methyl (2R)-6-amino-2-(phenylmethoxycarbonylamino)hexanoate | 188625-18-5

• 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
• 英文名称: methyl (2R)-6-amino-2-(phenylmethoxycarbonylamino)hexanoate
• CAS: 188625-18-5
• 化学式: C₁₅H₂₂N₂O₄
• 分子量: 294.351
• InChiKey: CZWJWNQZTSMVAZ-CYBMUJFWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.5
• 重原子数：
  21
• 可旋转键数：
  10
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.47
• 拓扑面积：
  90.6
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  methyl (2R)-6-amino-2-(phenylmethoxycarbonylamino)hexanoate 在 1-(3-二甲基氨基丙基)-3-乙基碳二亚胺 作用下， 以 二氯甲烷 为溶剂， 反应 7.0h， 生成 methyl (2R)-2-(benzyloxycarbonylamino)-6-(N-(phenylcarbonyloxy)formamido)hexanoate
  参考文献：
  名称：

  Syntheses of Amamistatin Fragments and Determination of Their HDAC and Antitumor Activity

  摘要：

  Amamistatins A and B are natural products found to have anti-proliferative effects against MCF-7, A549, and MKN45 human tumor cell lines (IC(50) 0.24-0.56 mu M). It was proposed that their activity was due to histone deacetylase (HDAC) inhibition mediated by the N-formyl-N-hydroxy lysine moiety. Amamistatin B fragment analogs were synthesized and screened for biological activity. These compounds were modest HDAC inhibitors and showed antitumor activity against MCF-7 and PC-3 human tumor cells.

  DOI：

  10.1021/ol070382e
• 作为产物：
  描述：

  甲醇 、 Cbz-D-赖氨酸 在 氯化亚砜 作用下， 反应 4.25h， 生成 methyl (2R)-6-amino-2-(phenylmethoxycarbonylamino)hexanoate
  参考文献：
  名称：

  Syntheses of Amamistatin Fragments and Determination of Their HDAC and Antitumor Activity

  摘要：

  Amamistatins A and B are natural products found to have anti-proliferative effects against MCF-7, A549, and MKN45 human tumor cell lines (IC(50) 0.24-0.56 mu M). It was proposed that their activity was due to histone deacetylase (HDAC) inhibition mediated by the N-formyl-N-hydroxy lysine moiety. Amamistatin B fragment analogs were synthesized and screened for biological activity. These compounds were modest HDAC inhibitors and showed antitumor activity against MCF-7 and PC-3 human tumor cells.

  DOI：

  10.1021/ol070382e

文献信息

• Oxidative Deamination of Various Primary Amines to the Corresponding Carbonyl Compounds by Using<i>N</i>-<i>tert</i>-Butylphenylsulfinimidoyl Chloride
  作者：Jun-ichi Matsuo、Asahi Kawana、Yoshio Fukuda、Teruaki Mukaiyama

  DOI：10.1246/cl.2001.712

  日期：2001.7

  Various linear and non-linear primary amines were oxidatively deaminated to afford the corresponding carbonyl compounds in good to excellent yields by the following procedure: (i) initial formation of their N-cyclohexylated or N-mesylated derivatives, (ii) subsequent oxidation of these derivatives by using N-tert-butylphenylsulfinimidoyl chloride (1) and DBU, (iii) one-pot acid-hydrolysis of thus formed

  通过以下程序将各种线性和非线性伯胺氧化脱氨基，以良好至极好的收率提供相应的羰基化合物：（i）它们的 N-环己基化或 N-甲磺酸化衍生物的初始形成，（ii）这些化合物的后续氧化通过使用 N-叔丁基苯基亚磺酰亚胺酰氯 (1) 和 DBU 制备衍生物，(iii) 将由此形成的亚胺一锅酸水解为羰基化合物。
• IBX/TBAB-Mediated Oxidation of Primary Amines to Nitriles
  作者：Géraldine Masson、Jieping Zhu、Fleur Drouet、Patrice Fontaine

  DOI：10.1055/s-0028-1087994

  日期：2009.4

  combination of o-iodoxybenzoic acid (IBX) and tetrabutylammonium bromide (TBAB) efficiently oxidizes primary amines to the corresponding nitriles in good to excellent yield under mild conditions. The reaction is racemization-free when applied to a chiral lysine derivative. o-iodoxybenzoic acid (IBX) - tetrabutylammonium bromide (TBAB) - amines - nitriles - oxidation - dehydrogenation

  邻碘氧苯甲酸（IBX）和四丁基溴化铵（TBAB）的组合可在温和的条件下将伯胺有效氧化成相应的腈，并具有良好的收率。当应用于手性赖氨酸衍生物时，该反应是无消旋的。 邻碘氧苯甲酸（IBX）-溴化四丁铵（TBAB）-胺-腈-氧化-脱氢
• Substituted chiral allosteric hemoglobin modifiers
  申请人：——

  公开号：US20030130523A1

  公开（公告）日：2003-07-10

  A family of substituted chiral allosteric effectors of hemoglobin is useful for delivering more oxygen to hypoxic and ischemic tissues by reducing the oxygen affinity of hemoglobin in whole blood.

  一种替代手性变构血红蛋白效应物家族，通过降低全血中血红蛋白的氧亲和力，有助于向低氧和缺血组织输送更多氧气。
• Solution-phase combinatorial synthesis via the olefin metathesis reaction
  作者：Dale L. Boger、Wenying Chai、Rachel S. Ozer、Carl-Magnus Andersson

  DOI：10.1016/s0960-894x(97)00043-7

  日期：1997.2

  The preparation of C-2-symmetric and unsymmetric chemical libraries by solution-phase techniques including the use of the olefin metathesis reaction to join and combinatorially randomize the length of a linking tether is detailed. (C) 1997, Elsevier Science Ltd.
• Amino acid, dipeptide and pseudodipeptide conjugates of ring-substituted 8-aminoquinolines: Synthesis and evaluation of anti-infective, β-haematin inhibition and cytotoxic activities
  作者：Kirandeep Kaur、Meenakshi Jain、Shabana I. Khan、Melissa R. Jacob、Babu L. Tekwani、Savita Singh、Prati Pal Singh、Rahul Jain

  DOI：10.1016/j.ejmech.2012.03.019

  日期：2012.6

  Three new series of 8-aminoquinolines with modifications in the side-chain by conjugation with amino acids, dipeptides and pseudodipeptides have been synthesized. The synthesized compounds were tested for in vitro antimalarial activity against chloroquine-sensitive and chloroquine-resistant Plasmodium falciparum strains, in vitro cytotoxicity in mammalian kidney cells (Vero), in vitro antileishmanial activity against Leishmania donovani, in vitro antimicrobial activity and in vitro inhibition of beta-haematin formation. The promising compounds were also evaluated for in vivo blood-schizontocidal antimalarial activity against Plasmodium berghei infected mice. The analogues 55 and 101 produced highest antimalarial activities, in vitro. Analogues 52 and 59 exhibited promising antileishmanial and broad spectrum of antifungal activities, respectively. (C) 2012 Elsevier Masson SAS. All rights reserved.