4-氨基-N-(3-氯-1H-吲哚-7-基)苯磺酰胺 | 165668-25-7

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 中文名称: 4-氨基-N-(3-氯-1H-吲哚-7-基)苯磺酰胺
• 英文名称: 4-Amino-N-(3-chloro-1H-indole-7-yl)benzenesulfonamide
• 英文别名: indisulam；4-amino-N-(3-chloro-1H-indol-7-yl)benzenesulfonamide；Benzenesulfonamide, 4-amino-N-(3-chloro-1H-indol-7-yl)-
• CAS: 165668-25-7
• 化学式: C₁₄H₁₂ClN₃O₂S
• 分子量: 321.787
• InChiKey: BBZBFSPWJFJXHM-UHFFFAOYSA-N

物化性质

• 熔点：
  174.5-176 °C(Solv: ethanol (64-17-5); hexane (110-54-3))
• 沸点：
  591.5±60.0 °C(Predicted)
• 密度：
  1.567±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  21
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  96.4
• 氢给体数：
  3
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  甲基磺酰氯 、 4-氨基-N-(3-氯-1H-吲哚-7-基)苯磺酰胺 在 吡啶 作用下， 以90%的产率得到N-(3-Chloro-1H-indol-7-yl)-4-(methanesulfonamido)-benzenesulfonamide
  参考文献：
  名称：

  Discovery of Novel Antitumor Sulfonamides Targeting G1 Phase of the Cell Cycle

  摘要：

  Described herein is the discovery of a novel series of antitumor sulfonamides targeting G1 phase of the cell cycle. Cell cycle control in G1 phase has attracted considerable attention in recent cancer research, because many of the important proteins involved in G1 progression or G1/S transition have been found to play a crucial role in proliferation, differentiation, transformation, and programmed cell death (apoptosis). We previously reported our first antitumor sulfonamide E7010 as a novel tubulin polymerization inhibitor. Interestingly enough, continuous research on structurally related compounds led us to the finding of another class of antitumor sulfonamides that block cell cycle progression of P388 murine leukemia cells in GI phase, but not in M phase. Of the compounds examined, N-(3-chloro-7-indolyl)-1,4-benzenedisulfonamide (E7070) showed significant antitumor activity against HCT116 human colon carcinoma both in vitro (IC50 0.11 mu g/mL in cell proliferation assay) and in vivo (not only growth suppression but also a marked reduction of tumor size in nude mice). Because of its promising efficacy against human tumor xenografts and its unique mode of action, E7070 is currently undergoing phase I clinical trials in European countries.

  DOI：

  10.1021/jm9902638
• 作为产物：
  描述：

  7-氨基吲哚 在 吡啶 、 盐酸 、 N-氯代丁二酰亚胺 、 锌 作用下， 以 四氢呋喃 、 甲醇 为溶剂， 生成 4-氨基-N-(3-氯-1H-吲哚-7-基)苯磺酰胺
  参考文献：
  名称：

  新型N-（7-吲哚基）苯磺酰胺的聚焦化合物库，用于发现有效的细胞周期抑制剂。

  摘要：

  合成了一系列含有N-（7-吲哚基）苯磺酰胺药效基团的化合物，并将其作为潜在的抗肿瘤药进行了评估。用P388鼠白血病细胞进行的细胞周期分析表明，有两种不同类型的有效细胞周期抑制剂。一个破坏有丝分裂，另一个导致G1积累。本文描述了该药效团模板上取代基图案的SAR总结。

  DOI：

  10.1016/s0960-894x(00)00219-5

文献信息

• Integrin expression inhibitors
  申请人：——

  公开号：US20040018192A1

  公开（公告）日：2004-01-29

  The present invention provides an integrin expression inhibitor, and an agent for treating arterial sclerosis, psoriasis, cancer, retinal angiogenesis, diabetic retinopathy or inflammatory diseases, an anticoagulant, or a cancer metastasis suppressor on the basis of an integrin inhibitory action. Namely, it provides an integrin expression inhibitor comprising, as an active ingredient, a sulfonamide compound represented by the following formula (I), a pharmacologically acceptable salt thereof or a hydrate of them. 1 In the formula, B means a C6-C10 aryl ring or 6- to 10-membered heteroaryl ring which may have a substituent and in which a part of the ring may be saturated; K means a single bond, —CH═CH— or —(CR 4b R 5b ) m b — (wherein R 4b and R 5b are the same as or different from each other and each means hydrogen atom or a C1-C4 alkyl group; and m b means an integer of 1 or 2); R 1 means hydrogen atom or a C1-C6 alkyl group; Z means a single bond or —CO—NH—; and R means a C6-C10 aryl ring or 6- to 10-membered heteroaryl ring which may have a substituent and in which a part of the ring may be saturated, respectively.

