methyl 4-(isothiocyanatomethyl)benzoate | 35009-16-6

• 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: methyl 4-(isothiocyanatomethyl)benzoate
• CAS: 35009-16-6
• 化学式: C₁₀H₉NO₂S
• 分子量: 207.253
• InChiKey: YTHYVSUCHOMEPK-UHFFFAOYSA-N

物化性质

• 沸点：
  334.7±25.0 °C(Predicted)
• 密度：
  1.14±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.7
• 重原子数：
  14
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.2
• 拓扑面积：
  70.8
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  methyl 4-(isothiocyanatomethyl)benzoate 在 氨 作用下， 以 二氯甲烷 为溶剂， 反应 3.5h， 以99%的产率得到methyl 4-(thioureidomethyl)benzoate
  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：

  4-氯甲基苯甲酰氯 在 sodium hydroxide 、 乙醇 作用下， 生成 methyl 4-(isothiocyanatomethyl)benzoate
  参考文献：
  名称：

  Some Esters Based on p-Chloromethylbenzoyl Chloride

  摘要：

  DOI：

  10.1021/ja01167a097

文献信息

• Heterocyclic modulators of nuclear receptors
  申请人：——

  公开号：US20030212111A1

  公开（公告）日：2003-11-13

  Compounds, compositions and methods for modulating the activity of nuclear receptors are provided. In particular, heterocyclic compounds are provided for modulating the activity of farnesoid X receptor (FXR), liver X receptor (LXR) and/or orphan nuclear receptors. In certain embodiments, the compounds are thiazolidinone derivatives.

  提供了用于调节核受体活性的化合物、组合物和方法。具体来说，提供了用于调节法尼索醇X受体（FXR）、肝X受体（LXR）和/或孤儿核受体活性的杂环化合物。在某些实施例中，这些化合物是噻唑啉酮衍生物。
• New Mild and Simple Approach to Isothiocyanates: A Class of Potent Anticancer Agents
  作者：Bingling Luo、Jiankang Wang、Xiaobing Li、Wenhua Lu、Jing Yang、Yumin Hu、Peng Huang、Shijun Wen

  DOI：10.3390/molecules22060773

  日期：——

  In our current work, acetyl chloride-mediated synthesis of phenethyl isothiocyanate (PEITC) derivatives proves to be convenient and provides the expected products at good to excellent yields. Biological evaluation and structure-activity relationship analysis found that the novel compound 7 showed the best anticancer activity against human cancer cell line Panc1 and HGC27 compared with PEITC. Compounds

  在我们目前的工作中，乙酰氯介导的异硫氰酸苯乙酯 (PEITC) 衍生物合成被证明是方便的，并以良好的收率提供预期的产品。生物学评价和构效关系分析发现，与PEITC相比，新型化合物7对人癌细胞系Panc1和HGC27的抗癌活性最好。化合物 6 和 7 在胰腺癌细胞中诱导更多的细胞凋亡，但在非癌细胞中的毒性较小。进一步的生物学研究表明，7 种细胞内活性氧 (ROS) 和耗尽型谷胱甘肽 (GSH) 显着增加，导致氧化应激杀死癌细胞。
• Chemical compounds
  申请人：——

  公开号：US20040116458A1

  公开（公告）日：2004-06-17

  Compounds of the general structural formula 1 and use of the compounds and salts and solvates thereof, as therapeutic agents.

  一般结构式1的化合物及其盐和溶剂化合物的用途，作为治疗剂。
• NOVEL DERIVATIVES OF BENZIMIDAZOLE AND IMIDAZO-PYRIDINE AND THEIR USE AS MEDICAMENTS
  申请人：POITOUT Lydie

  公开号：US20090270372A1

  公开（公告）日：2009-10-29

  A subject of the present Application is novel derivatives of benzimidazole and imidazopyridine which have a good affinity for certain sub-types of melanocortin receptors, in particular the MC4 receptors. They are particularly useful for treating pathological conditions and diseases in which one or more melanocortin receptors are involved. The invention also relates to pharmaceutical compositions containing said products.

  本申请的主题是苯并咪唑和咪唑吡啶的新衍生物，它们对于某些亚型的黑色素皮质素受体，特别是MC4受体具有良好的亲和力。它们特别适用于治疗涉及一个或多个黑色素皮质素受体的病理条件和疾病。本发明还涉及含有上述产物的制药组合物。
• 10.1021/acs.jmedchem.4c00477
  作者：Carullo, Gabriele、Orsini, Noemi、Piano, Ilaria、Pozzetti, Luca、Papa, Alessandro、Fontana, Anna、Napoli, Debora、Corsi, Francesca、Marco, Beatrice Di、Galante, Alessia、Marotta, Ludovica、Panzeca, Giovanna、O’Brien, Justine、Sanchez, Alicia Gomez、Doherty, Harry、Mahon, Niamh、Clarke, Leni、Contri, Chiara、Pasquini, Silvia、Gorelli, Beatrice、Saponara, Simona、Valoti, Massimo、Vincenzi, Fabrizio、Varani, Katia、Ramunno, Anna、Brogi, Simone、Butini, Stefania、Gemma, Sandra、Kennedy, Breandán N.、Gargini, Claudia、Strettoi, Enrica、Campiani, Giuseppe

  DOI：10.1021/acs.jmedchem.4c00477

  日期：——

  Inherited retinal diseases, which include retinitis pigmentosa, are a family of genetic disorders characterized by gradual rod-cone degeneration and vision loss, without effective pharmacological treatments. Experimental approaches aim to delay disease progression, supporting cones’ survival, crucial for human vision. Histone deacetylases (HDACs) mediate the activation of epigenetic and nonepigenetic

  遗传性视网膜疾病，包括色素性视网膜炎，是一类遗传性疾病，其特征是逐渐的视锥细胞变性和视力丧失，且没有有效的药物治疗。实验方法旨在延缓疾病进展，支持视锥细胞的生存，这对人类视觉至关重要。组蛋白脱乙酰酶 (HDAC) 介导表观遗传和非表观遗传途径的激活，从而调节 RP 小鼠模型中的视锥细胞变性。我们开发了新的 HDAC 抑制剂 ( 5a – p )，以四氢-γ-咔啉支架为代表，其特点是具有高 HDAC6 抑制效力和平衡的理化特性，适合体内研究。与 ARPE-19 和 661W 细胞中的组蛋白 H3 相比，化合物5d （ repistat ，IC 50 HDAC6 = 6.32 nM）增加了乙酰化 α-微管蛋白的水平。 5d促进了atp6v0e1 –/–光感受器功能障碍斑马鱼模型的视力挽救。在 RP rd10小鼠模型中单次玻璃体内注射5d支持视锥细胞的形态和功能保存以及视网膜色素上皮阵列的维持。