methyl (2-(1-methyl-5-(4-methylbenzoyl)-1H-pyrrol-2-yl) acetyl) glycinate | 93962-13-1

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: methyl (2-(1-methyl-5-(4-methylbenzoyl)-1H-pyrrol-2-yl) acetyl) glycinate
• 英文别名: Methyl 2-[[2-[1-methyl-5-(4-methylbenzoyl)pyrrol-2-yl]acetyl]amino]acetate
• CAS: 93962-13-1
• 化学式: C₁₈H₂₀N₂O₄
• 分子量: 328.368
• InChiKey: ZZVSEQRZMCYSEB-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  24
• 可旋转键数：
  7
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.28
• 拓扑面积：
  77.4
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  methyl (2-(1-methyl-5-(4-methylbenzoyl)-1H-pyrrol-2-yl) acetyl) glycinate 在 potassium carbonate 、 1-羟基苯并三唑 、 N,N'-二环己基碳二亚胺 、 sodium hydroxide 作用下， 以 二氯甲烷 、 水 为溶剂， 反应 3.0h， 生成 哌氨托美丁
  参考文献：
  名称：

  Synthesis and Process Optimization of Amtolmetin: An Antiinflammatory Agent

  摘要：

  Efforts toward the synthesis and process optimization of amtolmetin guacil 1 are described. High-yielding electrophilic substitution followed by Wolf-Kishner reduction are the key features in the novel synthesis of tolmetin 2 which is an advanced intermediate of 1.

  DOI：

  10.1021/op900284w
• 作为产物：
  描述：

  托美丁甲酯 在 三乙胺 、 sodium hydroxide 作用下， 以 甲醇 、 二氯甲烷 、 水 为溶剂， 反应 2.83h， 生成 methyl (2-(1-methyl-5-(4-methylbenzoyl)-1H-pyrrol-2-yl) acetyl) glycinate
  参考文献：
  名称：

  Synthesis and Process Optimization of Amtolmetin: An Antiinflammatory Agent

  摘要：

  Efforts toward the synthesis and process optimization of amtolmetin guacil 1 are described. High-yielding electrophilic substitution followed by Wolf-Kishner reduction are the key features in the novel synthesis of tolmetin 2 which is an advanced intermediate of 1.

  DOI：

  10.1021/op900284w

文献信息

• Pyrrole-2-acetylamino acid derivatives
  申请人：McNeilab, Inc.

  公开号：EP0115424A1

  公开（公告）日：1984-08-08

  Novel pyrrole-2-acetylamino compounds of the formula (5): and salts thereof, wherein R" is H, C,-6 alkyl, (CH2)nCO2H, CH2CH2SCH3, (CH2)4NH2 or (CH2)2CONH2; and n is 1 or 2; and Y is hydrogen and Q is CH3 or Y is CH3 and Q is Cl, have utility as anti-inflammatory agents and esters of the compounds of the above formula which are useful as intermediates to make said compounds. When Y is H and Q is CH3, the compounds have, in lower dosages, the same nonsteroidal anti- inflammatory utility as tolmetin and when Y is CH3 and Q is Cl, the compounds have the same analgesic and anti- inflammatory utility as zomepirac but with reduced liability toward gastrointestinal irritation.

  式 (5) 的新型吡咯-2-乙酰氨基化合物： 及其盐类，其中 R "为 H、C,-6 烷基、(CH2)nCO2H、CH2CH2SCH3、(CH2)4NH2 或 (CH2)2CONH2；n 为 1 或 2；Y 为氢，Q 为 CH3 或 Y 为 CH3，Q 为 Cl，可用作抗炎剂，上式化合物的酯类可用作制造上述化合物的中间体。当 Y 为 H、Q 为 CH3 时，这些化合物在较低剂量下具有与托美汀相同的非甾体抗炎作用；当 Y 为 CH3、Q 为 Cl 时，这些化合物具有与佐美吡拉克相同的镇痛和抗炎作用，但胃肠道刺激性降低。
• Synthesis and Process Optimization of Amtolmetin: An Antiinflammatory Agent
  作者：Lekkala Amarnath Reddy、Saurya Chakraborty、Rodda Swapna、Dinesh Bhalerao、Golla China Malakondaiah、Mylavarapu Ravikumar、Abhijeet Kumar、Gade Srinivas Reddy、Jyothirmayi Naram、Namrata Dwivedi、Arnab Roy、Vurimidi Himabindu、Bangaru Babu、Apurba Bhattacharya、Rakeshwar Bandichhor

  DOI：10.1021/op900284w

  日期：2010.3.19

  Efforts toward the synthesis and process optimization of amtolmetin guacil 1 are described. High-yielding electrophilic substitution followed by Wolf-Kishner reduction are the key features in the novel synthesis of tolmetin 2 which is an advanced intermediate of 1.