N1-{3-methoxy-4-(N-methyl-5-nitro-1H-3-indolyl)methylbenzoyl}-2-methyl-1-benzenesulfonamide

• 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: N1-{3-methoxy-4-(N-methyl-5-nitro-1H-3-indolyl)methylbenzoyl}-2-methyl-1-benzenesulfonamide
• 英文别名: 3-methoxy-4-[(1-methyl-5-nitroindol-3-yl)methyl]-N-(2-methylphenyl)sulfonylbenzamide
• 化学式: C₂₅H₂₃N₃O₆S
• 分子量: 493.54
• InChiKey: VBOMQUMVXOOHIB-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.5
• 重原子数：
  35
• 可旋转键数：
  6
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.16
• 拓扑面积：
  132
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  N1-{3-methoxy-4-(N-methyl-5-nitro-1H-3-indolyl)methylbenzoyl}-2-methyl-1-benzenesulfonamide 在 氢气 作用下， 以 四氢呋喃 为溶剂， 反应 2.0h， 以88%的产率得到4-[(5-氨基-1-甲基-1H-吲哚-3-基)甲基]-3-甲氧基-N-[(2-甲基苯基)磺酰基]苯甲酰胺
  参考文献：
  名称：

  通往扎鲁司特的新颖高效途径

  摘要：

  扎鲁司特是一种治疗哮喘等过敏性肺部疾病的重要药物，采用五步法合成，产量高，成本低。

  DOI：

  10.1021/op049869i
• 作为产物：
  描述：

  3-戊烯-2-酮,3,4-二氟-,(3Z)-(9CI) 在 盐酸 、 氯化亚砜 作用下， 以 四氢呋喃 、 二氯甲烷 、 水 、 N,N-二甲基甲酰胺 为溶剂， 反应 3.33h， 生成 N1-{3-methoxy-4-(N-methyl-5-nitro-1H-3-indolyl)methylbenzoyl}-2-methyl-1-benzenesulfonamide
  参考文献：
  名称：

  Investigation into the Acidification Process of Zafirluskast Nitroacid Leads to a Surprising Improvement in Product Quality

  摘要：

  An investigation into the acidification step of the zafirlukast nitroacid process was conducted by varying a range of parameters, including acid molarity, addition time, final pH, and temperature. A significant and unexpected improvement in product quality was achieved by using dilute rather than concentrated acid, independent of the final pH, and without a reduction in yield. The change to the dilute-acid process could be accommodated within the constraints of the existing registered process.

  DOI：

  10.1021/op049911+

文献信息

• [EN] PROCESS FOR THE PREPARATION OF ZAFIRLUKAST AND ANALOGS THEREOF<br/>[FR] PROCÉDÉ DE PRÉPARATION DU ZAFIRLUKAST ET DE SES ANALOGUES
  申请人：COUNCIL SCIENT IND RES

  公开号：WO2019130334A1

  公开（公告）日：2019-07-04

  The present invention relates to a process for the preparation of (1-alkylindol-3-ylmethyl) benzoic acid derivatives, in particular Zafirlukast and analogs thereof. Further, this process is based on protection group free and C-H bond activation strategy involving all step catalytic transformation sequence and comprises the following steps: Sonogashira coupling, indole formation by Sp3 C-H activation, reductive hydrogenation and amidation.

  本发明涉及一种制备(1-烷基吲哚-3-基甲基)苯甲酸衍生物的方法，特别是扎非鲁卡斯特及其类似物的制备方法。此外，该方法基于无保护基和C-H键活化策略，涉及所有步骤的催化转化序列，包括以下步骤：Sonogashira偶联、通过Sp3 C-H活化形成吲哚、还原氢化和酰胺化。
• Org. Process Res. Dev. 2004, 8, 952-954
  作者：

  DOI：——

  日期：——
• Investigation into the Acidification Process of Zafirluskast Nitroacid Leads to a Surprising Improvement in Product Quality
  作者：Claire L. Ancell、Ian Derrick、Jonathan D. Moseley、Jeffery A. Stott

  DOI：10.1021/op049911+

  日期：2004.9.1

  An investigation into the acidification step of the zafirlukast nitroacid process was conducted by varying a range of parameters, including acid molarity, addition time, final pH, and temperature. A significant and unexpected improvement in product quality was achieved by using dilute rather than concentrated acid, independent of the final pH, and without a reduction in yield. The change to the dilute-acid process could be accommodated within the constraints of the existing registered process.
• A Novel and Efficient Route to Zafirlukast
  作者：Keesari Srinivas、Neti Srinivasan、Muddasani Rama Krishna、Chinta Raveendra Reddy、Muthulingam Arunagiri、Routhu Lalitha、Kikkuru Sri Rami Reddy、Bijjula Sreenivasa Reddy、Ghanta Mahesh Reddy、Padi Pratap Reddy、Muppa Kishore Kumar、Manne Satyanaraya Reddy

  DOI：10.1021/op049869i

  日期：2004.11.1

  Zafirlukast, an important drug for allergic pulmonary disorders such as asthma, is synthesized by a five-step, high-yielding, and inexpensive process.

  扎鲁司特是一种治疗哮喘等过敏性肺部疾病的重要药物，采用五步法合成，产量高，成本低。