  本发明提供了一种整合素表达抑制剂，以及基于整合素抑制作用的用于治疗动脉硬化、银屑病、癌症、视网膜血管生成、糖尿病视网膜病变或炎症性疾病的药剂、抗凝剂或癌症转移抑制剂。即提供了一种包含以下式(I)所表示的磺胺化合物、其药理学上可接受的盐或其水合物作为活性成分的整合素表达抑制剂。 在该式中，B表示一个C6-C10芳基环或6-至10成员杂芳基环，可能具有取代基，并且环的一部分可能是饱和的；K表示一个单键，-CH═CH-或-(CR 4b R 5b ) m b -（其中R 4b 和R 5b 相同或不同，各自表示氢原子或C1-C4烷基；m b 表示1或2的整数）；R 1 表示氢原子或C1-C6烷基；Z表示一个单键或-CO-NH-；R表示一个C6-C10芳基环或6-至10成员杂芳基环，可能具有取代基，并且环的一部分可能是饱和的，分别。
• Integrin expression inhibitor
  申请人：Wakabayashi Toshiaki

  公开号：US20050176712A1

  公开（公告）日：2005-08-11

  The present invention provides an integrin expression inhibitor, and an agent for treating arterial sclerosis, psoriasis, cancer, retinal angiogenesis, diabetic retinopathy or inflammatory diseases, an anticoagulant, or a cancer metastasis suppressor on the basis of an integrin inhibitory action. Namely, it provides an integrin expression inhibitor comprising, as an active ingredient, a sulfonamide compound represented by the following formula (I), a pharmacologically acceptable salt thereof or a hydrate of them, wherein in the formula, B means a C6-C10 aryl ring or 6- to 10-membered heteroaryl ring which may have a substituent and in which a part of the ring may be saturated; K means a single bond, —CH═CH— or —(CR 4b R 5b ) m b — (wherein R 4b and R 5b are the same as or different from each other and each means hydrogen atom or a C1-C4 alkyl group; and m b means an integer of 1 or 2); R 1 means hydrogen atom or a C1-C6 alkyl group; Z means a single bond or —CO—NH—; and R means a C6-C10 aryl ring or 6- to 10-membered heteroaryl ring which may have a substituent and in which a part of the ring may be saturated, respectively.

  本发明提供了一种整合素表达抑制剂，并提供了一种基于整合素抑制作用的用于治疗动脉硬化、银屑病、癌症、视网膜血管生成、糖尿病视网膜病变或炎症性疾病的药剂、抗凝剂或癌症转移抑制剂。换句话说，本发明提供了一种整合素表达抑制剂，其包括以下式（I）所表示的磺酰胺化合物作为活性成分、其药学上可接受的盐或其水合物： 其中，在上述式中，B表示C6-C10芳基环或6-至10元杂环芳基环，其中可能有取代基，并且环的一部分可能是饱和的；K表示单键，-CH═CH-或-(CR4bR5b)mb-（其中R4b和R5b相同或不同，每个表示氢原子或C1-C4烷基；mb表示1或2的整数）；R1表示氢原子或C1-C6烷基；Z表示单键或-CO-NH-；R分别表示C6-C10芳基环或6-至10元杂环芳基环，其中可能有取代基，并且环的一部分可能是饱和的。
• INTEGRIN EXPRESSION INHIBITOR
  申请人：WAKABAYASHI Toshiaki

  公开号：US20100267754A1

  公开（公告）日：2010-10-21

  The present invention provides an integrin expression inhibitor, and an agent for treating arterial sclerosis, psoriasis, cancer, retinal angiogenesis, diabetic retinopathy or inflammatory diseases, an anticoagulant, or a cancer metastasis suppressor on the basis of an integrin inhibitory action. Namely, it provides an integrin expression inhibitor comprising, as an active ingredient, a sulfonamide compound represented by the following formula (I), a pharmacologically acceptable salt thereof or a hydrate of them, wherein in the formula, B means a C6-C10 aryl ring or 6- to 10-membered heteroaryl ring which may have a substituent and in which a part of the ring may be saturated; K means a single bond, —CH═CH— or —(CR 4b R 5b ) m b — (wherein R 4b and R 5b are the same as or different from each other and each means hydrogen atom or a C1-C4 alkyl group; and m b means an integer of 1 or 2); R 1 means hydrogen atom or a C1-C6 alkyl group; Z means a single bond or —CO—NH—; and R means a C6-C10 aryl ring or 6- to 10-membered heteroaryl ring which may have a substituent and in which a part of the ring may be saturated, respectively.

