methyl 4-chloro-2-isothiocyanatobenzoate | 342623-34-1

• 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-chloro-2-isothiocyanatobenzoate
• CAS: 342623-34-1
• 化学式: C₉H₆ClNO₂S
• mdl: MFCD22557682
• 分子量: 227.671
• InChiKey: MNDBTUUTHIRHNU-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.8
• 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 4-chloro-2-isothiocyanatobenzoate 在 吡啶 、 氨 作用下， 以 甲苯 为溶剂， -34.0~20.0 ℃ 、200.0 kPa 条件下， 反应 1.0h， 以93%的产率得到7-氯-2-巯基喹唑啉-4(3H)-酮
  参考文献：
  名称：

  Conversion of 2-Thioxo-2,3-dihydroquinazolin-4(1H)-ones to N(3)-Unsubstituted 2-(Het)Arylquinazolin-4(3H)-ones by Copper-Mediated Pd-Catalysed Cross-Coupling Reactions

  摘要：

  With the purpose of searching for new heterocyclic building blocks, a new method to access N(3)-unsubstituted 2-(het)arylquinazolin-4(3H)-ones from 2-thioxo-2,3-dihydroquinazolin-4(1H)-one derivatives was developed. The synthetic protocol was based on the copper-mediated palladium-catalysed cross-coupling reactions of 2-thioxo-2,3-dihydroquinazolin-4(1H)-ones with (het)arylstannanes or their S-benzylated derivatives with (het)arylboronic acids, using CuBr center dot Me2S and CuMeSal as promoters, respectively. A similar transformation was applied for the preparation of 2-aryl[ 1]benzothieno[3,2-d]pyrimidin-4(3H)-ones.

  DOI：

  10.3987/com-15-s(t)12
• 作为产物：
  描述：

  甲基2-胺-4-氯苯酚酯 、 硫光气 在 碳酸氢钠 作用下， 以 二氯甲烷 、 水 为溶剂， 以70%的产率得到methyl 4-chloro-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

• Isothiazoles as active-site inhibitors of HCV NS5B polymerase
  作者：Shunqi Yan、Todd Appleby、Esmir Gunic、Jae Hoon Shim、Tania Tasu、Hongwoo Kim、Frank Rong、Huaming Chen、Robert Hamatake、Jim Z. Wu、Zhi Hong、Nanhua Yao

  DOI：10.1016/j.bmcl.2006.10.002

  日期：2007.1

  Isothiazole analogs were discovered as a novel class of active-site inhibitors of HCV NS5B polymerase. The best compound has an IC(50) of 200 nM and EC(50) of 100 nM, which is a significant improvement over the starting inhibitor (1). The X-ray complex structure of 1 with HCV NS5B was obtained at a resolution of 2.2A, revealing that the inhibitor is covalently linked with Cys 366 of the 'primer-grip'. Furthermore, it makes considerable contacts with the C-terminus, beta-loop, and more importantly, to the active-site of the enzyme. The uniqueness of this binding mode offers a new insight for the rational design of novel inhibitors for HCV NS5B polymerase.
• KIENZLE, F.;KAISER, A.;MINDER, R. E., HELV. CHIM. ACTA, 1983, 66, N 1, 148-157
  作者：KIENZLE, F.、KAISER, A.、MINDER, R. E.

  DOI：——

  日期：——
• KABBE H.-J., J. LIEBIGS ANN. CHEM., 1978, NO 3, 398-404
  作者：KABBE H.-J.

  DOI：——

  日期：——
• Novel Thioxothiazolo[3,4-<i>a</i>]quinazolin-5(4<i>H</i>)-one Derivatives as BK_Ca Channel Activators for Urinary Incontinence
  作者：Eun Jung Bae、Heeji Jo、Seong Soon Kim、Dae-Seop Shin、Jung Yoon Yang、Myung Ae Bae、Pyeonghwa Jeong、Chul-Seung Park、Jin Hee Ahn

  DOI：10.1021/acsmedchemlett.2c00070

  日期：2022.7.14
• [EN] PHARMACEUTICAL COMPOSITION FOR PREVENTING OR TREATING OVERACTIVE BLADDER<br/>[FR] COMPOSITION PHARMACEUTIQUE DE PRÉVENTION OU DE TRAITEMENT D'UNE VESSIE HYPERACTIVE<br/>[KO] 과민성 방광의 예방 또는 치료용 약학 조성물
  申请人：[en]GWANGJU INSTITUTE OF SCIENCE AND TECHNOLOGY;[ko]광주과학기술원

  公开号：WO2023113114A1

  公开（公告）日：2023-06-22

  본 발명은 BKCa채널을 활성화시키는 신규한 퀴나졸린 계열 화합물 및 이의 과민성 방광의 예방 또는 치료 용도에 관한 것이다. 본 발명의 화합물들은 BKCa채널을 효과적으로 활성화시킬 수 있어, BKCa채널 비활성화 또는 활성 저하에 따라 발생하는 과민성 방광의 예방 또는 치료에 이용될 수 있다.