6-(4-methoxyphenyl)-2-(4-(aminosulfonyl)phenyl)pyridazin-3(2H)-one | 1160787-30-3

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二嗪类
• 英文名称: 6-(4-methoxyphenyl)-2-(4-(aminosulfonyl)phenyl)pyridazin-3(2H)-one
• 英文别名: 6-(4-Methoxyphenyl)-2-benzenesulfonamidepyridazine-3(2H)-one；4-[3-(4-methoxyphenyl)-6-oxopyridazin-1-yl]benzenesulfonamide
• CAS: 1160787-30-3
• 化学式: C₁₇H₁₅N₃O₄S
• 分子量: 357.39
• InChiKey: NNNPBKBKVVJHAT-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.5
• 重原子数：
  25
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.06
• 拓扑面积：
  110
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  6-(4-methoxyphenyl)-2-(4-(aminosulfonyl)phenyl)pyridazin-3(2H)-one 、 氯甲酸乙酯 在 potassium carbonate 作用下， 以 丙酮 为溶剂， 反应 18.0h， 以27.7%的产率得到ethyl ({4-[6-(4-methoxyphenyl)-3-oxopyridazin-2-yl]phenyl}sulfonyl)carbamate
  参考文献：
  名称：

  Synthesis and blood glucose lowering effect of novel pyridazinone substituted benzenesulfonylurea derivatives

  摘要：

  Fifteen novel pyridazinone substituted benzenesulfonylurea derivatives (3a-o) were synthesized from corresponding sulfonamides derivatives via novel carbamates (2a-e). These were characterized by elemental analysis and various spectroscopic methods viz. IR, H-1 NMR, C-13 NMR and MS. Blood sugar lowering effect of thirteen (3a-c, 3e, 3g-o) sulfonylurea derivatives at the dose of 20 mg/kg (p.o.) were assessed using glucose tolerance test in normal and NIDDM (n2-STZ) rat models. All compounds except 3c, 3e and 3o almost completely prevented the rise of blood glucose of NIDDM rats as compared with NIDDM control. While compounds 3c and 3o showed more than 50% prevention in the rise of blood glucose levels. in glucose-fed normal rats these compounds at the same dose except 3e significantly prevented the rise of blood glucose (more than 50%) when compared with control of glucose-fed normal rats. From the results, novel compounds (3a-c, 3g-n) exhibited considerably potent blood glucose lowering activity and may be used as lead compounds for developing new antidiabetic drugs. Some structure-activity relationship was observed while varying nature of 'Ar' and 'R'. (C) 2008 Published by Elsevier Masson SAS.

  DOI：

  10.1016/j.ejmech.2008.12.013
• 作为产物：
  描述：

  苯甲醚 在 aluminum (III) chloride 作用下， 以 乙醇 为溶剂， 反应 48.0h， 生成 6-(4-methoxyphenyl)-2-(4-(aminosulfonyl)phenyl)pyridazin-3(2H)-one
  参考文献：
  名称：

  一些新型的6-芳基-2-（对氨基磺酰基苯基）-哒嗪-3（2H）-一的合成及抗癌活性的评价

  摘要：

  通过适当的芳酰基丙烯酸和4-肼基苯磺酰胺盐酸盐在乙醇中的缩合，合成了一系列带有苯磺酰胺部分（2a - h）的新型哒嗪酮衍生物。美国国家癌症研究所评估了五种衍生物（2a，2b，2d，2g和2h）对人癌细胞的抗癌活性。在2小时显示针对SR（白血病）和NCI-H522（非小细胞肺癌）显着的活性用GI 50值小于0.1μM。它还对白血病（CCRF-CEM，HL-60（TB），K-562，MOLT-4，RPMI-8226），非小细胞肺癌（NCI-H460），结肠（HCT-116， HCT-15，HT29，KMI2，SW-620），中枢神经系统（SF-295），黑素瘤（MALME-3M，M14，MDA-MB-435 SK-MEL-5），卵巢癌（OVCAR-3，NCI / ADR- RES）和GI 50小于1.0μM的乳腺癌（MCF7）癌细胞系。2h的急性毒性研究表明，无胸腺裸鼠对腹膜内（400 mg /

  DOI：

  10.1016/j.ejmech.2012.01.026

文献信息

• Synthesis and evaluation of anticancer activity of some novel 6-aryl-2-(p-sulfamylphenyl)-pyridazin-3(2H)-ones
  作者：I.G. Rathish、Kalim Javed、Shamim Ahmad、Sameena Bano、M.S. Alam、Mymoona Akhter、K.K. Pillai、Syed Ovais、Mohammed Samim

  DOI：10.1016/j.ejmech.2012.01.026

  日期：2012.3

  condensation of appropriate aroylacrylic acid and 4-hydrazinobenzenesulfonamide hydrochloride in ethanol. Five derivatives (2a, 2b, 2d, 2g and 2h) were evaluated for their anticancer activity toward human cancer cell lines by the National Cancer Institute. The 2h showed remarkable activity against SR (leukemia) and NCI-H522 (non-small cell lung) with a GI50 value of less than 0.1 μM. It also displayed

  通过适当的芳酰基丙烯酸和4-肼基苯磺酰胺盐酸盐在乙醇中的缩合，合成了一系列带有苯磺酰胺部分（2a - h）的新型哒嗪酮衍生物。美国国家癌症研究所评估了五种衍生物（2a，2b，2d，2g和2h）对人癌细胞的抗癌活性。在2小时显示针对SR（白血病）和NCI-H522（非小细胞肺癌）显着的活性用GI 50值小于0.1μM。它还对白血病（CCRF-CEM，HL-60（TB），K-562，MOLT-4，RPMI-8226），非小细胞肺癌（NCI-H460），结肠（HCT-116， HCT-15，HT29，KMI2，SW-620），中枢神经系统（SF-295），黑素瘤（MALME-3M，M14，MDA-MB-435 SK-MEL-5），卵巢癌（OVCAR-3，NCI / ADR- RES）和GI 50小于1.0μM的乳腺癌（MCF7）癌细胞系。2h的急性毒性研究表明，无胸腺裸鼠对腹膜内（400 mg /
• Synthesis and blood glucose lowering effect of novel pyridazinone substituted benzenesulfonylurea derivatives
  作者：I.G. Rathish、Kalim Javed、Sameena Bano、Shamim Ahmad、M.S. Alam、K.K. Pillai

  DOI：10.1016/j.ejmech.2008.12.013

  日期：2009.6

  Fifteen novel pyridazinone substituted benzenesulfonylurea derivatives (3a-o) were synthesized from corresponding sulfonamides derivatives via novel carbamates (2a-e). These were characterized by elemental analysis and various spectroscopic methods viz. IR, H-1 NMR, C-13 NMR and MS. Blood sugar lowering effect of thirteen (3a-c, 3e, 3g-o) sulfonylurea derivatives at the dose of 20 mg/kg (p.o.) were assessed using glucose tolerance test in normal and NIDDM (n2-STZ) rat models. All compounds except 3c, 3e and 3o almost completely prevented the rise of blood glucose of NIDDM rats as compared with NIDDM control. While compounds 3c and 3o showed more than 50% prevention in the rise of blood glucose levels. in glucose-fed normal rats these compounds at the same dose except 3e significantly prevented the rise of blood glucose (more than 50%) when compared with control of glucose-fed normal rats. From the results, novel compounds (3a-c, 3g-n) exhibited considerably potent blood glucose lowering activity and may be used as lead compounds for developing new antidiabetic drugs. Some structure-activity relationship was observed while varying nature of 'Ar' and 'R'. (C) 2008 Published by Elsevier Masson SAS.