tert-butyl {4-[(1,3-thiazol-2-ylamino)carbonyl]phenyl}carbamate | 851202-69-2

• 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: tert-butyl {4-[(1,3-thiazol-2-ylamino)carbonyl]phenyl}carbamate
• 英文别名: tert-butyl N-[4-(1,3-thiazol-2-ylcarbamoyl)phenyl]carbamate
• CAS: 851202-69-2
• 化学式: C₁₅H₁₇N₃O₃S
• 分子量: 319.384
• InChiKey: HXRJEBWSRDDKHF-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  22
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.27
• 拓扑面积：
  109
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  tert-butyl {4-[(1,3-thiazol-2-ylamino)carbonyl]phenyl}carbamate 在 盐酸 、 水 、 sodium hydroxide 作用下， 以 1,4-二氧六环 为溶剂， 反应 24.17h， 生成 4-(ethanimidoylamino)-N-1,3-thiazol-2-ylbenzamide hydrobromide
  参考文献：
  名称：

  Antiglioma Activity of Aryl and Amido-Aryl Acetamidine Derivatives Targeting iNOS: Synthesis and Biological Evaluation

  摘要：

  Nitric oxide is an important inflammation mediator with a recognized role in the development of different cancers. Gliomas are primary tumors of the central nervous system with poor prognosis, and the expression of the inducible nitric oxide synthase correlates with the degree of malignancy, changes in vascular reactivity, and neo-angiogenesis. Therefore, targeting the nitric oxide biosynthesis appears as a potential strategy to impair glioma progression. In the present work a set of aryl and amido-aryl acetamidine derivatives were synthesized to obtain new potent and selective inducible nitric oxide synthase inhibitors with improved physicochemical parameters with respect to the previously published molecules. Compound 17 emerged as the most promising inhibitor and was evaluated on C6 rat glioma cell line, showing antiproliferative effects and high selectivity over astrocytes.

  DOI：

  10.1021/acsmedchemlett.0c00285
• 作为产物：
  描述：

  二碳酸二叔丁酯 在 1-羟基苯并三唑 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 、 sodium hydroxide 作用下， 以 1,4-二氧六环 、 水 、 N,N-二甲基甲酰胺 为溶剂， 反应 96.0h， 生成 tert-butyl {4-[(1,3-thiazol-2-ylamino)carbonyl]phenyl}carbamate
  参考文献：
  名称：

  寨卡病毒抑制剂新系列N-酰基-2-氨基苯并噻唑的发现及结构优化

  摘要：

  寨卡病毒感染与先天性小头畸形和寨卡热等严重疾病有关，对人类造成严重伤害，特别引起低收入国家卫生系统的关注。目前，尚无针对该病毒的批准药物，因此开发抗寨卡病毒药物刻不容缓。目前的研究描述了抗寨卡病毒复制的N-酰基-2-氨基苯并噻唑系列化合物的发现和命中扩展。通过合成和评价 19 种衍生物的抗寨卡病毒活性和对 Vero 细胞的细胞毒性，获得了构效关系研究。三种优化化合物的效力比初始化合物强 2.2 倍，选择性分别高 20.9、7.7 和 6.4 倍。随后进行表型和生化测定，以证明非结构蛋白（例如复合物 NS2B-NS3pro）是否与最活性化合物的作用机制有关。

  DOI：

  10.1016/j.bmc.2023.117488

文献信息

• [EN] N-THIAZOL-2-YL-BENZAMIDE DERIVATIVES<br/>[FR] DERIVES DE N-THIAZOLE-2-YLE-BENZAMIDE
  申请人：LUNDBECK & CO AS H

  公开号：WO2005039572A1

  公开（公告）日：2005-05-06

  The invention relates to N-thiazol-2-yl-benzamide derivatives of the formula I in the description wherein the variables are as defined in the claims. The compounds are A2A-receptor ligands, such as antagonists, agonists, reverse agonists or partial agonists, and are useful in the treatment of neurological and psychiatric disorders where an A2A-receptor is implicated.

  该发明涉及描述中的式I的N-噻唑-2-基苯甲酰衍生物，其中变量如索权中所定义。这些化合物是A2A受体配体，如拮抗剂、激动剂、反向激动剂或部分激动剂，并且在治疗神经和精神障碍中具有用处，其中A2A受体被牵涉其中。
• N-thiazol-2-yl-benzamide derivatives
  申请人：Sams Graven Anette

  公开号：US20060154974A1

  公开（公告）日：2006-07-13

  The invention relates to compounds of the formula I wherein the variables are as defined in the claims. The compounds are A 2A -receptor ligands, such as antagonists, agonists, reverse agonists or partial agonists, and are useful in the treatment of neurological and psychiatric disorders where an A 2A -receptor is implicated.

