4-[5-(4-methoxy-phenyl)-3-thiophen-2-yl-4,5-dihydro-pyrazol-1-yl]-benzenesulfonamide | 1222182-31-1

• 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-[5-(4-methoxy-phenyl)-3-thiophen-2-yl-4,5-dihydro-pyrazol-1-yl]-benzenesulfonamide
• 英文别名: 4-(5-(4-methoxyphenyl)-3-(thiophen-2-yl)-4,5-dihydro-1H-pyrazol-1-yl)benzenesulfonamide；4-[5-(4-Methoxyphenyl)-3-(2-thienyl)-2-pyrazolin-1-yl]benzenesulfonamide；4-[3-(4-methoxyphenyl)-5-thiophen-2-yl-3,4-dihydropyrazol-2-yl]benzenesulfonamide
• CAS: 1222182-31-1
• 化学式: C₂₀H₁₉N₃O₃S₂
• 分子量: 413.521
• InChiKey: LNZYZAVDMUOOBN-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.6
• 重原子数：
  28
• 可旋转键数：
  5
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.15
• 拓扑面积：
  122
• 氢给体数：
  1
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  4-[5-(4-methoxy-phenyl)-3-thiophen-2-yl-4,5-dihydro-pyrazol-1-yl]-benzenesulfonamide 、 邻甲苯异氰酸酯 在 potassium carbonate 作用下， 以 丙酮 为溶剂， 以72.1%的产率得到{(4-[3-(thiophen-2-yl)-5-p-methoxyphenyl-4,5-dihydropyrazol-1-yl]phenyl)sulfonyl}-N'-o-tolylurea
  参考文献：
  名称：

  Novel benzenesulfonylureas containing thiophenylpyrazoline moiety as potential antidiabetic and anticancer agents

  摘要：

  In the present study a library of twenty six benzenesulfonylureas containing thiophenylpyrazoline moiety has been synthesized. All the compounds were docked against PPAR-gamma target. Most of the compounds displayed higher dock score than standard drugs, glibenclamide and rosiglitazone. All the synthesized compounds were primarily evaluated for their antidiabetic effect by oral glucose tolerance test. Further assessment of antidiabetic potential of sixteen active compounds was then done on STZ induced diabetic model. The results of in vivo activity by both the methods were found to be consistent with each other as well as with docking studies. Change in body weight of STZ induced animals post treatment was also assessed at the end of study. In vitro PPAR-gamma transactivation assay was performed on active compounds in order to validate docking results and the most active compound 3k was also shown to elevate gene expression of PPAR-gamma. Furthermore, the compounds were screened by National Cancer Institute, Bethesda for anticancer effect and two compounds 3h and 3i were selected at one dose level since they exhibited sensitivity towards tumor cell lines (mainly melanoma). (C) 2014 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2014.09.044
• 作为产物：
  描述：

  4-甲氧基苯甲醛 在 sodium hydroxide 作用下， 以 乙醇 为溶剂， 反应 12.0h， 生成 4-[5-(4-methoxy-phenyl)-3-thiophen-2-yl-4,5-dihydro-pyrazol-1-yl]-benzenesulfonamide
  参考文献：
  名称：

  Novel benzenesulfonylureas containing thiophenylpyrazoline moiety as potential antidiabetic and anticancer agents

  摘要：

  In the present study a library of twenty six benzenesulfonylureas containing thiophenylpyrazoline moiety has been synthesized. All the compounds were docked against PPAR-gamma target. Most of the compounds displayed higher dock score than standard drugs, glibenclamide and rosiglitazone. All the synthesized compounds were primarily evaluated for their antidiabetic effect by oral glucose tolerance test. Further assessment of antidiabetic potential of sixteen active compounds was then done on STZ induced diabetic model. The results of in vivo activity by both the methods were found to be consistent with each other as well as with docking studies. Change in body weight of STZ induced animals post treatment was also assessed at the end of study. In vitro PPAR-gamma transactivation assay was performed on active compounds in order to validate docking results and the most active compound 3k was also shown to elevate gene expression of PPAR-gamma. Furthermore, the compounds were screened by National Cancer Institute, Bethesda for anticancer effect and two compounds 3h and 3i were selected at one dose level since they exhibited sensitivity towards tumor cell lines (mainly melanoma). (C) 2014 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2014.09.044

文献信息

• Synthesis, molecular modeling, and biological evaluation of 4-[5-aryl-3-(thiophen-2-yl)-4,5-dihydro-1<i>H</i>-pyrazol-1-yl] benzenesulfonamides toward acetylcholinesterase, carbonic anhydrase I and II enzymes
  作者：Cem Yamali、Halise Inci Gul、Abdulilah Ece、Parham Taslimi、Ilhami Gulcin

