2,4-dichloro-5-(carbazoyl)benzenesulfonamide | 18648-15-2

• 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: 2,4-dichloro-5-(carbazoyl)benzenesulfonamide
• 英文别名: 2,4-Dichloro-5-sulfamoylbenzhydrazide；2,4-dichloro-5-(hydrazinecarbonyl)benzenesulfonamide
• CAS: 18648-15-2
• 化学式: C₇H₇Cl₂N₃O₃S
• mdl: MFCD00453745
• 分子量: 284.123
• InChiKey: VONGMLDKMLCQMK-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.3
• 重原子数：
  16
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  124
• 氢给体数：
  3
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  2,4-dichloro-5-(carbazoyl)benzenesulfonamide 在 盐酸 、 sodium nitrite 作用下， 以 水 为溶剂， 以74%的产率得到2,4-dichloro-5-sulfamoylbenzoyl azide
  参考文献：
  名称：

  Carbonic anhydrase inhibitors. Synthesis of a novel series of 5-substituted 2,4-dichlorobenzenesulfonamides and their inhibition of human cytosolic isozymes I and II and the transmembrane tumor-associated isozymes IX and XII

  摘要：

  A series of novel 5-substituted 2,4-dichlorobenzenesulfonamides 5a-c, 6a-d, 7a-j and 10a-i have been synthesized and investigated as inhibitors of four isoforms of zinc enzyme carbonic anhydrase (CA.EC 4.2.1.1), that is the cytosolic CA I and II, and tumor-associated isozymes CA IX and XII. Against the human CA I investigated compounds displayed K-I values from 349 to 7355 nM, toward hCA II at range of 6.9 to 164 nM, while against hCA IX ranging from 2.8 to 76 nM and against hCA XII in the range of 2.7 to 95 nM. The excellent inhibitory activity against tumor-associated hCA IX was found. The twenty one new compounds displayed a powerful inhibitory potency toward hCA IX (K-I = 2.8-21.7 nM) in comparison with the clinically used CAIs AAZ, MZA, EZA, DCP and IND (24-50 nM). Among them the most potent hCA IX inhibitor 7b (K-I = 2.8 nM) was 8.5-fold stronger than IND (K-I = 24 nM). Toward tumor-associated hCA XII compounds 6c and 10a (K-I = 2.7 and 2.8 nM, respectively) showed a better inhibitory potency than reference sulfonamides MZA and IND (K-I = 3.4 nM). (C) 2014 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2014.05.039
• 作为产物：
  描述：

  2,4-二氯-5-磺酰胺基苯甲酸 在 氯化亚砜 、 hydrazine hydrate 作用下， 以 乙醇 为溶剂， 反应 9.0h， 生成 2,4-dichloro-5-(carbazoyl)benzenesulfonamide
  参考文献：
  名称：

  Carbonic anhydrase inhibitors. Synthesis of a novel series of 5-substituted 2,4-dichlorobenzenesulfonamides and their inhibition of human cytosolic isozymes I and II and the transmembrane tumor-associated isozymes IX and XII

  摘要：

  A series of novel 5-substituted 2,4-dichlorobenzenesulfonamides 5a-c, 6a-d, 7a-j and 10a-i have been synthesized and investigated as inhibitors of four isoforms of zinc enzyme carbonic anhydrase (CA.EC 4.2.1.1), that is the cytosolic CA I and II, and tumor-associated isozymes CA IX and XII. Against the human CA I investigated compounds displayed K-I values from 349 to 7355 nM, toward hCA II at range of 6.9 to 164 nM, while against hCA IX ranging from 2.8 to 76 nM and against hCA XII in the range of 2.7 to 95 nM. The excellent inhibitory activity against tumor-associated hCA IX was found. The twenty one new compounds displayed a powerful inhibitory potency toward hCA IX (K-I = 2.8-21.7 nM) in comparison with the clinically used CAIs AAZ, MZA, EZA, DCP and IND (24-50 nM). Among them the most potent hCA IX inhibitor 7b (K-I = 2.8 nM) was 8.5-fold stronger than IND (K-I = 24 nM). Toward tumor-associated hCA XII compounds 6c and 10a (K-I = 2.7 and 2.8 nM, respectively) showed a better inhibitory potency than reference sulfonamides MZA and IND (K-I = 3.4 nM). (C) 2014 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2014.05.039

文献信息

• Synthesis, Anticancer Evaluation and Structure-Activity Analysis of Novel (E)- 5-(2-Arylvinyl)-1,3,4-oxadiazol-2-yl)benzenesulfonamides
  作者：Krzysztof Szafrański、Jarosław Sławiński、Łukasz Tomorowicz、Anna Kawiak

