(E)-4-amino-5-phenyl-pent-2-enoic acid ethyl ester | 244033-75-8

• 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: (E)-4-amino-5-phenyl-pent-2-enoic acid ethyl ester
• 英文别名: Ethyl (2E)-4-amino-5-phenyl-2-pentenoate；ethyl (E,4S)-4-amino-5-phenylpent-2-enoate
• CAS: 244033-75-8
• 化学式: C₁₃H₁₇NO₂
• 分子量: 219.283
• InChiKey: OSOJJKZDZDPLSA-IDVQTMNDSA-N

物化性质

• 沸点：
  348.5±42.0 °C(Predicted)
• 密度：
  1.064±0.06 g/cm3(Temp: 20 °C; Press: 760 Torr)(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.8
• 重原子数：
  16
• 可旋转键数：
  6
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.31
• 拓扑面积：
  52.3
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (E)-4-amino-5-phenyl-pent-2-enoic acid ethyl ester 在 4-二甲氨基吡啶 、 水 、 三乙酰氧基硼氢化钠 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 、 三乙胺 、 三氟乙酸 、 lithium hydroxide 作用下， 以 四氢呋喃 、 甲醇 、 二氯甲烷 为溶剂， 反应 92.0h， 生成 (E)-[4-(1-benzyl-3-methylcarbamoylallylcarbamoyl)-4-isopropylaminobutylamino]acetic acid benzyl ester
  参考文献：
  名称：

  Anti-malarial activity of new N-acetyl-l-leucyl-l-leucyl-l-norleucinal (ALLN) derivatives against Plasmodium falciparum

  摘要：

  Malaria is the most common of the parasitic diseases in tropical and subtropical regions. Adverse side effects of anti-malarial drugs have precluded them as a potential clinical drug. In this study, novel derivatives of N-acetyl-L-leucyl-L-leucyl-L-norleucinal (ALLN) based on a variety of dipeptidyl alpha,beta-unsaturated amides containing lysine as a part were synthesized and evaluated. Lower toxicity was achieved by reducing or eliminating the tendency of forming chemically reactive and toxic intermediates and metabolites. The synthesized compounds were evaluated for anti-malarial efficacy against Plasmodium falciparum and cytotoxicity in human epitheloid carcinoma cervix (HeLa cells) by estimating the therapeutic index (TI). N-Methyl amide with N'-Boc protection among them exhibited strong anti-malarial activity and N-methyl amide with N'-m-methylbenzyl amide showed excellent anti-malarial activity with much lower toxicity than the ALLN. Therefore, the two chemicals, as well as the underlying design rationale, could be useful in the discovery and development of new anti-malarial drugs. (c) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2012.12.100
• 作为产物：
  描述：

  BOC-PHE-甲氧基甲胺 在 lithium aluminium tetrahydride 、 potassium tert-butylate 、 三氟乙酸 作用下， 以 四氢呋喃 为溶剂， 生成 (E)-4-amino-5-phenyl-pent-2-enoic acid ethyl ester
  参考文献：
  名称：

  Synthesis of densely functionalized pyrrolidinone templates by an intramolecular oxo-Diels–Alder reaction

  摘要：

  Preparation of densely functionalized pyrrolidinone templates, is a challenge for synthetic chemists. These templates are important building blocks for novel conformationally constrained natural products or for library generation of highly functionalized bi or polycyclic compounds. We discovered that trienes 6a-j undergo facile stereoselective intramolecular Diels-Alder reactions to generate densely functionalized cis fused pyrrolidinone templates 1a-j. These reactions allow for directed remote hydroxylation with complete control of stereochemistry. (C) 2002 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(02)01711-2

文献信息

• ALLN (N-acetyl-L-Leucyl-Lleucyl-L-norleucinal) 유도체 화합물을 유효성분으로 함유하는 말라리아 감염 질환의 예방 또는 치료용 조성물
  申请人：Wonkwang University Center for Industry-Academy Cooperation 원광대학교산학협력단(220040233365) BRN ▼403-82-09152

  公开号：KR101491624B1

  公开（公告）日：2015-02-10

  본 발명은 ALLN 유도체 화합물을 유효성분으로 함유하는 항 말라리아 조성물에 관한 것으로, 본 발명의 화합물들은 ALLN (N-acetyl-L-Leucyl-Lleucyl-L-norleucinal) 유도체 화합물을 유효성분으로 함유하는 말라리아 감염 질환의 예방 및 치료용 약학조성물로 사용할 수 있다.

