(S)-2-((S)-2-(((9H-fluoren-9-yl)methoxy)carbonylamino)-3-(1-trityl-1H-imidazol-4-yl)propanamido)-3-phenylpropyl acetate | 1349999-03-6

• 分子结构分类: 有机化合物 - 苯类化合物 - 三苯基化合物
• 英文名称: (S)-2-((S)-2-(((9H-fluoren-9-yl)methoxy)carbonylamino)-3-(1-trityl-1H-imidazol-4-yl)propanamido)-3-phenylpropyl acetate
• 英文别名: [(2S)-2-[[(2S)-2-(9H-fluoren-9-ylmethoxycarbonylamino)-3-(1-tritylimidazol-4-yl)propanoyl]amino]-3-phenylpropyl] acetate
• CAS: 1349999-03-6
• 化学式: C₅₁H₄₆N₄O₅
• 分子量: 794.95
• InChiKey: BUHFSLURJCBLKC-OKAUKWFNSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  9.2
• 重原子数：
  60
• 可旋转键数：
  17
• 环数：
  8.0
• sp3杂化的碳原子比例：
  0.18
• 拓扑面积：
  112
• 氢给体数：
  2
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  N-Boc-L-苯丙氨醇 在 N-甲基吗啉 、 吡啶 、 盐酸 、 1-羟基苯并三唑 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 作用下， 以 1,4-二氧六环 、 N,N-二甲基甲酰胺 为溶剂， 反应 2.67h， 生成 (S)-2-((S)-2-(((9H-fluoren-9-yl)methoxy)carbonylamino)-3-(1-trityl-1H-imidazol-4-yl)propanamido)-3-phenylpropyl acetate
  参考文献：
  名称：

  Structure-Based Rationale Design and Synthesis of Aurantiamide Acetate Analogues - Towards a New Class of Potent Analgesic and Anti-inflammatory Agents

  摘要：

  A series of new aurantiamide acetate analogues were synthesized by modifying its N‐terminal substitution and the amino acid residue. The structure of all these compounds was established on the basis of analytical and spectral studies. All the new derivatives were evaluated in vivo for their analgesic activity by tail flick method in mice and anti‐inflammatory activity against carrageenan‐induced oedema in albino rats at different doses (25, 50 and 100 mg/kg body weight). All the compounds exhibited significant pharmacological activity with no ulcerogenic liability. In particular, pentapeptides and tricosamers (30 amino acids) containing analogues have demonstrated high potency than the reference standards. These compounds hold promise for further development.

  DOI：

  10.1111/j.1747-0285.2012.01331.x

文献信息

• Design and synthesis of new N-(fluorenyl-9-methoxycarbonyl) (Fmoc)-dipeptides as anti-inflammatory agents
  作者：Chiao-Ting Yen、Tsong-Long Hwang、Yang-Chang Wu、Pei-Wen Hsieh

  DOI：10.1016/j.ejmech.2008.11.008

  日期：2009.5

  Twenty-four new dipeptide analogs (1-24) of aurantiamide acetate were designed, synthesized, and assayed for effects on superoxide anion generation and elastase release by human neutrophils in response to fMLP/CB. Among them, seven N-(fluorenyl-9-methoxycarbonyl) (Fmoc)-dipeptides (6, 9,12, 14, 17, 18 and 20) showed potent inhibitory effects. Compounds 9 and 18 showed the most selective effects against human neutrophil elastase release, with IC50 values of 0.8+/-0.1 and 1.7+/-0.6 mu M, respectively, and were 130-fold more potent than phenylmethylsulfonyl fluoride (PMSF), the positive control, in this anti-inflammatory assay. These two compounds could be developed as new lead antiinflammatory agents. (C) 2008 Elsevier Masson SAS. All rights reserved.
• Structure-Based Rationale Design and Synthesis of Aurantiamide Acetate Analogues - Towards a New Class of Potent Analgesic and Anti-inflammatory Agents
  作者：Ramesh Suhas、Dase Channe Gowda

  DOI：10.1111/j.1747-0285.2012.01331.x

  日期：2012.5

  A series of new aurantiamide acetate analogues were synthesized by modifying its N‐terminal substitution and the amino acid residue. The structure of all these compounds was established on the basis of analytical and spectral studies. All the new derivatives were evaluated in vivo for their analgesic activity by tail flick method in mice and anti‐inflammatory activity against carrageenan‐induced oedema in albino rats at different doses (25, 50 and 100 mg/kg body weight). All the compounds exhibited significant pharmacological activity with no ulcerogenic liability. In particular, pentapeptides and tricosamers (30 amino acids) containing analogues have demonstrated high potency than the reference standards. These compounds hold promise for further development.