4-formyl-N-phenylbenzenesulfonamide | 179057-22-8

• 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: 4-formyl-N-phenylbenzenesulfonamide
• CAS: 179057-22-8
• 化学式: C₁₃H₁₁NO₃S
• 分子量: 261.301
• InChiKey: UXDLSZMIQCYMSC-UHFFFAOYSA-N

物化性质

• 熔点：
  98-99 °C
• 沸点：
  442.8±47.0 °C(Predicted)
• 密度：
  1.373±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.7
• 重原子数：
  18
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  71.6
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  4-formyl-N-phenylbenzenesulfonamide 在 sodium tetrahydroborate 作用下， 以 乙醇 为溶剂， 生成 4-[(cycloheptylamino)methyl]-N-phenylbenzenesulfonamide
  参考文献：
  名称：

  Inhibitors of acyl-CoA: cholesterol O-acyltransferase (ACAT). Part 1: Identification and structure-activity relationships of a novel series of substituted N-alkyl-N-biphenylylmethyl-N′-arylureas

  摘要：

  A series of N-alkyl-N-biphenylylmethyl-N'-arylurea and related derivatives represented by 1 have been prepared and evaluated for their ability to inhibit acyl-CoA:cholesterol O-acyltransferase in vitro and to lower plasma cholesterol levels in cholesterol-fed rats in vivo. Linking of two phenyl groups via oxygen and introduction of fluorine at appropriate positions on the biphenyl moiety improved in vitro and in vivo activity, From this series of analogs, compound 40 (FR179254), which had potent in vitro potency (rabbit intestinal microsomes IC50 = 25 nM), showed excellent plasma cholesterol-lowering activity when administered via the diet (ED50 = 0.045 mg/kg). However, the hypocholesterolemic effect of this compound was moderate when dosed by oral gavage in PEG400 as a vehicle (ED50 = 5.3 mg/kg). Modification of the N'-aryl moiety led to the identification of compound 50 (FR182980) which was efficacious in both dosing models (ED50 = 0.034 mg/kg and 0.11 mg/kg, respectively). (C) 1998 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0968-0896(97)10009-8
• 作为产物：
  描述：

  乙酰氧基-(4-氯磺酰基苯基)乙酸甲酯 在 吡啶 、 盐酸 作用下， 生成 4-formyl-N-phenylbenzenesulfonamide
  参考文献：
  名称：

  Sekikawa; Kakimoto, Nippon Kagaku Zasshi, 1952, vol. 73, p. 587

  摘要：

  DOI：

文献信息

• Discovery of trans-3-(pyridin-3-yl)acrylamide-derived sulfamides as potent nicotinamide phosphoribosyltransferase (NAMPT) inhibitors for the potential treatment of cancer
  作者：Kuojun Zhang、Yong Ni、Jiaxuan Chen、Zhengchao Tu、Xiaoxing Wu、Dong Chen、Hequan Yao、Sheng Jiang

  DOI：10.1016/j.bmcl.2019.04.013

  日期：2019.6

  Nicotinamide phosphoribosyltransferase (NAMPT) has emerged as a promising target for the discovery of anticancer drugs. Based on NAMPT inhibitor FK866 that has been advanced into phase II trial, we identified a trans-3-(pyridin-3-yl)acrylamide compound 13 incorporating with a biarylsulfanilamide moiety as a new NAMPT inhibitor. Further structure-activity relationship (SAR) exploration led to additional

  烟酰胺磷酸核糖基转移酶（NAMPT）已成为发现抗癌药物的有希望的靶标。基于已进入II期试验的NAMPT抑制剂FK866，我们确定了与联芳基磺酰胺基结合的反式3-（吡啶-3-基）丙烯酰胺化合物13作为新的NAMPT抑制剂。进一步的结构活性关系（SAR）的探索导致了更多的具有高体外NAMPT抑制能力和抗增殖活性的联芳基磺酰胺衍生物。特别是，最有效的NAMPT抑制剂化合物23（IC50 = 5.08 nM）对DU145，Hela和H1975细胞表现出一位数的纳摩尔抗增殖活性，IC50值分别为2.90 nM，2.34 nM和2.24 nM。甚至针对K562，MCF-7和HUH7细胞的亚纳摩尔水平，IC50值为0.46 nM，0。分别为23 nM和0.53 nM。我们的发现为发现更有效的NAMPT抑制剂作为抗癌药物提供了有希望的先导化合物。
• Carbamic acid compounds comprising a sulfonamide linkage as HDAC inhibitors
  申请人：Kalvinsh Ivars

  公开号：US20070004806A1

  公开（公告）日：2007-01-04

  This invention pertains to certain active carbamic acid compounds which inhibit HDAC activity and which have the following formula: (I) A is an aryl group; Q 1 is a covalent bond or an aryl leader group; J is a sulfonamide linkage selected from: —S(═O) 2 NR 1 — and —NR 1 S(═O) 2 —; R 1 is a sulfonamido substituent; and, Q 2 is an acid leader group; with the proviso that if J is —S(═O) 2 NR 1 —, then Q 1 is an aryl leader group; and pharmaceutically acceptable salts, solvates, amides, esters, ethers, chemically protected forms, and prodrugs thereof. The present invention also pertains to pharmaceutical compositions comprising such compounds, and the use of such compounds and compositions, both in vitro and in vivo, to inhibit HDAC, and, e.g., to inhibit proliferative conditions, such as cancer and psoriasis.

