ethyl 2-<(cyclohexylmethyl)amino>acetate | 144006-28-0

• 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: ethyl 2-<(cyclohexylmethyl)amino>acetate
• 英文别名: Ncha-OEt；ethyl (cyclohexylmethyl)glycinate；Ethyl 2-[(cyclohexylmethyl)amino]acetate；ethyl 2-(cyclohexylmethylamino)acetate
• CAS: 144006-28-0
• 化学式: C₁₁H₂₁NO₂
• mdl: MFCD12166154
• 分子量: 199.293
• InChiKey: ORQZMFSPZSOCNN-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  14
• 可旋转键数：
  6
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.909
• 拓扑面积：
  38.3
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  ethyl 2-<(cyclohexylmethyl)amino>acetate 在 sodium hydroxide 作用下， 以 四氢呋喃 、 甲醇 为溶剂， 反应 2.0h， 生成 1,1-dimethylethyl N-(carboxymethyl)-N-(cyclohexylmethyl)carbamate
  参考文献：
  名称：

  Stereoselective synthesis of renin inhibitor BILA 2157 BS

  摘要：

  我们已经开发出一种具有收敛性和立体选择性的口服活性肾素抑制剂BILA 2157 BS的合成方法。使用了三种构建模块来生成抑制剂的基本骨架。关键特征是从乙烯溴化物前体中晚期修饰2-氨基-4-噻唑基杂环。这种合成序列总共需要22个化学步骤，提供了0.6公斤的BILA 2157 BS，总产率为7.3%。关键词：肾素、抑制剂、肽类模拟物、立体选择性合成。

  DOI：

  10.1139/v99-233
• 作为产物：
  描述：

  甘氨酸乙酯盐酸盐 、 环己烷基甲醛 在 sodium cyanoborohydride 作用下， 以 乙醇 为溶剂， 反应 72.0h， 生成 ethyl 2-<(cyclohexylmethyl)amino>acetate
  参考文献：
  名称：

  血管紧张素转化酶抑制剂：N-取代的单环和双环氨基酸衍生物。

  摘要：

  N-（3-巯基丙酰基）-N-芳基甘氨酸（14a-x），-N-芳基丙氨酸（15a，b），-N-环烷基甘氨酸（16a-k）和-1,2,3,4-的合成描述了四氢异喹啉-3-羧酸（17a-d），-1,2,3,4-四氢喹啉-2-羧酸（18a-f）和-二氢吲哚-2-羧酸（19a-k）。报道了每种化合物对血管紧张素转化酶（ACE）的体外抑制作用，并讨论了每个系列的结构-活性关系。讨论了ACE的体内抑制作用和各系列代表性化合物的降压作用。最有效的化合物19d的体外ACE IC50为2.6 X 10（-9）M，并且以10 mg / kg po的剂量在85 mm的自发性高血压大鼠中降低了血压。

  DOI：

  10.1021/jm00363a011

文献信息

• Selective Functionalization of Aliphatic Amines via Myoglobin-Catalyzed Carbene N–H Insertion
  作者：Viktoria Steck、Gopeekrishnan Sreenilayam、Rudi Fasan

  DOI：10.1055/s-0039-1690007

  日期：2020.2

  for their ability to catalyze a variety of abiological carbene transfer reactions including the functionalization of amines via carbene insertion into N-H bonds. However, the scope of myoglobin and other hemoprotein-based biocatalysts in the context of this transformation has been largely limited to aniline derivatives as the amine substrates and ethyl diazoacetate as the carbene donor reagent. In this

  工程化肌红蛋白最近因其催化各种非生物卡宾转移反应的能力而受到关注，包括通过卡宾插入 NH 键来官能化胺。然而，在这种转化的背景下，肌红蛋白和其他基于血红素蛋白的生物催化剂的范围很大程度上限于作为胺底物的苯胺衍生物和作为卡宾供体试剂的重氮乙酸乙酯。在本报告中，我们描述了一种基于工程肌红蛋白的催化剂的开发，该催化剂可用于促进各种取代苄胺和 α-重氮乙酸酯的卡宾 NH 插入反应，具有高效率（82-99% 转化率）、更高的催化转化率（高达至 7,000），并且对所需的单插入产物具有出色的化学选择性（高达 99%）。这种转化的范围可以扩展到环状脂肪胺。这些研究扩展了可用于选择性形成 CN 键的生物催化工具箱，CN 键在许多天然和合成的生物活性化合物中普遍存在。
• [EN] INDOLE- 3 -GLYOXYLAMIDE DERIVATIVES FOR USE AS CALCIUM ION CHANNEL MODULATORS<br/>[FR] DÉRIVÉS D'INDOLE-3-GLYOXYLAMIDE DESTINÉS À ÊTRE UTILISÉS COMME MODULATEURS DES CANAUX CALCIQUES
  申请人：LECTUS THERAPEUTICS LTD

  公开号：WO2009133387A1

  公开（公告）日：2009-11-05

  Compounds of formula (I) are of use in treating a range of conditions, including pain.

