4-(3-oxo-cyclohex-1-enylamino)benzenesulfonamide | 92959-60-9

• 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-(3-oxo-cyclohex-1-enylamino)benzenesulfonamide
• 英文别名: 4-(3-oxocyclohex-1-enylamino)benzenesulfonamide；4-(3-oxocyclohexenylamino)benzenesulfonamide；1-(N⁴-Sulfanilamido)-cyclohexen-(1)-on-(3)；4-[(3-Oxocyclohexen-1-yl)amino]benzenesulfonamide
• CAS: 92959-60-9
• 化学式: C₁₂H₁₄N₂O₃S
• 分子量: 266.321
• InChiKey: VJEVBQILZPDIPH-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.7
• 重原子数：
  18
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  97.6
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  4-(3-oxo-cyclohex-1-enylamino)benzenesulfonamide 在 溶剂黄146 、 三乙胺 作用下， 以 乙醇 为溶剂， 反应 11.0h， 生成 4-(3-cyano-2-(2,4-dichlorobenzylideneamino)-4-(2,4-dichlorophenyl)-5-oxo-5,6,7,8-tetrahydroquinolin-1(4H)-yl)benzenesulfonamide
  参考文献：
  名称：

  一些新型杂环磺酰胺衍生物的体外细胞毒性评估

  摘要：

  带有磺酰胺的化合物具有多种生物活性，最近有报道显示其在体外和/或体内具有显着的抗肿瘤活性。抗癌活性的机制多种多样，最主要的机制是抑制碳酸酐酶同工酶。这项工作报告了一些新的喹啉，嘧啶[4,5- b ]喹啉和带有磺酰胺部分的3,1-恶嗪基喹啉衍生物的合成。评价所有新合成的化合物对艾氏腹水癌细胞的体外抗癌活性。化合物10，13，和26分别与IC最活跃的化合物50个6.1μ值中号，6.8μ中号，和6.4μ中号，分别与显示出比参考药物阿霉素更好的活性（IC 50 = 68.1μ中号）。J.杂环化​​学.2011。

  DOI：

  10.1002/jhet.619
• 作为产物：
  描述：

  1,3-环己二酮 、 磺胺 以 乙醇 为溶剂， 反应 3.0h， 以92%的产率得到4-(3-oxo-cyclohex-1-enylamino)benzenesulfonamide
  参考文献：
  名称：

  发现一些具有生物活性磺酰胺部分的新型四氢喹啉衍生物作为一类新的抗肿瘤药

  摘要：

  本文介绍了一些新型的4-（2-氨基-3-氰基-4-（取代的芳基）-5-氧代-5,6,7,8-四氢喹啉-1（4H）-基）苯磺酰胺的合成（23 - 41）开始与4-（3-氧代-环己-1-烯基氨基）苯磺酰胺（3）。评价所有新合成的化合物的体外抗肿瘤活性。化合物32，25，41，35，33，和37与IC 50个值（2.5，3，5，10，12，和12.5微克/毫升）是更有效的和多柔比星相比（CAS-23214-92-8）有效作为参考药物与（IC 50值= 37.5μg/ mL）。另外，化合物28，30，31，和34（用IC 50个值= 25微克/毫升）几乎作为活性如多柔比星。

  DOI：

  10.1016/j.ejmech.2010.01.022

文献信息

• Synthesis and in vitro anticancer evaluation of some novel hexahydroquinoline derivatives having a benzenesulfonamide moiety
  作者：Mansour S. Al-Said、Mostafa M. Ghorab、Mohammed S. Al-Dosari、Mostafa M. Hamed

  DOI：10.1016/j.ejmech.2010.11.002

  日期：2011.1

  to have a role in the treatment of cancer. Several sulfonamide compounds bearing an aromatic or a heteroaromatic ring were found to posses potent carbonic anhydrase inhibitory activity and so can be used in the treatment of several types of cancer. In this paper, we present the synthesis of some novel quinoline 7–13, 21–26, 28 and pyrimidoquinoline 14–18, 20, 27 derivatives having a sulfonamide moiety

  已经发现抑制碳酸酐酶同工酶在癌症的治疗中具有作用。已发现几种带有芳族或杂芳族环的磺酰胺化合物具有有效的碳酸酐酶抑制活性，因此可用于治疗多种类型的癌症。在本文中，我们提出了一些新颖的喹啉的合成7 - 13，21 - 26，28和pyrimidoquinoline 14 - 18，20，27层具有一个磺酰胺部分的衍生物。对所有新合成的化合物进行了体外评估抗癌活性。与使用的参考药物相比，几种化合物表现出令人感兴趣的细胞毒性活性。另外，进行了合成化合物对接至碳酸酐酶同工酶II（CA II）活性位点的研究，以便对所提出的作用机理提出建议。
• Novel quinolines and pyrimido[4,5-b]quinolines bearing biologically active sulfonamide moiety as a new class of antitumor agents
  作者：Saleh I. Alqasoumi、Areej M. Al-Taweel、Ahmed M. Alafeefy、Eman Noaman、Mostafa M. Ghorab

