tert-butyl isoindolin-2-yl(methyl)carbamate | 78976-50-8

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 异吲哚及其衍生物
• 英文名称: tert-butyl isoindolin-2-yl(methyl)carbamate
• 英文别名: tert-butyl 1,3-dihydro-2H-isoindol-2-yl(methyl)carbamate；tert-butyl N-(1,3-dihydroisoindol-2-yl)-N-methylcarbamate
• CAS: 78976-50-8
• 化学式: C₁₄H₂₀N₂O₂
• 分子量: 248.325
• InChiKey: QBPBDGSGYSAGKJ-UHFFFAOYSA-N

物化性质

• 沸点：
  331.7±52.0 °C(Predicted)
• 密度：
  1.13±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  18
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  32.8
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  tert-butyl isoindolin-2-yl(methyl)carbamate 在 盐酸 、 1-羟基苯并三唑 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 、 N,N-二异丙基乙胺 作用下， 以 1,4-二氧六环 、 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 12.0h， 生成 N²-[5-chloro-2-(4-chlorophenoxy)phenyl]-N²-{2-[1,3-dihydro-2H-isoindol-2-yl(methyl)amino]-2-oxoethyl}-N¹-(2-pyrrolidin-1-ylethyl)glycinamide
  参考文献：
  名称：

  Discovery and structural analyses of S-adenosyl-l-homocysteine hydrolase inhibitors based on non-adenosine analogs

  摘要：

  Optimization of a new series of S-adenosyl-L-homocysteine hydrolase (AdoHcyase) inhibitors based on non-adenosine analogs led to very potent compounds 14n, 18a, and 18b with IC50 values of 13 +/- 3, 5.0 +/- 2.0, and 8.5 +/- 3.1 nM, respectively. An X-ray crystal structure of AdoHcyase with NAD(+) and 18a showed a novel open form co-crystal structure. 18a in the co-crystals formed intramolecular eight membered ring hydrogen bond formations. A single crystal X-ray structure of 14n also showed an intramolecular eight-membered ring hydrogen bond interaction. (C) 2015 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2015.05.018
• 作为产物：
  描述：

  二碳酸二叔丁酯 在 三乙胺 作用下， 以 N-甲基吡咯烷酮 、 乙醇 、 二氯甲烷 为溶剂， 生成 tert-butyl isoindolin-2-yl(methyl)carbamate
  参考文献：
  名称：

  Discovery and structural analyses of S-adenosyl-l-homocysteine hydrolase inhibitors based on non-adenosine analogs

  摘要：

  Optimization of a new series of S-adenosyl-L-homocysteine hydrolase (AdoHcyase) inhibitors based on non-adenosine analogs led to very potent compounds 14n, 18a, and 18b with IC50 values of 13 +/- 3, 5.0 +/- 2.0, and 8.5 +/- 3.1 nM, respectively. An X-ray crystal structure of AdoHcyase with NAD(+) and 18a showed a novel open form co-crystal structure. 18a in the co-crystals formed intramolecular eight membered ring hydrogen bond formations. A single crystal X-ray structure of 14n also showed an intramolecular eight-membered ring hydrogen bond interaction. (C) 2015 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2015.05.018

文献信息

• THERAPEUTIC AGENT FOR CEREBRAL INFARCTION
  申请人：Nakao Akira

  公开号：US20120196824A1

  公开（公告）日：2012-08-02

  The invention provides a therapeutic drug for ischemic stroke. The therapeutic drug has the formula (I) wherein each symbol is as defined herein, or a pharmacologically acceptable salt thereof, or a solvate thereof, as an active ingredient.