  本发明提供了一种整合素表达抑制剂，以及一种用于治疗动脉硬化、银屑病、癌症、视网膜血管生成、糖尿病视网膜病变或炎症性疾病、抗凝剂或癌症转移抑制剂的药剂，其基于整合素抑制作用。即，提供一种整合素表达抑制剂，其包括以下式（I）所表示的磺酰胺化合物作为活性成分，其药理学上可接受的盐或水合物，其中在该式中，B表示一个C6-C10芳基环或6-到10成员杂环环，可以有取代基，在环中的一部分可能是饱和的；K表示单键，—CH═CH—或—（CR4bR5b）mb—（其中R4b和R5b相同或不同，每个表示氢原子或C1-C4烷基；mb表示1或2的整数）；R1表示氢原子或C1-C6烷基；Z表示单键或—CO—NH—；R分别表示C6-C10芳基环或6-到10成员杂环环，可以有取代基，在环中的一部分可能是饱和的。
• BICYCLIC HETEROCYCLIC SULFONAMIDE AND SULFONIC ESTER DERIVATIVES
  申请人：Eisai Co., Ltd.

  公开号：EP0673937A1

  公开（公告）日：1995-09-27

  Novel bicyclic heterocyclic sulfonamide and sulfonic ester derivatives represented by general formula (I) having an antitumor activity and a reduced toxicity, pharmacologically acceptable salts thereof, and a process for producing the same; wherein ring A represents an optionally substituted mono- or bicyclic aromatic group; ring B represents an optionally substituted 6-membered unsaturated hydrocarbon ring or 6-membered unsaturated heterocyclic group containing one nitrogen atom; ring C represents an optionally substituted 5-membered heterocyclic group containing one or two nitrogen atoms; W represents a single bond or -CH=CH-; X represents -NR¹- or oxygen; Y represents carbon or nitrogen; Z represents -NR²- or nitrogen; and R¹ and R² represent each independently hydrogen or lower alkyl.

  由通式(I)代表的具有抗肿瘤活性且毒性降低的新型双环杂环磺酰胺和磺酸酯衍生物、其药理学上可接受的盐，以及生产该衍生物的工艺；其中环A代表任选取代的单环或双环芳香基团，环B代表任选取代的6元不饱和烃环或含有一个氮原子的6元不饱和杂环基团；环C代表任选取代的5元杂环基团；环 B 代表任选取代的含一个氮原子的 6 元不饱和烃环或 6 元不饱和杂环基团； 环 C 代表任选取代的含一个或两个氮原子的 5 元杂环基团； W 代表单键或-CH=CH-； X 代表-NR¹-或氧； Y 代表碳或氮； Z 代表-NR²-或氮；以及 R¹ 和 R² 各自独立地代表氢或低级烷基。
• INTEGRIN EXPRESSION INHIBITORS
  申请人：Eisai Co., Ltd.

  公开号：EP1258252A1

  公开（公告）日：2002-11-20

  The present invention provides an integrin expression inhibitor, and an agent for treating arterial sclerosis, psoriasis, cancer, retinal angiogenesis, diabetic retinopathy or inflammatory diseases, an anticoagulant, or a cancer metastasis suppressor on the basis of an integrin inhibitory action. Namely, it provides an integrin expression inhibitor comprising, as an active ingredient, a sulfonamide compound represented by the following formula (I), a pharmacologically acceptable salt thereof or a hydrate of them. In the formula, B means a C6-C10 aryl ring or 6- to 10-membered heteroaryl ring which may have a substituent and in which a part of the ring may be saturated; K means a single bond, -CH=CH- or - (CR4bR5b)mb- (wherein R4b and R5b are the same as or different from each other and each means hydrogen atom or a C1-C4 alkyl group; and mb means an integer of 1 or 2); R1 means hydrogen atom or a C1-C6 alkyl group; Z means a single bond or -CO-NH-; and R means a C6-C10 aryl ring or 6- to 10-membered heteroaryl ring which may have a substituent and in which a part of the ring may be saturated, respectively.

  本发明提供了一种整合素表达抑制剂，以及一种基于整合素抑制作用的用于治疗动脉硬化、银屑病、癌症、视网膜血管生成、糖尿病视网膜病变或炎症性疾病的制剂、抗凝剂或癌症转移抑制剂。也就是说，它提供了一种整合素表达抑制剂，其活性成分包括下式(I)代表的磺酰胺化合物、其药理学上可接受的盐或它们的水合物。 式中，B 指 C6-C10 芳基环或 6 至 10 元杂芳基环，可具有取代基，其中环的一部分可为饱和；K 指单键、-CH=CH- 或-(CR4bR5b)mb-（其中 R4b 和 R5b 彼此相同或不同，各自指氢原子或 C1-C4 烷基；R1指氢原子或C1-C6烷基；Z指单键或-CO-NH-；R指C6-C10芳基环或6-至10元杂芳基环，可分别具有一个取代基，其中环的一部分可为饱和。