  DOI：10.3390/ijms21062235

  日期：——

  displayed promising in vitro anticancer activity, we have synthesized a group of novel (E)-5-[(5-(2-arylvinyl)-1,3,4-oxadiazol-2-yl)]-4-chloro-2-R1-benzenesulfonamides 7–36 as well as (E)-4-[5-styryl1,3,4-oxadiazol-2-yl]benzenesulfonamides 47–50 and (E)-2-(2,4-dichlorophenyl)-5-(2-arylvinyl)-1,3,4-oxadiazols 51–55. All target derivatives were evaluated for their anticancer activity on HeLa, HCT-116, and MCF-7

  为了更多地了解 (E)-3-(5-苯乙烯基-1,3,4-恶二唑-2-基)苯磺酰胺衍生物的结构-活性关系，该衍生物在我们之前的研究中显示出良好的体外抗癌活性，我们有合成了一组新型 (E)-5-[(5-(2-芳基乙烯基)-1,3,4-恶二唑-2-基)]-4-氯-2-R1-苯磺酰胺 7–36 以及(E)-4-[5-苯乙烯基1,3,4-恶二唑-2-基]苯磺酰胺47–50和(E)-2-(2,4-二氯苯基)-5-(2-芳基乙烯基)-1, 3,4-恶二唑 51–55。所有目标衍生物均针对 HeLa、HCT-116 和 MCF-7 人类肿瘤细胞系的抗癌活性进行了评估。对所得结果进行分析以解释2-芳基-乙烯基取代基和苯磺酰胺支架的结构对抗肿瘤活性的影响。带有 5-硝基噻吩部分的化合物 31 对 HCT-116、MCF-7 和 HeLa 细胞系表现出最有效的抗癌活性，IC50 值分别为 0.5、4 和 4.5
• Novel 2-benzylthio-5-(1,3,4-oxadiazol-2-yl)benzenesulfonamides with anticancer activity: Synthesis, QSAR study, and metabolic stability
  作者：Jarosław Sławiński、Krzysztof Szafrański、Aneta Pogorzelska、Beata Żołnowska、Anna Kawiak、Katarzyna Macur、Mariusz Belka、Tomasz Bączek

  DOI：10.1016/j.ejmech.2017.03.039

  日期：2017.5

  A series of novel 2-benzylthio-4-chloro-5-(5-substituted 1,3,4-oxadiazol-2-yl)benzenesulfonamides (4 27) have been synthesized as potential anticancer agents. MIT assay was carried out to determine the cytotoxic activity against three human cancer cell lines: colon cancer HCT-116, breast cancer MCF-7 and cervical cancer HeLa as well as to determine the influence on human keratinocyte cell line HaCaT. Relatively high (IC50: 7-17 mu M) cytostatic activity and selectivity against HeLa cell line was found for compounds 6, 7, 9-11 and 16. While compounds 23-27 bearing styryl moieties attached to a 1,3,4-oxadiazole ring at position 5, exhibited significant activity against two and/or three cancer cell lines with IC50: 11-29 mu M. Further quantitative structure-activity relationships based on molecular descriptors calculated by DRAGON software, were investigated by Orthogonal Projections to Latent Structures (OPLS) technique and Variable Influence on Projection (VIP) analysis. Considering molecular descriptors with the highest influence on projection (highest VIP values) lipophilicity of tested compounds was pointed as main factor affecting activity towards HCT-116 cell line, while structural parameters associated with presence of styryl substituent in position 5 of 1,3,4-oxadiazole ring were identified as essential for activity towards MCF-7 breast cancer. In vitro tests for metabolic stability in the presences of pooled human liver microsomes and NADPH showed that some of the most active compounds 26 and 27 presented favorable metabolic stability with t(1/2) in the range of 28.1-36.0 min. (C) 2017 Elsevier Masson SAS. All rights reserved.
• Diuretics. 4-Substituted 3-sulfamoylbenzoic acid hydrazides
  作者：M. L. Hoefle、L. T. Blouin、H. A. DeWald、Ann Holmes、Dorothy Williams

  DOI：10.1021/jm00311a012

  日期：1968.9
• Synthesis and in vitro activity of novel 2-(benzylthio)-4-chloro-5-(1,3,4-oxadiazol-2-yl)benzenesulfonamide derivatives
  作者：Kamil Brożewicz、Jarosław Sławiński

  DOI：10.1007/s00706-012-0732-6

  日期：2012.6

  Two series of novel 4-chloro-2-(benzylthio)-5-(1,3,4-oxadiazol-2-yl)benzenesulfonamides and their -aroyl derivatives have been synthesized and evaluated for in vitro anticancer activity against the full NCI-60 cell line panel. Most of the compounds exhibited antiproliferative activity. Among them a compound bearing an -(thien-2-ylcarbonyl) moiety showed broad-spectrum activity with 50% growth inhibition (GI(50)) values in the range of 2.02-7.82 mu M over 50 cell lines..
• POMARNACKA, E.;ANGIELSKI, S.;HOPPE, A., ACTA POL. PHARM., 1984, 41, N 2, 141-151
  作者：POMARNACKA, E.、ANGIELSKI, S.、HOPPE, A.

  DOI：——

  日期：——