  本发明涉及抑制HDAC活性的某些活性碳酸酰化合物，其具有以下式子：（I）其中A是芳基；Q1是共价键或芳基引导基团；J是选自磺酰胺连接的以下链：—S（═O）2NR1—和—NR1S（═O）2—；R1是磺酰胺取代基；Q2是酸引导基团；但是，如果J是—S（═O）2NR1—，则Q1是芳基引导基团；以及其药学上可接受的盐，溶剂化物，酰胺，酯，醚，化学保护形式和前药。本发明还涉及包含这种化合物的制药组合物，以及在体内外使用这种化合物和组合物抑制HDAC，例如抑制增殖性疾病，如癌症和银屑病。
• CARBAMIC ACID COMPOUNDS COMPRISING A SULFONAMIDE LINKAGE AS HDAC INHIBITORS
  申请人：Watkins Clare J.

  公开号：US20080161401A1

  公开（公告）日：2008-07-03

  This invention pertains to certain active carbamic acid compounds which inhibit HDAC activity and which have the following formula: (I) A is an aryl group; Q 1 is a covalent bond or an aryl leader group; J is a sulfonamide linkage selected from: —S(═O) 2 NR 1 — and —NR 1 S(═O) 2 —; R 1 is a sulfonamido substituent; and, Q 2 is an acid leader group; with the proviso that if J is —S(═O) 2 NR 1 —, then Q 1 is an aryl leader group; and pharmaceutically acceptable salts, solvates, amides, esters, ethers, chemically protected forms, and prodrugs thereof. The present invention also pertains to pharmaceutical compositions comprising such compounds, and the use of such compounds and compositions, both in vitro and in vivo, to inhibit HDAC, and, e.g., to inhibit proliferative conditions, such as cancer and psoriasis.

  本发明涉及某些活性碳酰胺酸化合物，其抑制HDAC活性，具有以下公式：（I）其中，A是芳基基团；Q1是共价键或芳基引导基团；J是从以下选择的磺酰胺键连接：—S（═O）2NR1—和—NR1S（═O）2—；R1是磺酰胺取代基；Q2是酸引导基团；但是，如果J是—S（═O）2NR1—，则Q1是芳基引导基团；以及其药学上可接受的盐，溶剂化合物，酰胺，酯，醚，化学保护形式和前药。本发明还涉及包含这种化合物的制药组合物，以及在体内外使用这种化合物和组合物来抑制HDAC，例如，抑制增殖性疾病，如癌症和牛皮癣。
• Design and evaluation of novel analogs of 2-amino-4-boronobutanoic acid (ABBA) as inhibitors of human gamma-glutamyl transpeptidase
  作者：Luong Nguyen、Daniel C. Schultz、Simon S. Terzyan、Mohammad Rezaei、Jinhua Songb、Chenglong Li、Youngjae You、Marie H. Hanigan

  DOI：10.1016/j.bmc.2022.116986

  日期：2022.11

  site. The structure was interrogated to identify interactions between the enzyme and the inhibitor. Based on these data, a series of novel ABBA analogs were designed and synthesized. Their inhibitory activity against the hydrolysis and transpeptidation activities of hGGT1 were determined. The lead compounds were crystalized with hGGT1 and the structures solved. The kinetic data and structures of the complexes

  治疗癌症、心血管疾病和其他疾病需要γ-谷氨酰转肽酶（GGT1，又名γ-谷氨酰转移酶）抑制剂。抑制 GGT1 的化合物已在临床中进行了评估，但尚无抑制剂成功证明具有特异性和全身性的 GGT1 抑制作用。所有这些都有严重的副作用。L-2-氨基-4-硼丁酸 ( l -ABBA) 是一种谷氨酸类似物，是体外最有效的 GGT1 抑制剂。在这项研究中，我们解析了活性位点结合有 ABBA 的人 GGT1 (hGGT1) 的晶体结构。研究该结构以确定酶和抑制剂之间的相互作用。基于这些数据，设计并合成了一系列新型 ABBA 类似物。测定了它们对 hGGT1 水解和转肽活性的抑制活性。先导化合物用 hGGT1 结晶并解析结构。复合物的动力学数据和结构为蛋白质结构动力学在开发抑制 hGGT1 的化合物中的关键作用提供了新的见解。
• Compositions for repelling crawling insects
  申请人：——

  公开号：US20020094993A1

  公开（公告）日：2002-07-18

  The present invention relates to novel compositions, comprising a repellent and an additive, where the additive is selected from the group consisting of phenol, benzaldehyde, benzoic acid or derivatives thereof and is present in a ratio of from 10:100 to 200:100% by weight to the repellent, and to their use for repelling crawling harmful insects, in particular ants or cockroaches.

  本发明涉及新型组合物，包括一种驱虫剂和一种添加剂，其中所述添加剂选自苯酚、苯甲醛、苯甲酸或其衍生物组成的群体，并以10:100至200:100％重量的比例存在于驱虫剂中，以及其用于驱赶爬行有害昆虫，特别是蚂蚁或蟑螂。