the corresponding N,ortho-dialkali salt. 1,2-Benzisothiazole 1,1-dioxides 14a-d were obtained in good yield and free from products resulting from metal-halogen exchange by treatment of sulfonamides 7a-d with 2 equiv of LDA in THF. In the presence of 2 equiv of LDA, N-acylbenzenesulfonamides devoid of or containing only weakly acidic alpha-hydrogens undergo alpha-deprotonation-cyclization to afford the respective 1,2-benzoisothiazole 1,1-dioxides.

  DOI：

  10.1021/jo00046a012
• 作为产物：
  描述：

  苯磺酰胺 、 异丁酸酐 在 HClO₄-SiO₂ 作用下， 反应 0.08h， 以96%的产率得到N-isobutyrylbenzenesulfonamide
  参考文献：
  名称：

  HClO4-SiO2 and NaHSO4-SiO2: Two Efficient Heterogeneous Catalysts for Synthesis of N-Acylsulfonamides under Solvent-free Conditions

  摘要：

  已经通过在无溶剂条件下，使用HClO4-SiO2或NaHSO4-SiO2的存在下，将磺酰胺与酸酐反应，成功实现了一种简单高效的N-酰基磺酰胺合成。

  DOI：

  10.2174/157017809787893019

文献信息

• INHIBITORS OF UDP-GALACTOPYRANOSE MUTASE
  申请人：WISCONSIN ALUMNI RESEARCH FOUNDATION

  公开号：US20170258805A1

  公开（公告）日：2017-09-14

  Compounds and salts thereof which are acyl-sulfonamides or certain carboxylic acids and which inhibit microbial growth or attenuate the virulence of pathogenic microorganisms and which inhibit UDP-galactopyranose mutase (UGM). Compounds of the invention include 2-aminothiazoles and triazolothiadiazines, particularly 3,6,7-substituted-7H-[1,2,4]triazolo[3,4-b][1,3,4]thiadiazines, and 2-amino and salts thereof. Methods for inhibiting growth or attenuating virulence of microbial pathogens including mycobacterium , for example, M. tuberculosis and M. smegmatis and Klebsiella , for example, Klebsiella pneumoniae . Methods for inhibiting eukaryotic human and animal pathogens, and fungi and nematodes in particular. Methods for treatment of infections by prokaryotic and eukaryotic pathogens employing compounds of the invention.

  其酰基磺酰胺或某些羧酸的化合物及其盐，能够抑制微生物生长或减弱病原微生物的毒力，并且能够抑制UDP-半乳糖吡喃糖异构酶（UGM）。该发明的化合物包括2-氨基噻唑和三唑噻二嗪，特别是3,6,7-取代的7H-[1,2,4]三唑噻二嗪和其盐，以及2-氨基。抑制微生物病原体生长或减弱其毒力的方法包括结核分枝杆菌（例如结核分枝杆菌和平滑分枝杆菌）和克雷伯氏菌（例如肺炎克雷伯氏菌）等微生物病原体。抑制真核人类和动物病原体、真菌和线虫的方法，特别是治疗原核和真核病原体感染的方法，采用了该发明的化合物。
• Facile Synthesis of<i>N</i>‐Acylsulfonamide in the Presence of Silica Chloride (SiO₂‐Cl) both under Heterogeneous and Solvent‐Free Conditions
  作者：Ahmad Reza Massah、Ahmad Reza Momeni、Mina Dabagh、Hamid Aliyan、Hamid Javaherian Naghash

  DOI：10.1080/00397910701750185

  日期：2008.1

  Abstract Sulfonamides were converted to the corresponding N‐acyl sulfonamides with carboxylic acid chlorides and anhydrides in the presence of silica chloride. All reactions were performed in both heterogeneous and solvent‐free conditions. This method provides the N‐acyl sulfonamides products in good to high yield and purity.

  摘要 在氯化硅存在下，磺酰胺与羧酸氯化物和酸酐一起转化为相应的 N-酰基磺酰胺。所有反应均在非均相和无溶剂条件下进行。该方法提供了良好至高产率和纯度的 N-酰基磺酰胺产品。
• Synthesis, in vitro antibacterial and carbonic anhydrase II inhibitory activities of N-acylsulfonamides using silica sulfuric acid as an efficient catalyst under both solvent-free and heterogeneous conditions
  作者：Ahmad Reza Massah、Hadi Adibi、Reza Khodarahmi、Ramin Abiri、Mohammad Bagher Majnooni、Sherita Shahidi、Beheshteh Asadi、Masomeh Mehrabi、Mohammad Ali Zolfigol

  DOI：10.1016/j.bmc.2008.04.011

  日期：2008.5

  Silica sulfuric acid catalyzes efficiently the reaction of sulfonamides with both carboxylic acid anhydrides and chlorides under solvent-free and heterogeneous conditions. All the reactions were done at room temperature and the N-acylsulfonamides were obtained with high yields and purity via an easy work-up procedure. This method is attractive and is in a close agreement with green chemistry. These

  二氧化硅硫酸可在无溶剂和非均相条件下有效催化磺酰胺与羧酸酐和氯化物的反应。所有反应均在室温下进行，并且通过简单的后处理程序以高收率和纯度获得了N-酰基磺酰胺。该方法是有吸引力的，并且与绿色化学密切相关。还研究了这些化合物的抗菌活性，包括革兰氏阳性球菌和革兰氏阴性杆菌，以及碳酸酐酶II的抑制活性。
• THERAPEUTIC CYCLOPENTANE DERIVATIVES
  申请人：Donde Yariv

  公开号：US20070270387A1

  公开（公告）日：2007-11-22

  Disclosed herein is a compound having a structure or a pharmaceutically acceptable salt, or a prodrug thereof. Therapeutic methods, compositions, and medicaments related thereto are also disclosed.

  本文披露了一种具有结构或药用可接受盐或其前药的化合物。还披露了与之相关的治疗方法、组合物和药物。
• THERAPEUTIC SUBSTITUTED HYDANTOINS AND RELATED COMPOUNDS
  申请人：Old David W.

  公开号：US20080058397A1

  公开（公告）日：2008-03-06

  A compound having a structure is disclosed herein. Therapeutic methods, compositions, and medicaments related thereto are also disclosed.

  本文披露了一种具有结构的化合物。同时还披露了与其相关的治疗方法、组合物和药物。