methyl 5-bromo-2-isothiocyanatobenzoate | 131842-27-8

• 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 5-bromo-2-isothiocyanatobenzoate
• CAS: 131842-27-8
• 化学式: C₉H₆BrNO₂S
• 分子量: 272.122
• InChiKey: BOVYMTDISMCWLI-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.9
• 重原子数：
  14
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.11
• 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 5-bromo-2-isothiocyanatobenzoate 在 copper(l) iodide 、 铜 、 potassium hydroxide 、 sodium hydroxide 作用下， 以 乙醇 、 二氯甲烷 、 水 为溶剂， 反应 13.0h， 生成 4-({6-bromo-3-[(methylsulfonyl)amino]-4-oxo-3,4-dihydroquinazolin-2-yl}thio)benzoic acid
  参考文献：
  名称：

  Synthesis, structure–activity relationships, and bioactivity evaluation of 6-bromo-quinazolinone derivatives

  摘要：

  6-Bromo-quinazolinone derivatives were prepared and evaluated for the ability to inhibit cyclooxygenase-2 (COX-2). An extensive structure-activity relationship work was carried out, thus some potent and selective COX-2 inhibitors were identified. The key compound isothiocyanate was prepared through a simple and ecological method using di-2-pyridyl thionocarbonate in substitution of the thiophosgene, a potential air pollutant. The cyclization reaction of intermediate derivatives was developed through the methods reporting by Wamhoff. The anti-inflammatory activity of the derivatives (5-12) was evaluated by determining (by Western blot) the expression of cyclooxygenase (COX)-2, of inducible NO synthase (iNOS) and of intercellular adhesion molecule-1 (ICAM-1). The biological assays showed that the derivatives 7, 9, 10, 12 act as potent inhibitors of COX-2, iNOS, and ICAM-1 expression in human keratinocytes NCTC-2544 cells. This work showed that the new derivatives could be used as a novel class of anti-inflammatory agents.

  DOI：

  10.1007/s00044-014-1311-7
• 作为产物：
  描述：

  硫光气 、 5-溴氨基苯甲酸甲酯 在 碳酸氢钠 作用下， 以 二氯甲烷 、 水 为溶剂， 以58%的产率得到methyl 5-bromo-2-isothiocyanatobenzoate
  参考文献：
  名称：

  通过高通量筛选鉴定新型融合杂芳基 MALT1 抑制剂治疗 B 细胞淋巴瘤

  摘要：

  黏膜相关淋巴组织淋巴瘤易位蛋白 1 (MALT1) 抑制剂的开发在肿瘤性疾病、炎症和自身免疫性疾病的治疗中具有重要价值和意义。然而，临床上缺乏有效的MALT1抑制剂。在此，首次通过高通量鉴定和设计了一类新型有效的 5-oxo-1-thioxo-4,5-dihydro-1 H - thiazolo[3,4- a ]quinazoline 抑制剂及其共价衍生物。筛选。我们证明了化合物15c、15e和20c有效抑制 MALT1 蛋白酶并对活化的 B 细胞样弥漫性大 B 细胞淋巴瘤具有低个位数微摩尔效力显示出选择性细胞毒性。此外，化合物20c以剂量依赖性方式特异性抑制 MALT1 依赖性 TMD8 细胞中的 NF-κB 信号传导并诱导细胞凋亡。更重要的是，20c在 TMD8 异种移植肿瘤模型中显示出良好的药代动力学特性和抗肿瘤功效，且无显着毒性。总的来说，这项研究为 MALT1 抑制剂的进一步结构

  DOI：

  10.1021/acs.jmedchem.1c00466

文献信息

• MODULATORS OF ACETYL-COENZYME A CARBOXYLASE AND METHODS OF USE THEREOF
  申请人：Anderson Richard

  公开号：US20080200461A1

  公开（公告）日：2008-08-21

  The present invention provides compounds of formula I: along with methods of use thereof for the control of agricultural pests, particularly fungal pests, weedy pests and insect pests, as well as use as pharmaceuticals, particularly the treatment of obesity, metabolic syndrome, atherosclerosis, cardiovascular disease and insulin resistance, e.g., type II or adult-onset diabetes as well as fungal pathogens of humans and animals

  本发明提供了公式I的化合物： 以及使用它们控制农业害虫的方法，尤其是真菌害虫、杂草害虫和昆虫害虫，以及用作药物，特别是治疗肥胖、代谢综合征、动脉硬化、心血管疾病和胰岛素抵抗的方法，例如II型或成年发病型糖尿病以及人类和动物的真菌病原体。
• [EN] QUINAZOLINONE DERIVATIVES AS ANTIVIRAL AGENTS<br/>[FR] DÉRIVÉS DE QUINAZOLINONE EN TANT QU'AGENTS ANTIVIRAUX
  申请人：GLAXOSMITHKLINE LLC

  公开号：WO2012087938A1

  公开（公告）日：2012-06-28

  Provided are compounds and pharmaceutically acceptable salts thereof, their pharmaceutical compositions, their methods of preparation, and their use for treating viral infections mediated by a member of the Flaviviridae family of viruses such as hepatitis C virus (HCV).

  提供了化合物及其药用盐，它们的药物组合物，它们的制备方法，以及它们用于治疗由黄病毒科（Flaviviridae）家族成员介导的病毒感染，如丙型肝炎病毒（HCV）的用途。
• Graefe, I.; Kottke, K.; Kuehmstedt, H., Pharmazie, 1990, vol. 45, # 7, p. 530 - 531
  作者：Graefe, I.、Kottke, K.、Kuehmstedt, H.、Knoke, Dagmar

  DOI：——

  日期：——
• Microwave-Mediated Heterocyclization to Benzimidazo[2,1-<i>b</i>]quinazolin-12(5<i>H</i>)-ones
  作者：Richard D. Carpenter、Kit S. Lam、Mark J. Kurth

  DOI：10.1021/jo0618066

  日期：2007.1.1

  An effective route to benzimidazo[2,1-b]quinazolin-12(5H)-ones from commercially available o-aryl isothiocyanate esters and o-phenylenediamines is reported. This method accommodates a variety of substituents on either starting material and proceeds under microwave irradiation in the presence of barium hydroxide, conditions that do not hydrolyze methyl ester substituents. The pharmacologically pertinent benzimidazoquinazolinone heterocycle is delivered in excellent yield and purity via both solution- and solid-phase protocols, the latter involving traceless release from the resin.
• Santagati; Modica; Santagati, Pharmazie, 2000, vol. 55, # 10, p. 737 - 740
  作者：Santagati、Modica、Santagati、Cutuli、Mangano、Caruso

  DOI：——

  日期：——