  这项发明提供了一种用于缺血性中风的治疗药物。该治疗药物具有如下式（I）的化学式，其中每个符号如本文所定义，或其药理学上可接受的盐，或其溶剂化物，作为活性成分。
• Design and Synthesis of Amide Derivatives as <i>S</i>-Adenosyl-L-Homocysteine Hydrolase Inhibitors
  作者：Xiangduan Tan、Panfeng Wang、Siyun Nian、Guoping Wang

  DOI：10.1248/cpb.c13-00623

  日期：——

  In this study, a series of amide derivatives were synthesized and evaluated for their S-adenosyl-L-homocysteine hydrolase (SAHase) inhibitory activities. The results demonstrated that most of compounds displayed potent SAHase inhibitory activities. Interestingly, compounds 11 and 14 exhibited more potent inhibitory effects than the aristeromycin, one of the most potent SAHase inhibitors known so far. Compounds 12, 13, 15 and 17 exhibited a moderate effect (IC50<10.0 µM). The structure–activity relationship found that compounds with substituted indazole-5-yl group at Ar position and ethylamino group at the side chain showed better SAHase inhibitory activities.

  在本研究中，合成了一系列酰胺衍生物，并评估了其对S-腺苷- L-半胱氨酸水解酶（SAHase）的抑制活性。结果表明，大多数化合物表现出良好的SAHase抑制活性。有趣的是，化合物11和14的抑制效果比已知的最强SAHase抑制剂之一阿利斯霉素更强。化合物12、13、15和17表现出中等效应（IC50<10.0 µM）。结构-活性关系研究发现，在Ar位具有取代的吡唑-5-基团和侧链中的乙基氨基团的化合物显示出更好的SAHase抑制活性。
• Arylthioureidoisoindolines and use as plant growth regulators
  申请人：Gulf Oil Corporation

  公开号：US04272284A1

  公开（公告）日：1981-06-09

  A novel class of compounds which are useful as plant growth regulators has the general structural formula ##STR1## in which R is H or CH.sub.3, R' is halogen, trifluoromethyl, cyano or C.sub.1 to C.sub.3 alkyl or alkoxy and n is zero or an integer from 1 to 2. The compounds are synthesized by reacting a compound of the formula ##STR2## with an isocyanate of the formula ##STR3## under basic conditions in a non-reactive, polar organic solvent.

  一类新型化合物，可用作植物生长调节剂，其一般结构式为##STR1##其中，R为H或CH.sub.3，R'为卤素、三氟甲基、氰基或C.sub.1到C.sub.3烷基或烷氧基，n为零或1到2的整数。这些化合物通过在非反应性、极性有机溶剂中，在碱性条件下将式##STR2##的化合物与式##STR3##的异氰酸酯反应合成。
• Arylthioureidoisoindolines
  申请人：Gulf Oil Corporation

  公开号：US04321200A1

  公开（公告）日：1982-03-23

  A novel class of compounds which are useful as plant growth regulators has the general structural formula ##STR1## in which R is H or CH.sub.3, R' is halogen, trifluoromethyl, cyano or C.sub.1 to C.sub.3 alkyl or alkoxy and n is zero or an integer from 1 to 2. The compounds are synthesized by reacting a compound of the formula ##STR2## with an isocyanate of the formula ##STR3## under basic conditions in a non-reactive, polar organic solvent.

  一种新型的化合物类，可用作植物生长调节剂，其一般结构式为##STR1## 其中R为H或CH.sub.3，R'为卤素、三氟甲基、氰基或C.sub.1到C.sub.3烷基或烷氧基，n为零或1至2的整数。这些化合物是通过在非反应性极性有机溶剂中，在碱性条件下将式##STR2##的化合物与式##STR3##的异腈反应合成的。
• Homocysteine synthase inhibitor
  申请人：Nakao Akira

  公开号：US08513235B2

  公开（公告）日：2013-08-20

  The invention provides a homocysteine synthase inhibitor useful for the prophylaxis or treatment of diseases involving homocysteine synthase. The homocysteine synthase inhibitor is a compound of the formula (I) wherein each symbol is as defined herein, or a pharmacologically acceptable salt thereof, or a solvate thereof.

  本发明提供了一种对于预防或治疗涉及到同型半胱氨酸合酶的疾病有用的同型半胱氨酸合酶抑制剂。该同型半胱氨酸合酶抑制剂是式(I)的化合物，其中每个符号如本文所定义，或其药理学可接受的盐，或其溶剂化物。