(S)-2-((S)-2-(tert-butoxycarbonylamino)-3-phenylpropanamido)-3-phenylpropyl acetate

• 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: (S)-2-((S)-2-(tert-butoxycarbonylamino)-3-phenylpropanamido)-3-phenylpropyl acetate
• 英文别名: [(2S)-2-[[(2S)-2-[(2-methylpropan-2-yl)oxycarbonylamino]-3-phenylpropanoyl]amino]-3-phenylpropyl] acetate
• 化学式: C₂₅H₃₂N₂O₅
• 分子量: 440.539
• InChiKey: DDNABHAQYYBVSZ-VXKWHMMOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.2
• 重原子数：
  32
• 可旋转键数：
  12
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  93.7
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  (S)-2-((S)-2-(tert-butoxycarbonylamino)-3-phenylpropanamido)-3-phenylpropyl acetate 在 lithium aluminium tetrahydride 、 三乙胺 、 三氟乙酸 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 2.0h， 生成 橙黄胡椒酰胺
  参考文献：
  名称：

  金色酰胺醇酯及其氟化衍生物及制备方法和应用

  摘要：

  本发明属于医药技术领域，公开了金色酰胺醇酯及其氟化衍生物及制备方法和应用。通式如下所示的金色酰胺醇酯、金色酰胺醇酯氟化衍生物或金色酰胺醇酯及其氟化衍生物药学上可接受的盐：其中，R1表示OH、CH2OH或OCOCH3；R2、R3和R4分別独立表示H、烷基或F。该金色酰胺醇酯及其氟化衍生物或药学上可接受的盐对预防或治疗流感病毒，特别是甲型流感病毒引起的感染具有很好的效果。对金色酰胺醇酯进行氟化改造使金色酰胺醇酯的生物活性更强。该金色酰胺醇酯及其氟化衍生物作用靶标既针对病毒，也针对宿主细胞，故不易产生耐药。

  公开号：

  CN112500308A
• 作为产物：
  描述：

  BOC-L-苯丙氨酸琥珀酰亚胺酯 在 吡啶 、 三乙胺 作用下， 以 四氢呋喃 为溶剂， 生成 (S)-2-((S)-2-(tert-butoxycarbonylamino)-3-phenylpropanamido)-3-phenylpropyl acetate
  参考文献：
  名称：

  A dipeptide derivative fromHypericum japonicum

  摘要：

  The structure of a novel peptide analogue saropeptate, N-benzoyl-L-phenylalanyl-L-phenylalaninol acetate, isolated from the whole plant of H. japonicum was elucidated by spectroscopic analysis and its absolute configuration determined by comparison with four synthetic diastereoisomers.

  DOI：

  10.1016/0031-9422(91)80083-d

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.