m-Nitrobenzylisothiocyanat | 3696-69-3

• 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: m-Nitrobenzylisothiocyanat
• 英文别名: 1-(Isothiocyanatomethyl)-3-nitrobenzene
• CAS: 3696-69-3
• 化学式: C₈H₆N₂O₂S
• 分子量: 194.214
• InChiKey: YBULXORMKBLKEP-UHFFFAOYSA-N

物化性质

• 密度：
  1.3861 (rough estimate)

计算性质

• 辛醇/水分配系数(LogP)：
  3.4
• 重原子数：
  13
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  90.3
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  m-Nitrobenzylisothiocyanat 在 氨 、 tin(ll) chloride 作用下， 以 乙醇 、 二氯甲烷 为溶剂， 反应 6.5h， 生成 N-(3-aminobenzyl)thiourea
  参考文献：
  名称：

  Synthesis of N-benzyl- and N-phenyl-2-amino-4,5-dihydrothiazoles and thioureas and evaluation as modulators of the isoforms of nitric oxide synthase

  摘要：

  Inhibition of the isoforms of nitric oxide synthase (NOS) has important applications in therapy of several diseases, including cancer. Using 1400W [N-(3-aminomethylbenzyl)acetamidme], thiocitrulline and N-delta-(4,5-dihydrothiazol-2-yl)ornithine as lead compounds, series of N-benzyl- and N-phenyl-2-amino-4,5-dihydrothiazoles and thioureas were designed as inhibitors of NOS. Ring-substituted benzyl and phenyl isothiocyanates were synthesised by condensation of the corresponding amines with thiophosgene and addition of ammonia gave the corresponding thioureas in high yields. The substituted 2-amino-4,5-dihydrothiazoles were approached by two routes. Treatment of simple benzylamines with 2-methylthio-4,5-dihydrothiazole at 180degreesC afforded the corresponding 2-benzylamino-4,5-dihydrothiazoles. For less nucleophilic amines and those carrying more thermally labile substituents, the 4,5-dihydrothiazoles were approached by acid-catalysed cyclisation of N-(2-hydroxyethyl)thioureas. This cyclisation was shown to proceed by an S(N)2-like process. Modest inhibitory activity was shown by most of the thioureas and 4,5-dihydrothiazoles, with N-(3-aminomethylphenyl)thiourea (IC50 = 13 muM vs rat neuronal NOS and IC50 = 23 muM vs rat inducible NOS) and 2-(3-aminomethylphenylamino)-4,5-dihydrothiazole (IC50 - 13 muM vs rat neuronal NOS and IC50 = 19 muM vs human inducible NOS) being the most potent. Several thioureas and 4,5-dihydrothiazoles were found to stimulate the activity of human inducible NOS in a time-dependent manner. (C) 2003 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/s0968-0896(03)00451-6
• 作为产物：
  描述：

  3-硝基苄胺 在 氢氧化钾 作用下， 以 水 为溶剂， 生成 m-Nitrobenzylisothiocyanat
  参考文献：
  名称：

  Hirashima, Akinori; Yoshii, Yutaka; Eto, Morifusa, Bioscience, Biotechnology and Biochemistry, 1992, vol. 56, # 7, p. 1062 - 1065

  摘要：

  DOI：

文献信息

• Differentiating Antiproliferative and Chemopreventive Modes of Activity for Electron-Deficient Aryl Isothiocyanates against Human MCF-7 Cells
  作者：Ruthellen H. Anderson、Cody J. Lensing、Benjamin J. Forred、Michael W. Amolins、Cassandra L. Aegerter、Peter F. Vitiello、Jared R. Mays

  DOI：10.1002/cmdc.201800348

  日期：2018.8.20

  cancer cells, and 2) alter cellular transcriptional profiles. This study describes the preparation of a library of non‐natural aryl ITCs and the development of a bifurcated screening approach to evaluate the dose‐ and time‐dependence on antiproliferative and chemopreventive properties against human MCF‐7 breast cancer cells. Antiproliferative effects were evaluated using a commercial MTS cell viability

  食用芸苔属蔬菜通过有机异硫氰酸酯（ITC）（芥子油苷次生代谢物酶水解的产物）提供有益效果。ITC l-萝卜硫素 ( l -SFN) 是西兰花中的主要成分，具有多种抗癌作用。虽然l -SFN等 ITC 的抗癌特性已得到广泛研究，并且l -SFN 已成为多项人体临床试验的主题，但这项工作的范围在很大程度上仅限于自然界中发现的衍生物。先前的研究表明，ITC 的结构变化可能导致化合物功效显着差异：1) 抑制癌细胞生长，2) 改变细胞转录谱。本研究描述了非天然芳基 ITC 库的制备以及分叉筛选方法的开发，以评估针对人 MCF-7 乳腺癌细胞的抗增殖和化学预防特性的剂量和时间依赖性。使用商业 MTS 细胞活力测定来评估抗增殖作用。使用抗氧化反应元件（ARE）促进的荧光素酶报告基因测定评估化学预防特性。本研究的结果确定了 1) 几个关键的结构-活性关系和 2) 用于持续开发的主要 ITC。
• Antimicrobial activity of a series of aminoalkyl esters of benzyldithiocarbamic acids
  作者：Robert C. Tweit、Robert D. Muir、Seth Mizuba

  DOI：10.1021/jm00302a043

  日期：1969.3
• NITROGEN-CONTAINING FUSED HETEROCYCLIC COMPOUNDS
  申请人：Takeda Pharmaceutical Company Limited

  公开号：EP1677791A2

  公开（公告）日：2006-07-12
• EP1677791A4
  申请人：——

  公开号：EP1677791A4

  公开（公告）日：2007-08-15
• [EN] NITROGEN-CONTAINING FUSED HETEROCYCLIC COMPOUNDS<br/>[FR] COMPOSES HETEROCYCLIQUES ACCOLES CONTENANT DE L'AZOTE
  申请人：TAKEDA PHARMACEUTICAL

  公开号：WO2005044793A2

  公开（公告）日：2005-05-19

  There is provided a CRF receptor antagonist comprising a compound of the formula (I): wherein, ring A is a 5-membered ring represented by the formula (A'): wherein X is a carbon and X1 is an oxygen, a sulfur or - NR 5-, or formula (A'): wherein X is a nitrogen and R6 is an optionally substituted hydrocarbyl, R1 is an amino substituted by two optionally substituted hydrocarbyl groups, R2 is an phenyl, Y1 is CR3a or a nitrogen, Y2 is CR3b or a nitrogen and Y3 is CR3C or a nitrogen, provided that one or less of Y1, Y2, and Y3 is nitrogen, W is a bond, -(CH2)n-, and Z is a bond, -NR 4-, etc.; or a salt thereof or a prodrug thereof.