  DOI：10.1016/j.ejmech.2009.11.021

  日期：2010.2

  Some novel quinolines and pyrimido[4,5-b]quinolines have been synthesized. The structures of which were confirmed by elemental analyses and spectral data. All the target compounds were subjected to in-vitro antitumor activity against Ehrlich Ascites Carcinoma (EAC) cells. Compounds 24, 19 and 12 showed higher activity with IC50 values (5.5, 6.9, 7 μg/ml) when compared with Doxorubicin as a reference

  已经合成了一些新颖的喹啉和嘧啶并[4,5-b]喹啉。其结构已通过元素分析和光谱数据证实。所有目标化合物均对艾氏腹水癌（EAC）细胞具有体外抗肿瘤活性。化合物24，19和12显示出更高的活性，IC 50值（5.5，6.9，7微克/毫升），当多柔比星作为参照药物（IC相比50值38微克/毫升）。
• Discovering some novel tetrahydroquinoline derivatives bearing the biologically active sulfonamide moiety as a new class of antitumor agents
  作者：Saleh I. Alqasoumi、Areej M. Al-Taweel、Ahmed M. Alafeefy、Mostafa M. Ghorab、Eman Noaman

  DOI：10.1016/j.ejmech.2010.01.022

  日期：2010.5

  5 μg/mL) are more potent and efficacious than Doxorubicin (CAS-23214-92-8) as reference drug with (IC50 value = 37.5 μg/mL). Also, compounds 28, 30, 31, and 34 (with IC50 values = 25 μg/mL) are nearly as active as Doxorubicin.

  本文介绍了一些新型的4-（2-氨基-3-氰基-4-（取代的芳基）-5-氧代-5,6,7,8-四氢喹啉-1（4H）-基）苯磺酰胺的合成（23 - 41）开始与4-（3-氧代-环己-1-烯基氨基）苯磺酰胺（3）。评价所有新合成的化合物的体外抗肿瘤活性。化合物32，25，41，35，33，和37与IC 50个值（2.5，3，5，10，12，和12.5微克/毫升）是更有效的和多柔比星相比（CAS-23214-92-8）有效作为参考药物与（IC 50值= 37.5μg/ mL）。另外，化合物28，30，31，和34（用IC 50个值= 25微克/毫升）几乎作为活性如多柔比星。
• Design, synthesis, and antitumor screening of certain novel tetrahydroquinoline sulfonamides
  作者：Ahmed M. Alafeefy

  DOI：10.3109/14756366.2014.899595

  日期：2015.3.4

  Sulfonamide containing molecules are of sound biomedical interest. This work comprises the synthesis and in vitro antitumor testing of new library of 20 such molecules. These compounds were screened for cytotoxic activity against three tumor cell lines MCF-7, HeLa, and HepG2 using MTT assay. The yield was low but all the target compounds exhibited antiproliferative activity better than the standard drug Doxorubicin (CAS-23214-92-8). Seven compounds were more potent and four compounds were as active as the standard drug. There were no great difference between compounds obtained from dimedone and those obtained from cyclohexandione. Also no significant difference found in activity between compounds bearing o-amino ethyl ester side chain and compounds bearing o-amino amide derivatives. However, compounds bearing o-amino-cyano group, although retained considerable activity they were far less active than the preceding two. It was clear that monohydroxy aldehyde derivatives were less active compared with the di and trihydroxy ones.
• In vitro cytotoxic evaluation of some new heterocyclic sulfonamide derivatives
  作者：Mostafa M. Ghorab、Mansour S. Al-Said、Ebaa M. El-Hossary

  DOI：10.1002/jhet.619

  日期：2011.5

  many types of biological activities and have been recently reported to show substantial antitumor activity in vitro and/or in vivo. There are a variety of mechanisms for the anticancer activity, and the most prominent mechanism is the inhibition of carbonic anhydrase isozymes. This work reports the synthesis of some new quinoline, pyrimido[4,5‐b]quinoline and 3,1‐oxazinoquinoline derivatives bearing a

  带有磺酰胺的化合物具有多种生物活性，最近有报道显示其在体外和/或体内具有显着的抗肿瘤活性。抗癌活性的机制多种多样，最主要的机制是抑制碳酸酐酶同工酶。这项工作报告了一些新的喹啉，嘧啶[4,5- b ]喹啉和带有磺酰胺部分的3,1-恶嗪基喹啉衍生物的合成。评价所有新合成的化合物对艾氏腹水癌细胞的体外抗癌活性。化合物10，13，和26分别与IC最活跃的化合物50个6.1μ值中号，6.8μ中号，和6.4μ中号，分别与显示出比参考药物阿霉素更好的活性（IC 50 = 68.1μ中号）。J.杂环化​​学.2011。