  化合物的化学式（I）可用于治疗一系列疾病，包括疼痛。
• [EN] CALCIUM ION CHANNEL MODULATORS & USES THEREOF<br/>[FR] MODULATEURS DES CANAUX IONIQUES CALCIQUES ET LEURS UTILISATIONS
  申请人：LECTUS THERAPEUTICS LTD

  公开号：WO2010035032A1

  公开（公告）日：2010-04-01

  Compounds of formula (I), wherein R1 is hydrogen, hydroxyl or aralkyl; R2 is an optionally substituted alkyl, aryl or heteroaryl (said substituents are selected from hydroxyl, alkoxyl, haloalkoxyl, aryl, heteroaryl, cycloalkyl, amino, monoalkylamino, dialkylamino, alkylsulphonyl, alkylsulphinyl, alkylsulphonylamino, acylamino, saturated or partially unsaturated heterocyclic groups and groups of formula COY); W is selected from oxygen, sulphur, groups of formula NR7, wherein R7 is hydrogen, alkyl, aryl or heteroaryl and groups of formula CR8R9, wherein R8 and R9 are hydrogen, alkyl, aryl or heteroaryl; and X is selected from nitrogen and groups of formula CR10, wherein R10 is hydrogen, alkyl, aryl, heteroaryl, halogen or haloalkyl, inhibit the interaction between Cavx channels and Cavβ proteins and are of use in the treatment and prevention of a number of diseases and conditions including pain and lower urinary tract disorders.

  式(I)中的化合物，其中R1是氢、羟基或芳基烷基；R2是可选择取代的烷基、芳基或杂环芳基（所述取代基选自羟基、烷氧基、卤代烷氧基、芳基、杂环芳基、环烷基、氨基、单烷基氨基、双烷基氨基、烷基磺酰基、烷基亚砜基、烷基磺酰氨基、酰氨基、饱和或部分不饱和的杂环族和式COY）；W选自氧、硫、式NR7的基团，其中R7是氢、烷基、芳基或杂环芳基，以及式CR8R9的基团，其中R8和R9是氢、烷基、芳基或杂环芳基；X选自氮和式CR10的基团，其中R10是氢、烷基、芳基、杂环芳基、卤素或卤代烷基，能够抑制Cavx通道与Cavβ蛋白之间的相互作用，并可用于治疗和预防包括疼痛和下尿路障碍在内的多种疾病和症状。
• Retroviral protease inhibitors derived from 3-chloro-2-chloromethyl-1-propene
  申请人：AMERICAN CYANAMID COMPANY

  公开号：EP0492136A2

  公开（公告）日：1992-07-01

  The invention provides compounds of the formula: wherein Q, X, Y, Z, R₁, R₂ and R₃ are defined in the specifications useful as inhibitors of HIV protease enzyme.

  本发明提供了式中化合物： 其中 Q、X、Y、Z、R₁、R₂ 和 R₃ 在说明书中定义，可用作 HIV 蛋白酶的抑制剂。
• Further Studies on Nociceptin-Related Peptides:  Discovery of a New Chemical Template with Antagonist Activity on the Nociceptin Receptor
  作者：Remo Guerrini、Girolamo Calo'、Raffaella Bigoni、Anna Rizzi、Katia Varani、Geza Toth、Stefania Gessi、Eiji Hashiba、Yoshio Hashimoto、David G. Lambert、Pier Andrea Borea、Roberto Tomatis、Severo Salvadori、Domenico Regoli

  DOI：10.1021/jm990075h

  日期：2000.7.1

  Three series of nociceptin (NC)-related peptides were synthesized and their abilities (i) to bind to the NC sites expressed in mouse forebrain membranes, (ii) to inhibit the electrically evoked contraction of the mouse vas deferens, and (iii) to inhibit forskolin-stimulated cAMP accumulation in Chinese hamster ovary cells expressing the human recombinant NC receptor (CHONCR) were investigated. The compounds of the first series (a series) have an ordinary Xaa(1)-Gly(2) bond, those of the second series (b series) have a Xaa(1)Psi(CH2-NH)Gly(2) pseudopeptide bond, and those of the third series (c series) have a peptoid (Nxaa(1)-Gly(2)) structure. The affinity values measured in the binding assay and in the two functional assays with the compounds of the three series showed high levels of correlation. Thus, (I) the compounds of the a series in which Phe(1) was substituted with Tyr, Cha, or Leu acted as potent NC receptor agonists; (II) the b series compounds behaved as NC receptor antagonists in the mouse vas deferens and as full agonists in CHONCR cells with different potencies depending on the first amino acid residue, [Phe(1)Psi(CH2-NH)Gly(2)]NC(1-17)NH2 and [Phe(1)Psi(CH2-NH)Gly(2)]NC(1-13)NH2 being the most potent compounds; (III) the compounds of the third series were all inactive both as agonists and as antagonists with the exception of [Nphe(1)]NC(1-17)NH2 and [Nphe(1)]NC(1-13)NH2, which behaved as NC receptor antagonists both in the isolated tissue and in CHONCR cells (pK(B) 6.1-6.4). In conclusion, this study demonstrates that chemical requirements for NC receptor agonists are different from those of antagonists. Moreover, modifications of the steric orientation of the aromatic residue Phe(1) in the NC sequence as obtained with the pseudopeptide bond between Phe(1) and Gly(2) or with the displacement of the benzyl side chain by one atom, as in Nphe(1), lead respectively to reduction or elimination of efficacy. Indeed, in contrast to [Phe(1)Psi(CH2-NH)Gly(2)]NC(1-13)NH2 which has been reported to exhibit agonist activity in several assays involving either central or recombinant NC receptors, [Nphe(1)]NC(1-13)NH2 antagonizes the effect of NC at human recombinant NC receptors and in the mouse tail withdrawal assay.