methyl 4-[3-(1,3-dioxo-2,3-dihydro-1H-isoindol-2-yl)propoxy]benzoate | 773875-80-2

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 异吲哚及其衍生物
• 英文名称: methyl 4-[3-(1,3-dioxo-2,3-dihydro-1H-isoindol-2-yl)propoxy]benzoate
• 英文别名: methyl 4-(3-(1,3-dioxoisoindolin-2-yl)propoxy)benzoate；methyl 4-(3-phthalimidopropoxy)benzoate；Methyl 4-[3-(1,3-dioxoisoindol-2-yl)propoxy]benzoate
• CAS: 773875-80-2
• 化学式: C₁₉H₁₇NO₅
• 分子量: 339.348
• InChiKey: DKIZCEGYJWKZQE-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.4
• 重原子数：
  25
• 可旋转键数：
  7
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.21
• 拓扑面积：
  72.9
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  methyl 4-[3-(1,3-dioxo-2,3-dihydro-1H-isoindol-2-yl)propoxy]benzoate 在 benzotriazol-1-yloxyl-tris-(pyrrolidino)-phosphonium hexafluorophosphate 、 一水合肼 作用下， 以 乙醇 、 N,N-二甲基甲酰胺 为溶剂， 反应 7.5h， 生成 methyl 4-[3-[[(8S,9S,10R,11S,13S,14S,17R)-11,17-dihydroxy-10,13-dimethyl-3-oxo-7,8,9,11,12,14,15,16-octahydro-6H-cyclopenta[a]phenanthrene-17-carbonyl]amino]propoxy]benzoate
  参考文献：
  名称：

  [EN] SELECTIVE GLUCOCORTICOID RECEPTOR LIGANDS
  [FR] LIGANDS SÉLECTIFS DES RÉCEPTEURS DES GLUCOCORTICOÏDES

  摘要：

  公开号：

  WO2015071657A9
• 作为产物：
  描述：

  N-(3-溴丙基)苯二胺 、 对羟基苯甲酸甲酯 在 sodium hydride 作用下， 以 二甲基亚砜 、 mineral oil 为溶剂， 反应 73.0h， 以89.3%的产率得到methyl 4-[3-(1,3-dioxo-2,3-dihydro-1H-isoindol-2-yl)propoxy]benzoate
  参考文献：
  名称：

  Structural Studies of Pterin-Based Inhibitors of Dihydropteroate Synthase

  摘要：

  Dihydropteroate synthase (DHPS) is a key enzyme in bacterial folate synthesis and the target of the sulfonamide class of antibacterials. Resistance and toxicities associated with sulfonamides have led to a decrease in their clinical use. Compounds that bind to the pterin binding site of DHPS, as opposed to the p-amino benzoic acid (pABA) binding site targeted by the sulfonamide agents, arc anticipated to bypass sulfonamide resistance. To identify such inhibitors and map the pterin binding pocket, we have performed virtual screening, synthetic, and Structural studies using Bacillus anthracis DHPS. Several compounds with inhibitory activity have been identified, and Crystal Structures have been determined that show how the compounds engage the pterin site. The structural Studies identify the key binding elements and have been used to generate a structure-activity based pharmacophore map that will facilitate the development of the next generation or DHPS inhibitors which specifically target the pterin site.

  DOI：

  10.1021/jm900861d

文献信息

• Synthesis and activities of new arylsulfonamido thromboxane A2 receptor antagonists
  作者：E Sartori、F Camy、JM Teulon、F Caussade、A Virone-Oddos、A Cloarec

  DOI：10.1016/0223-5234(93)90093-t

  日期：1993.1

  New benzoic, benzeneacetic and thiazole-4-acetic acids bearing an arylsulfonamido alkyl or alkylhetero side chain were synthesized and tested in vitro for affinity for human platelet thromboxane A2 receptors and inhibition of U46619-induced rat aortic ring contraction. Influence of substitution patterns, chain length and presence of heteroatoms were studied and compounds within a 30 nmol range for inhibition of U46619-induced contractions were found. One of the most potent, 2-[(4-chloro-benzenesulfonylamino-ethyl)thio] thiazole-4-acetic acid (VII-4) was orally active (1 mg/kg), as evidenced by the inhibition of U46619-induced platelet aggregation in guinea pigs, ex vivo.
• Sartori E., Camy F., Teulon J. M., Caussade F., Virone-Oddos A., Cloarec +, Eur. J. Med. Chem, 28 (1993) N 7-8, S 625-632
  作者：Sartori E., Camy F., Teulon J. M., Caussade F., Virone-Oddos A., Cloarec +

  DOI：——

  日期：——
• SELECTIVE GLUCOCORTICOID RECEPTOR LIGANDS
  申请人：The University Of Manchester

  公开号：EP3068790A1

  公开（公告）日：2016-09-21
• [EN] SELECTIVE GLUCOCORTICOID RECEPTOR LIGANDS<br/>[FR] LIGANDS SÉLECTIFS DES RÉCEPTEURS DES GLUCOCORTICOÏDES
  申请人：UNIV MANCHESTER

  公开号：WO2015071657A9

  公开（公告）日：2016-09-15
• Structural Studies of Pterin-Based Inhibitors of Dihydropteroate Synthase
  作者：Kirk E. Hevener、Mi-Kyung Yun、Jianjun Qi、Iain D. Kerr、Kerim Babaoglu、Julian G. Hurdle、Kanya Balakrishna、Stephen W. White、Richard E. Lee

  DOI：10.1021/jm900861d

  日期：2010.1.14

  Dihydropteroate synthase (DHPS) is a key enzyme in bacterial folate synthesis and the target of the sulfonamide class of antibacterials. Resistance and toxicities associated with sulfonamides have led to a decrease in their clinical use. Compounds that bind to the pterin binding site of DHPS, as opposed to the p-amino benzoic acid (pABA) binding site targeted by the sulfonamide agents, arc anticipated to bypass sulfonamide resistance. To identify such inhibitors and map the pterin binding pocket, we have performed virtual screening, synthetic, and Structural studies using Bacillus anthracis DHPS. Several compounds with inhibitory activity have been identified, and Crystal Structures have been determined that show how the compounds engage the pterin site. The structural Studies identify the key binding elements and have been used to generate a structure-activity based pharmacophore map that will facilitate the development of the next generation or DHPS inhibitors which specifically target the pterin site.