  DOI：10.1111/cbdd.13149

  日期：2018.4

  In this study, 4‐[5‐aryl‐3‐(thiophen‐2‐yl)‐4,5‐dihydro‐1H‐pyrazol‐1‐yl] benzenesulfonamides were synthesized, and inhibition effects on AChE, hCA I, and hCA II were evaluated. Ki values of the compounds toward hCA I were in the range of 24.2 ± 4.6‐49.8 ± 12.8 nm, while they were in the range of 37.3 ± 9.0‐65.3 ± 16.7 nm toward hCA II. Ki values of the acetazolamide were 282.1 ± 19.7 nm and 103.60 ± 27

  在这项研究中，合成了4- [5-芳基-3-（噻吩-2-基）-4,5-二氢-1 H-吡唑-1-基]苯磺酰胺，并对AChE，hCA I和AChE具有抑制作用。 hCA II进行了评估。朝向hCA I的化合物的K i值在24.2±4.6-49.8±12.8 n m的范围内，而朝向hCA II的K i值在37.3±9.0-65.3±16.7 n m的范围内。两种同工酶的乙酰唑酰胺的K i值分别为282.1±19.7 n m和103.60±27.6 n m。化合物抑制的AChE与ķ我在22.7±10.3-109.1±27.0 n中的范围米，而他克林具有ķi值为66.5±13.8 n m。还进行了M06-L / 6-31 + G（d，p）// AM1水平的电子结构计算和分子对接研究，以启发抑制机理并支持实验结果。通过分子特性计算获得的结果表明，这些化合物符合药物样特性。在这项研究中获得的实验和计算结果可能有助于设计针对hCA
• Synthesis, cyclooxygenase inhibition, anti-inflammatory evaluation and ulcerogenic liability of new 1,3,5-triarylpyrazoline and 1,5-diarylpyrazole derivatives as selective COX-2 inhibitors
  作者：Khaled R.A. Abdellatif、Eman K.A. Abdelall、Wael A.A. Fadaly、Gehan M. Kamel

  DOI：10.1016/j.bmcl.2015.11.105

  日期：2016.1

  Two new series of 1,3,5-triarylpyrazolines 10a-m and 1,5-diarylpyrazoles 14a-d were synthesized. All prepared compounds were evaluated for their in vitro COX-1/COX-2 inhibitory activity and the in vivo anti-inflammatory activity. All compounds were more selective for COX-2 isozyme and showed good in vivo anti-inflammatory activity. Compound 10k was the most COX-2 selective compound (S.I. = 5.91) and the most potent anti-inflammatory derivative (ED50 = 99 mu mol/kg) which is approximately five folds more potent than ibuprofen (ED50 = 499 mu mol/kg) and had half potency of celecoxib (ED50 = 47 mu mol/kg). All compounds were less ulcerogenic (Ulcer Indexes = 1.20-5.00) than ibuprofen (Ulcer Index = 20.25) and comparable to celecoxib (Ulcer Index = 2.90). (C) 2015 Elsevier Ltd. All rights reserved.
• US9642835B2
  申请人：——

  公开号：US9642835B2

  公开（公告）日：2017-05-09
• Novel benzenesulfonylureas containing thiophenylpyrazoline moiety as potential antidiabetic and anticancer agents
  作者：Chetna Kharbanda、Mohammad Sarwar Alam、Hinna Hamid、Kalim Javed、Syed Shafi、Yakub Ali、Perwez Alam、M.A.Q. Pasha、Abhijeet Dhulap、Sameena Bano、Syed Nazreen、Saqlain Haider

  DOI：10.1016/j.bmcl.2014.09.044

  日期：2014.11

  In the present study a library of twenty six benzenesulfonylureas containing thiophenylpyrazoline moiety has been synthesized. All the compounds were docked against PPAR-gamma target. Most of the compounds displayed higher dock score than standard drugs, glibenclamide and rosiglitazone. All the synthesized compounds were primarily evaluated for their antidiabetic effect by oral glucose tolerance test. Further assessment of antidiabetic potential of sixteen active compounds was then done on STZ induced diabetic model. The results of in vivo activity by both the methods were found to be consistent with each other as well as with docking studies. Change in body weight of STZ induced animals post treatment was also assessed at the end of study. In vitro PPAR-gamma transactivation assay was performed on active compounds in order to validate docking results and the most active compound 3k was also shown to elevate gene expression of PPAR-gamma. Furthermore, the compounds were screened by National Cancer Institute, Bethesda for anticancer effect and two compounds 3h and 3i were selected at one dose level since they exhibited sensitivity towards tumor cell lines (mainly melanoma). (C) 2014 Elsevier Ltd. All rights reserved.