  本发明涉及公式I的化合物，其中变量如权利要求所定义。该化合物是A2A受体配体，如拮抗剂，激动剂，反向激动剂或部分激动剂，并且在治疗涉及A2A受体的神经和精神障碍方面有用。
• N-THIAZOL-2-YL-BENZAMIDE DERIVATIVES
  申请人：Sams Anette Graven

  公开号：US20090247593A1

  公开（公告）日：2009-10-01

  The invention relates to compounds of the formula I wherein the variables are as defined in the claims. The compounds are A 2A -receptor ligands, such as antagonists, agonists, reverse agonists or partial agonists, and are useful in the treatment of neurological and psychiatric disorders where an A 2A -receptor is implicated.

  本发明涉及式I的化合物，其中变量如权利要求所定义。这些化合物是A2A受体配体，例如拮抗剂、激动剂、反向激动剂或部分激动剂，并且在治疗神经系统和精神障碍中，其中涉及到A2A受体时具有用处。
• Antiglioma Activity of Aryl and Amido-Aryl Acetamidine Derivatives Targeting iNOS: Synthesis and Biological Evaluation
  作者：Cristina Maccallini、Fabio Arias、Marialucia Gallorini、Pasquale Amoia、Alessandra Ammazzalorso、Barbara De Filippis、Marialuigia Fantacuzzi、Letizia Giampietro、Amelia Cataldi、María Encarnación Camacho、Rosa Amoroso

  DOI：10.1021/acsmedchemlett.0c00285

  日期：2020.7.9

  Nitric oxide is an important inflammation mediator with a recognized role in the development of different cancers. Gliomas are primary tumors of the central nervous system with poor prognosis, and the expression of the inducible nitric oxide synthase correlates with the degree of malignancy, changes in vascular reactivity, and neo-angiogenesis. Therefore, targeting the nitric oxide biosynthesis appears as a potential strategy to impair glioma progression. In the present work a set of aryl and amido-aryl acetamidine derivatives were synthesized to obtain new potent and selective inducible nitric oxide synthase inhibitors with improved physicochemical parameters with respect to the previously published molecules. Compound 17 emerged as the most promising inhibitor and was evaluated on C6 rat glioma cell line, showing antiproliferative effects and high selectivity over astrocytes.
• Discovery and structural optimization of a new series of N-acyl-2-aminobenzothiazole as inhibitors of Zika virus
  作者：Renieidy Flávia Clemente Dias、Beatriz Murta Rezende Moraes Ribeiro、Natasha Marques Cassani、Danilo Nascimento Farago、Giovanna André Antoniucci、Rafael Eduardo de Oliveira Rocha、Felipe de Oliveira Souza、Eduardo Jorge Pilau、Ana Carolina Gomes Jardim、Rafaela Salgado Ferreira、Celso de Oliveira Rezende Júnior

  DOI：10.1016/j.bmc.2023.117488

  日期：2023.11

  countries. Currently, there are no approved drugs against the virus, and the development of anti-Zika virus drugs is thus urgent. The present investigation describes the discovery and hit expansion of a N-acyl-2-aminobenzothiazole series of compounds against Zika virus replication. A structure–activity relationship study was obtained with the synthesis and evaluation of anti-Zika virus activity and cytotoxicity

  寨卡病毒感染与先天性小头畸形和寨卡热等严重疾病有关，对人类造成严重伤害，特别引起低收入国家卫生系统的关注。目前，尚无针对该病毒的批准药物，因此开发抗寨卡病毒药物刻不容缓。目前的研究描述了抗寨卡病毒复制的N-酰基-2-氨基苯并噻唑系列化合物的发现和命中扩展。通过合成和评价 19 种衍生物的抗寨卡病毒活性和对 Vero 细胞的细胞毒性，获得了构效关系研究。三种优化化合物的效力比初始化合物强 2.2 倍，选择性分别高 20.9、7.7 和 6.4 倍。随后进行表型和生化测定，以证明非结构蛋白（例如复合物 NS2B-NS3pro）是否与最活性化合物的作用机制有关。