  本发明涉及含有ALLN衍生物化合物作为有效成分的抗疟疾组合物，该化合物可用作预防和治疗疟疾感染疾病的药学组合物，其中该化合物包含ALLN（N-乙酰-L-亮氨酸-L-亮氨酸-L-正亮醛）衍生物化合物作为有效成分。
• Novel CADD-based peptidyl vinyl ester derivatives as potential proteasome inhibitors
  作者：Ke Mou、Bo Xu、Chao Ma、Xiaoming Yang、Xiaomin Zou、Yang Lü、Ping Xu

  DOI：10.1016/j.bmcl.2007.12.077

  日期：2008.3

  A series of peptidyl vinyl ester derivatives bearing three different P1 substitutions as potential proteasome inhibitors were studied. The target molecules were designed based on CADD (computer aided drug design) protocol and synthesized. Their activities toward proteasome and four human cancer cell lines (including hepatoma cell line (Bel-7402), myeloid leukemic cell line (HL-60), gastric cancer cell

  研究了一系列带有三个不同的P1取代基的肽基乙烯基酯衍生物，它们是潜在的蛋白酶体抑制剂。根据CADD（计算机辅助药物设计）协议设计目标分子并进行合成。它们对蛋白酶体和四种人类癌细胞系（包括肝癌细胞系（Bel-7402），髓样白血病细胞系（HL-60），胃癌细胞系（BGC-823）和鼻咽癌细胞系（KB））的活性为使用荧光测定法测试。两种化合物对蛋白酶体具有抑制活性，而四种化合物对HL-60和BGC-823的抗增殖活性较弱。
• α/γ4-Hybrid peptide helices: synthesis, crystal conformations and analogy with the α-helix
  作者：Anupam Bandyopadhyay、Sandip V. Jadhav、Hosahudya N. Gopi

  DOI：10.1039/c2cc32911e

  日期：——

  Synthesis, crystal conformations of α/γ4-hybrid peptide helices containing proteinogenic amino acid side-chains, and the analogy with the α-helix are reported. Results suggest that α/γ4-hybrid peptides adopted helical conformations with 12-membered H-bond pseudocycles in single crystals.

  报告了含有蛋白源氨基酸侧链的δ/δ³4-杂化肽螺旋的合成、晶体构象以及与δ-螺旋的类比。结果表明，δ/δ³4-杂交肽在单晶中具有 12 元 H 键假环的螺旋构象。
• Inhibition of the severe acute respiratory syndrome 3CL protease by peptidomimetic α,β-unsaturated esters
  作者：Jiun-Jie Shie、Jim-Min Fang、Tun-Hsun Kuo、Chih-Jung Kuo、Po-Huang Liang、Hung-Jyun Huang、Yin-Ta Wu、Jia-Tsrong Jan、Yih-Shyun E. Cheng、Chi-Huey Wong

  DOI：10.1016/j.bmc.2005.05.065

  日期：2005.9

  The proteolytic processing of polyproteins by the 3CL protease of severe acute respiratory syndrome coronavirus is essential for the viral propagation. A series of tripeptide alpha,beta-unsaturated esters and ketomethylene isosteres, including AG7088, are synthesized and assayed to target the 3CL protease. Though AG7088 is inactive (IC50 > 100 mu M), the ketomethylene isosteres and tripeptide alpha,beta-unsaturated esters containing both P1 and P2 phenylalanine residues show modest inhibitory activity (IC50 = 11-39 mu M). The Phe-Phe dipeptide inhibitors 18a-e are designed on the basis of computer modeling of the enzyme-inhibitor complex. The most potent inhibitor 18c with an inhibition constant of 0.52 mu M is obtained by condensation of the Phe-Phe dipeptide alpha,beta-unsaturated ester with 4-(dimethylamino)cinnamic acid. The cell-based assays also indicate that 18c is a nontoxic anti-SARS agent with an EC50 value of 0.18 mu M. (c) 2005 Elsevier Ltd. All rights reserved.
• Enantiomerically Pure α-Amino Aldehydes from Silylated α-Amino Acids
  作者：Buddy Soto-Cairoli、Jorge Justo de Pomar、John A. Soderquist

  DOI：10.1021/ol7028993

  日期：2008.1.1

  The disilylation of alpha-amino acids 1 to provide 2 (72-87%) was achieved without racemization. An unprecedented borane-mediated semi-reduction strategy was devised to convert 2 to stable, isolable oxazaborolidines 3 (100%) which were hydrolyzed to provide 5 (49-60%) as pure, stable compounds. Analysis of the Mosher amides (8) of the gamma-amino esters 7 reveals that <= 2% racemization occurs in the 1 -> 8 conversions.