6-{[(4-fluorophenyl)sulfonyl]amino}-2-methyl-3-vinylbenzoic acid | 681241-98-5

• 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: 6-{[(4-fluorophenyl)sulfonyl]amino}-2-methyl-3-vinylbenzoic acid
• 英文别名: 5,6-Disubstituted anthranilic acid sulfonamide, 9b；3-ethenyl-6-[(4-fluorophenyl)sulfonylamino]-2-methylbenzoic acid
• CAS: 681241-98-5
• 化学式: C₁₆H₁₄FNO₄S
• 分子量: 335.356
• InChiKey: GAPRZMDRSXTQPM-UHFFFAOYSA-N

物化性质

• 沸点：
  501.4±60.0 °C(Predicted)
• 密度：
  1.411±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.8
• 重原子数：
  23
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.06
• 拓扑面积：
  91.8
• 氢给体数：
  2
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  6-{[(4-fluorophenyl)sulfonyl]amino}-2-methyl-3-vinylbenzoic acid 在 四氧化锇 水 、 N-甲基吗啉氧化物 作用下， 以 四氢呋喃 、 水 、 叔丁醇 为溶剂， 反应 4.0h， 以43.5%的产率得到3-[1,2-dihydroxyethyl]-6-{[(4-fluorophenyl)sulfonyl]amino}-2-methylbenzoic acid
  参考文献：
  名称：

  Sulfonamides having antiangiogenic and anticancer activity

  摘要：

  描述了具有蛋氨酸氨基肽酶-2抑制剂（MetAP2）的化合物。还描述了包括这些化合物的药物组合物、使用这些化合物的治疗方法、抑制血管生成的方法以及治疗癌症的方法。

  公开号：

  US20040167128A1
• 作为产物：
  描述：

  6-氨基-3-溴-2-甲基苯甲酸甲酯 在 四(三苯基膦)钯 吡啶 、 lithium hydroxide 、 cesium fluoride 作用下， 以 1,4-二氧六环 、 甲醇 、 乙二醇二甲醚 、 二氯甲烷 为溶剂， 反应 0.33h， 生成 6-{[(4-fluorophenyl)sulfonyl]amino}-2-methyl-3-vinylbenzoic acid
  参考文献：
  名称：

  Lead optimization of methionine aminopeptidase-2 (MetAP2) inhibitors containing sulfonamides of 5,6-disubstituted anthranilic acids

  摘要：

  A series of aryl sulfonamides of 5,6-disubstituted anthranilic acids were identified as potent inhibitors of methionine aminopeptidase-2 (MetAP2). Small alkyl groups and 3-furyl were tolerated at the 5-position of anthranilic acid, while -OCH3, CH3, and Cl were found optimal for the 6-position. Placement of 2-aminoethoxy group at the 6-position enabled interaction with the second Mn2+ but did not result in enhancement in potency. Introduction of a tertiary amino moiety at the ortho-position of the sulfonyl phenyl ring gave reduced protein binding and improved cellular activity, but led to lower oral bioavailability. (c) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2007.02.062

文献信息

• [EN] SULFONAMIDES HAVING ANTIANGIOGENIC AND ANTICANCER ACTIVITY<br/>[FR] SULFONAMIDES AYANT UNE ACTIVITE ANTI-ANGIOGENIQUE ET ANTICANCEREUSE
  申请人：ABBOTT LAB

  公开号：WO2004033419A1

  公开（公告）日：2004-04-22

  Compounds having methionine aminopeptidase-2 inhibitory (MetAP2) are described. Also described are pharmaceutical compositions comprising the compounds, methods of treatment using the compounds, methods of inhibiting angiogenesis, and methods of treating cancer.

  描述了具有甲硫氨酸氨肽酶-2（MetAP2）抑制剂的化合物。还描述了包含这些化合物的制药组合物，使用这些化合物进行治疗的方法，抑制血管生成的方法以及治疗癌症的方法。
• SULFONAMIDES HAVING ANTIANGIOGENIC AND ANTICANCER ACTIVITY
  申请人：Abbott Laboratories

  公开号：EP1549613A1

  公开（公告）日：2005-07-06
• US7491718B2
  申请人：——

  公开号：US7491718B2

  公开（公告）日：2009-02-17
• Sulfonamides having antiangiogenic and anticancer activity
  申请人：——

  公开号：US20040157836A1

  公开（公告）日：2004-08-12

  Compounds having methionine aminopeptidase-2 inhibitory (MetAP2) are described. Also described are pharmaceutical compositions comprising the compounds, methods of treatment using the compounds, methods of inhibiting angiogenesis, and methods of treating cancer.

  描述了具有蛋氨酸氨基肽酶-2抑制剂（MetAP2）的化合物。还描述了包括这些化合物的药物组合物、使用这些化合物的治疗方法、抑制血管生成的方法以及治疗癌症的方法。
• Lead optimization of methionine aminopeptidase-2 (MetAP2) inhibitors containing sulfonamides of 5,6-disubstituted anthranilic acids
  作者：Gary T. Wang、Robert A. Mantei、Megumi Kawai、Jason S. Tedrow、David M. Barnes、Jieyi Wang、Qian Zhang、Pingping Lou、Lora A. Garcia、Jennifer Bouska、Melinda Yates、Chang Park、Russell A. Judge、Richard Lesniewski、George S. Sheppard、Randy L. Bell

  DOI：10.1016/j.bmcl.2007.02.062

  日期：2007.5

  A series of aryl sulfonamides of 5,6-disubstituted anthranilic acids were identified as potent inhibitors of methionine aminopeptidase-2 (MetAP2). Small alkyl groups and 3-furyl were tolerated at the 5-position of anthranilic acid, while -OCH3, CH3, and Cl were found optimal for the 6-position. Placement of 2-aminoethoxy group at the 6-position enabled interaction with the second Mn2+ but did not result in enhancement in potency. Introduction of a tertiary amino moiety at the ortho-position of the sulfonyl phenyl ring gave reduced protein binding and improved cellular activity, but led to lower oral bioavailability. (c) 2007 Elsevier Ltd. All rights reserved.