氫桂皮醯胺 | 17193-30-5

• 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
• 中文名称: 氫桂皮醯胺
• 中文别名: 3-苯丙醯胺
• 英文名称: (S)-(+)-α-methylamino-β-phenylpropionamide
• 英文别名: N-methyl phenylalaninamide；N-Me-Phe-NH2；N-methyl-L-phenylalaninamide；H-(N-Me)Phe-NH2；Nalpha-Methyl-L-phenylalaninamide；(2S)-2-(methylamino)-3-phenylpropanamide
• CAS: 17193-30-5
• 化学式: C₁₀H₁₄N₂O
• 分子量: 178.234
• InChiKey: PYRTVXRJEYPGJX-VIFPVBQESA-N

物化性质

• 沸点：
  353.3±35.0 °C(Predicted)
• 密度：
  1.078±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.1
• 重原子数：
  13
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.3
• 拓扑面积：
  55.1
• 氢给体数：
  2
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  氫桂皮醯胺 在 5% Pd on active carbon N-甲基吗啉 、 氢气 、 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 甲醇 、 N,N-二甲基甲酰胺 为溶剂， 25.0 ℃ 、101.33 kPa 条件下， 生成 4-Amino-N-((S)-1-carbamoyl-2-phenyl-ethyl)-N-methyl-butyramide
  参考文献：
  名称：

  新型Asp32替代四肽类似物作为有效和选择性的CCK-A激动剂。

  摘要：

  一系列通式为Boc-Trp-Lys（Tac）-N（R）-（CH2）nCON（R'）Phe-NH2的新颖CCK四肽类似物（Tac =邻甲苯基氨基羰基），其中R，R'= H或Me且n = 1-5，已经合成和测试。这些类似物在倒数第二个位置缺少酸性残基，显示出令人惊讶的高CCK-A受体亲和力和选择性。N-甲基化模式对CCK-A受体亲和力的影响显示出对n = 1、2或3的类似物的一致趋势，其中二-N-甲基化类似物在每种情况下均具有最高亲和力。然而，通过最大PI水解百分数测量，这些类似物均不具有完全的激动剂活性。两种受构象限制的类似物也显示出高CCK-A受体亲和力和选择性，以及几乎最大的激动剂活性。此外，

  DOI：

  10.1021/jm00037a005
• 作为产物：
  描述：

  N-(9-芴甲氧羰酰基)-N-甲基-L-苯丙氨酸 在 氯甲酸乙酯 、 三乙胺 、 ammonium hydroxide 、 哌啶 作用下， 以 四氢呋喃 、 N,N-二甲基甲酰胺 为溶剂， 反应 25.0h， 以286 g的产率得到氫桂皮醯胺
  参考文献：
  名称：

  Chemical Models of Peptide Formation in Translation

  摘要：

  Ribosomal incorporations of N-alkyl amino acids including proline are slower than incorporations of non-N-alkyl L-amino acids. The chemical reactivity hypothesis proposes that these results and the exclusion of nonproline N-alkyl amino acids from the genetic code are explained by intrinsic chemical reactivities of the amino and nucleophiles. However, there is little data on the reactivities relevant to physiological conditions. Here, we use nonenzymatic, aqueous-based, buffered reactions with formylmethionine-N-hydroxysuccinimide ester to model II amino acid nucleophiles in dipeptide formation. The relative rates in the nonenzymatic and translation systems correlate well. supporting the chemical reactivity hypothesis and arguing that peptide bond formation, not accommodation, is rate limiting, for natural Pro-tRNA(Pro) isoacceptors. The effects of N-substitution sterics, side chain sterics. Induction, and pK(a) were evaluated in the chemical model. The dominant factor affecting relative rates was found to he N-substitution sterics.

  DOI：

  10.1021/bi1000273

文献信息

• Synthesis of optically active α-methylamino acids and amides through biocatalytic kinetic resolution of amides
  作者：Mei-Xiang Wang、Jun Liu、De-Xian Wang、Qi-Yu Zheng

  DOI：10.1016/j.tetasy.2005.06.023

  日期：2005.7

  AJ270, a nitrile hydratase and amidase containing microbial whole-cell catalyst, under very mild conditions, a number of racemic α-methylamino amides were resolved into the corresponding optically active (S)-(+)-α-methylamino acids and (R)-(−)-α-methylamino amides. The steric requirement of the amidase against α-amino phenylacetamides bearing methyl group(s) at α-amino nitrogen and/or α-carbon was also

  由Rhodococcus sp。催化。AJ270，一种含有腈水合酶和酰胺酶的微生物全细胞催化剂，在非常温和的条件下，将许多外消旋的α-甲基氨基酰胺分解为相应的旋光性（S）-（+）-α-甲基氨基酸和（R） -（-）-α-甲基氨基酰胺。还研究了酰胺酶对α-氨基氮和/或α-碳上带有甲基的α-氨基苯基乙酰胺的空间需求。结合酰胺的化学水解，生物转化过程可以从容易获得的外消旋酰胺直接合成两种对映体形式的α-甲基氨基酸。
• Compounds for inhibiting &bgr;-amyloid peptide release and/or its synthesis
  申请人：Elan Pharmaceuticals, Inc.

