4-[3-(4-ethoxyphenyl)-6-oxopyridazin-1(6H)-yl]benzenesulfonamide

• 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: 4-[3-(4-ethoxyphenyl)-6-oxopyridazin-1(6H)-yl]benzenesulfonamide
• 英文别名: 4-[3-(4-Ethoxyphenyl)-6-oxopyridazin-1-yl]benzenesulfonamide；4-[3-(4-ethoxyphenyl)-6-oxopyridazin-1-yl]benzenesulfonamide
• 化学式: C₁₈H₁₇N₃O₄S
• 分子量: 371.417
• InChiKey: XYEWQCLAORPMAF-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.9
• 重原子数：
  26
• 可旋转键数：
  5
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.11
• 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：

  4-[3-(4-ethoxyphenyl)-6-oxopyridazin-1(6H)-yl]benzenesulfonamide 、 4-甲基环己基异氰酸酯 在 potassium carbonate 作用下， 以 丙酮 为溶剂， 以49%的产率得到3-{4-[3-(4-ethoxyphenyl)-6-oxopyridazin-1-yl]benzenesulphonyl}-1-(4-methylcyclohexyl)urea
  参考文献：
  名称：

  设计和合成哒嗪酮取代的苯磺酰脲衍生物，作为抗高血糖药和醛糖还原酶（一种涉及糖尿病并发症的酶）的抑制剂。

  摘要：

  合成了三十种新的芳基-哒嗪酮取代的苯磺酰脲衍生物（I-XXX），并评价了在高血糖正常大鼠中的抗高血糖活性。与标准品相比，二十三种化合物（III-XI，XIV-XVII，XIX-XXIV，XXVI和XXVIII-XXX）的曲线下面积（AUC）减少百分比（从21.9％到35.5％）显示出更多或可比较的面积。药物格列齐特（22.0％）。根据对接结果，筛选了18种化合物在体外抑制大鼠晶状体醛糖还原酶的能力。十种化合物（III-VI，XII，XVI-XVIII，XXI和XXVII）显示ARI活性，IC50为34至242μM。其中，两种化合物IV和V显示出最佳的ARI活性，与槲皮素相当。因此，

  DOI：

  10.3109/14756366.2016.1142986
• 作为产物：
  描述：

  苯乙醚 在 aluminum (III) chloride 作用下， 以 乙醇 、 1,1,2,2-四氯乙烷 为溶剂， 反应 48.0h， 生成 4-[3-(4-ethoxyphenyl)-6-oxopyridazin-1(6H)-yl]benzenesulfonamide
  参考文献：
  名称：

  Pyridazinone substituted benzenesulfonamides as potent carbonic anhydrase inhibitors

  摘要：

  A series of sulfonamide derivatives (2a-l) incorporating substituted pyridazinone moieties were investigated for the inhibition of two human cytosolic carbonic anhydrase isoforms, hCA I and hCA II. All these compounds, together with the clinically used sulfonamide acetazolamide were investigated as inhibitors of the physiologically relevant isozymes I and II. These sulfonamides showed very strong inhibition against all these isoforms with K-I's in the range of 0.98-8.5 nM which makes such molecules possible to be used as leads for discovery of novel effective CA inhibitors targeting other isoforms with medicinal chemistry applications. (C) 2016 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2015.12.016

文献信息

• Pyridazinone substituted benzenesulfonamides as potent carbonic anhydrase inhibitors
  作者：Raed Yaseen、Deniz Ekinci、Murat Senturk、Alhamzah Dh. Hameed、Syed Ovais、Pooja Rathore、Mohammed Samim、Kalim Javed、Claudiu T. Supuran

  DOI：10.1016/j.bmcl.2015.12.016

  日期：2016.2

  A series of sulfonamide derivatives (2a-l) incorporating substituted pyridazinone moieties were investigated for the inhibition of two human cytosolic carbonic anhydrase isoforms, hCA I and hCA II. All these compounds, together with the clinically used sulfonamide acetazolamide were investigated as inhibitors of the physiologically relevant isozymes I and II. These sulfonamides showed very strong inhibition against all these isoforms with K-I's in the range of 0.98-8.5 nM which makes such molecules possible to be used as leads for discovery of novel effective CA inhibitors targeting other isoforms with medicinal chemistry applications. (C) 2016 Elsevier Ltd. All rights reserved.
• Design and synthesis of pyridazinone-substituted benzenesulphonylurea derivatives as anti-hyperglycaemic agents and inhibitors of aldose reductase – an enzyme embroiled in diabetic complications
  作者：Raed Yaseen、H. Pushpalatha、G. Bhanuprakash Reddy、Ameer Ismael、Ayad Ahmed、Alhamza Dheyaa、Syed Ovais、Pooja Rathore、Mohammed Samim、Mymoona Akthar、Kalicharan Sharma、Syed Shafi、Surender Singh、Kalim Javed

  DOI：10.3109/14756366.2016.1142986

  日期：2016.11.1

  vitro ability to inhibit rat lens aldose reductase. Ten compounds (III-VI, XII, XVI-XVIII, XXI and XXVII) showed ARI activity with IC50 ranging from 34 to 242 μM. Out of these, two compounds IV and V showed best ARI activity which is comparable with that of quercetin. As a result, two compounds (IV and V) possessing significant dual action (anti-hyperglycaemic and aldose reductase inhibition) were

  合成了三十种新的芳基-哒嗪酮取代的苯磺酰脲衍生物（I-XXX），并评价了在高血糖正常大鼠中的抗高血糖活性。与标准品相比，二十三种化合物（III-XI，XIV-XVII，XIX-XXIV，XXVI和XXVIII-XXX）的曲线下面积（AUC）减少百分比（从21.9％到35.5％）显示出更多或可比较的面积。药物格列齐特（22.0％）。根据对接结果，筛选了18种化合物在体外抑制大鼠晶状体醛糖还原酶的能力。十种化合物（III-VI，XII，XVI-XVIII，XXI和XXVII）显示ARI活性，IC50为34至242μM。其中，两种化合物IV和V显示出最佳的ARI活性，与槲皮素相当。因此，