4-chloro-N-(chloroacetyl)benzenesulfonamide | 38994-86-4

• 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: 4-chloro-N-(chloroacetyl)benzenesulfonamide
• 英文别名: chloroacetyl-(4-chloro-benzenesulfonyl)-amine；Chloracetyl-(4-chlor-benzolsulfonyl)-amin；2-Chloro-N-(4-chlorobenzenesulfonyl)acetamide；2-chloro-N-(4-chlorophenyl)sulfonylacetamide
• CAS: 38994-86-4
• 化学式: C₈H₇Cl₂NO₃S
• mdl: MFCD00728380
• 分子量: 268.12
• InChiKey: AEDITMBSCXEORZ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2
• 重原子数：
  15
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.125
• 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：

  4-methoxy-3-pyridinesulfonamide 、 4-chloro-N-(chloroacetyl)benzenesulfonamide 以 乙腈 为溶剂， 反应 85.0h， 以77%的产率得到1-[(4-chlorobenzenesulfonamidocarbonyl)methyl]-1,4-dihydro-4-oxo-3-pyridinesulfonamide
  参考文献：
  名称：

  Carbonic anhydrase inhibitors. Regioselective synthesis of novel series 1-substituted 1,4-dihydro-4-oxo-3-pyridinesulfonamides and their inhibition of the human cytosolic isozymes I and II and transmembrane cancer-associated isozymes IX and XII

  摘要：

  A series of novel 1-substituted 1,4-dihydro-4-oxo-3-pyridinesulfonamides 4-6, 9-17 and 21-31 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 cancer-associated isozymes CA IX and XII. Against the human isozymes hCA I the new compounds showed K(I)s in the range of 224-4830 nM, whereas toward hCA II, K(I)s = 318-873 nM. Isozyme hCA IX was inhibited with K(I)s = 11.8-93.4 nM, and hCA XII with 23.5 -82.3 nM. Compounds 12-14, 27 and 29-31 have an activity against hCA I (K(I)s = 224-889 nM) which is comparable to the clinically used sulfonamide DCP (K(I)s = 1200 nM). Several of new compounds, including 9, 10, 21, 24, 26-28 and 30 have an activity against hCA IX (K(I)s = 11.8-38.6 nM) which is comparable or more effective than the clinically used sulfonamides AAZ, MZA, EZA, DCP and IND (K(I)s = 24-50 nM). Compounds 9, 10, 13, 21-23, 26 and 27 were also very effective hCA XII inhibitors, with inhibition constants ranged from 23.5 to 47.2 nM comparable or more effective than sulfonamides EZA (K(I)s = 22 nM) or DCP (K(I)s = 50 nM), respectively. (C) 2012 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2012.08.006
• 作为产物：
  描述：

  4-氯苯磺酰胺 、 氯乙酰氯 在 正己烷 作用下， 反应 22.0h， 生成 4-chloro-N-(chloroacetyl)benzenesulfonamide
  参考文献：
  名称：

  N-Acylsulfonamide herbicidal antidotes

  摘要：

  本文描述了由硫代氨基甲酸酯或卤代乙酰胺类除草剂和与以下式对应的N-酰基磺酰胺化合物的解毒效果有效量组成的除草剂组合物：##STR1## 其中R从由氢、甲基、氯、乙酰胺和1-4碳烷氧基组成的群体中选择；R.sub.1从由氢、烯丙基和金属离子组成的群体中选择；R.sub.2从由1-10碳烷基、1-4碳卤代烷基、2-4碳烯基、2-4碳卤代烯基、丙酮基、1-6碳烷氧基、1-4碳烷氧羰基、1-4碳烷基硫代烷基、烷氧基烷基、O，O-二烷基磷酸二硫酰基烷基、苯基、卤代苯基、卤代苯基硫代烷基、环己酮二酮和二甲基巴比妥酸组成的群体中选择；或R.sub.1和R.sub.2与R.sub.2附着的羰基一起从由琥珀酰亚胺、取代琥珀酰亚胺、邻苯二甲酰亚胺和取代邻苯二甲酰亚胺组成的群体中选择。

  公开号：

  US04347380A1

文献信息

• N-Acylsulfonamide herbicidal antidotes
  申请人：Stauffer Chemical Co.

  公开号：US04495365A1

  公开（公告）日：1985-01-22

  Described herein are herbicidal compositions comprised of a thiocarbamate or haloacetanilide herbicide and an antidotally effective amount of an N-acylsulfonamide compound corresponding to the formula ##STR1## in which R is selected from the group consisting of hydrogen, methyl, chloro, acetamido, and 1-4 carbon alkoxyamido; R.sub.1 is selected from the group consisting of hydrogen, allyl, and metal ion; R.sub.2 is selected from the group consisting of 1-10 carbon alkyl, 1-4 carbon haloalkyl, 2-4 carbon alkenyl, 2-4 carbon haloalkenyl, acetonyl, 1-6 carbon alkoxy, 1-4 carbon alkoxycarbonyl, 1-4 carbon alkylthioalkyl, alkoxyalkyl, O,O-dialkylphosphorodithioylalkyl, phenyl, halophenyl, halophenylthioalkyl, cyclohexanedione, and dimethyl barbituric acid; or R.sub.1 and R.sub.2 together with the carbonyl group to which R.sub.2 is attached are selected from the group consisting of succinimide, substituted succinimide, phthalimide, and substituted phthalimide.

  本文描述了由一种硫代氨基甲酸酯或卤代乙酰胺除草剂和一种与之相对应的N-酰基磺酰胺化合物的解毒有效量组成的除草剂组合物，该化合物符合以下式子：##STR1## 其中R从氢、甲基、氯、乙酰胺和1-4碳基的烷氧基氨基中选择；R.sub.1从氢、丙烯基和金属离子中选择；R.sub.2从1-10碳基的烷基、1-4碳基的卤代烷基、2-4碳基的烯基、2-4碳基的卤代烯基、丙酮基、1-6碳基的烷氧基、1-4碳基的烷氧羰基、1-4碳基的烷硫基烷基、烷氧基烷基、O，O-二烷基磷酸二硫酰基烷基、苯基、卤代苯基、卤代苯基硫代烷基、环己二酮和二甲基巴比妥酸中选择；或R.sub.1和R.sub.2与R.sub.2附着的羰基一起从丁二酰亚胺、取代丁二酰亚胺、邻苯二甲酰亚胺和取代邻苯二甲酰亚胺中选择。
• Kretow; Kremlew, Ukrainskij Khimicheskij Zhurnal, 1959, vol. 25, p. 482
  作者：Kretow、Kremlew

  DOI：——

  日期：——
• US4266078A
  申请人：——

  公开号：US4266078A

  公开（公告）日：1981-05-05
• US4347380A
  申请人：——

  公开号：US4347380A

  公开（公告）日：1982-08-31
• US4495365A
  申请人：——

  公开号：US4495365A

  公开（公告）日：1985-01-22