  公开号：US06211235B1

  公开（公告）日：2001-04-03

  Disclosed are compounds which inhibit &bgr;-amyloid peptide release and/or its synthesis, and, accordingly, have utility in treating Alzheimer's disease. Also disclosed are pharmaceutical compositions comprising a compound which inhibits &bgr;-amyloid peptide release and/or its synthesis.

  揭示了一种抑制β-淀粉样肽释放和/或其合成的化合物，因此在治疗阿尔茨海默病方面具有用途。还揭示了包含抑制β-淀粉样肽释放和/或其合成的化合物的药物组合物。
• Polypeptides. Part VII. Variations of the phenylalanyl position in the C-terminal tetrapeptide amide sequence of the gastrins
  作者：H. Gregory、D. S. Jones、J. S. Morley

  DOI：10.1039/j39680000531

  日期：——

  The synthesis is described of analogues of L-tryptophyl-L-methionyl-L-aspartyl-L-phenylalanine amide (the C-terminal sequence of the gastrins) or its N-benzyloxycarbonyl, -t-butoxycarbonyl, or -carbamoyl derivatives wherein the phenylalanyl residue has undergone replacement by other naturally occuring amino-acyl residues or by αα-disubstituted amino-acyl residues, or has been modified by (a) substitution

  描述了L-色氨酸-L-甲硫酰基-L-天冬氨酰-L-苯丙氨酸酰胺（胃泌素的C-末端序列）或其N-苄氧羰基，-叔丁氧羰基或-氨基甲酰基衍生物的类似物的合成。苯丙氨酰基残基已被其他天然存在的氨基酰基残基或αα-二取代的氨基酰基残基取代，或已通过（a）在对位取代芳环进行修饰，（b）芳环的氢化，（c）亚氨基从α-碳原子转换为β-碳原子，（d）将苯环从β-碳原子转换为α-碳原子，（e）取代β-碳原子上的羟基，或（f）亚氨基的甲基化。
• Methods and compounds for inhibiting &bgr;-amyloid peptide release and/or its synthesis
  申请人：Elan Pharmaceuticals, Inc.

  公开号：US06191166B1

  公开（公告）日：2001-02-20

  Disclosed are compounds which inhibit &bgr;-amyloid peptide release and/or its synthesis, and, accordingly, have utility in treating Alzheimer's disease. Also disclosed pharmaceutical compositions comprising a compound which inhibits &bgr;-amyloid peptide release and/or its synthesis as well as methods for treating Alzheimer's disease both prophylactically and therapeutically with such pharmaceutical compositions.

  揭示了一种抑制β-淀粉样肽释放和/或合成的化合物，因此在治疗阿尔茨海默病方面具有用途。还揭示了包括抑制β-淀粉样肽释放和/或合成的化合物的药物组合物，以及使用这种药物组合物预防性和治疗性地治疗阿尔茨海默病的方法。
• 2-Substituted Penems with Amino Acid-Related Side Chains: Synthesis and Antibacterial Activity of a New Series of .beta.-Lactam Antibiotics
  作者：Maria Altamura、Enzo Perrotta、Piero Sbraci、Vittorio Pestellini、Federico Arcamone、Giuseppe Cascio、Laura Lorenzi、Giuseppe Satta、Grazia Morandotti、Roberta Sperning

  DOI：10.1021/jm00021a013

  日期：1995.10

  A new series of 6-(hydroxyethyl)penems 2-substituted with amino acid-related side chains was synthesized. The nature of the amino acyl derivative proved to be crucial both from a synthetic point of view, as beta-lactam ring opening can compete with C-2 nucleophilic substitution, and for antibacterial activity. Primary amino acid amides emerged as the most suitable side chains for enhancing permeability

  合成了一系列新的6-（羟乙基）青霉烯2-氨基酸相关的侧链取代。从合成的观点来看，氨基酰基衍生物的性质被证明是至关重要的，因为β-内酰胺开环可以与C-2亲核取代竞争，并且具有抗菌活性。伯氨基酸酰胺作为增强通过革兰氏阴性外膜渗透性的最合适的侧链出现。新的2-[（（氨基酰胺基）甲基]青霉烯3a-u）的体外活性受酰胺部分的性质和位置，环状酰胺的环大小以及氨基酸构型的影响。