2-(hydrazinecarbonyl)-7-nitro-5-(trifluoromethyl)benzothiazole 3-oxide | 40646-82-0

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并噻唑类
• 英文名称: 2-(hydrazinecarbonyl)-7-nitro-5-(trifluoromethyl)benzothiazole 3-oxide
• 英文别名: 7-nitro-3-oxy-5-trifluoromethyl-benzothiazole-2-carboxylic acid hydrazide；7-Nitro-3-oxy-5-trifluoromethyl-benzothiazole-2-carboxylic acid hydrazide；7-nitro-3-oxido-5-(trifluoromethyl)-1,3-benzothiazol-3-ium-2-carbohydrazide
• CAS: 40646-82-0
• 化学式: C₉H₅F₃N₄O₄S
• 分子量: 322.224
• InChiKey: LKFDFEIBRPDFTC-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.2
• 重原子数：
  21
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.11
• 拓扑面积：
  155
• 氢给体数：
  2
• 氢受体数：
  9

反应信息

• 作为产物：
  描述：

  4-氯-3,5-二硝基三氟甲苯 在 ammonium hydroxide 、 三乙胺 、 肼 作用下， 以 乙醇 为溶剂， 反应 4.0h， 生成 2-(hydrazinecarbonyl)-7-nitro-5-(trifluoromethyl)benzothiazole 3-oxide
  参考文献：
  名称：

  迈森海默复合体作为药物发现的范例：通过C67的PLK1 ATP结合位点可逆共价抑制。

  摘要：

  polo激酶家族是重要的肿瘤学靶标，其在调节有丝分裂的进入和通过有丝分裂中起作用。描述了结构导向的新型Polo样激酶1（PLK1）催化活性抑制剂的发现，该抑制剂与ATP结合位点的Cys67相互作用。含有苯并噻唑N-氧化物骨架的化合物不仅与该残基共价结合，而且通过形成迈森海默络合物而成为可逆的抑制剂。激酶抑制的这种机制导致化合物可以高选择性地靶向PLK1，同时避免了不可逆的共价结合以及与细胞中其他含巯基分子相互作用的问题。由于对共价药物的兴趣重新出现，并且潜在的药物靶标过多，

  DOI：

  10.1016/j.chembiol.2018.06.001

文献信息

• [EN] BENZTHIAZOLE-3 OXIDES USEFUL FOR THE TREATMENT OF PROLIFERATIVE DISORDERS<br/>[FR] OXYDES DE BENZOTHIAZOLE-3 UTILES POUR LE TRAITEMENT DE TROUBLES PROLIFERATIFS
  申请人：CYCLACEL LTD

  公开号：WO2004067000A1

  公开（公告）日：2004-08-12

  The present invention relates to the use of a compound of formula (I), or a pharmaceutically acceptable salt thereof, wherein R1, R2, R3, and R4 are each independently H, N02, CF3, SCF3, CN, halo, OH, OR6, NH2, NHR6, NR6R7, N+R6R7R8, COOH, COOR6, CONH2, CONHR6, CONR6R7, COH, CORE, SR', SORE, S02R6, SO2OH, SO2OR6, S02NH2, S02NHR6, S02NR6R7, alkyl, cycloalkyl, cycloheteroalkyl, aryl, or heteroaryl, with the proviso that at least one of R1, R2, R3, and R4 is other than H; or R1 and R2, R2 and R3, or R3 and R4, may together form part of a fused or unfused saturated or unsaturated ring system, optionally containing up to two heteroatoms selected from N, 0, and S; R5 is OH, OR9, CN, CONH2, CONHNH2, CONHOH, CONHR9, CONR9R10, NH2, NHR9, or NR9R10; each R6, R7 and R8 is independently hydrocarbyl, or two of R6, R7 and R8 together form part of a saturated or unsaturated ring system, optionally containing up to two heteroatoms selected from N, 0, and S; each R9 and R10 is independently hydrocarbyl, or R9 and R10 together form part of a saturated or unsaturated ring system, optionally containing up to two heteroatoms selected from N, 0, and S; in the preparation of a medicament for treating a proliferative disorder.

  本发明涉及使用式(I)化合物或其药学上可接受的盐，其中R1、R2、R3和R4各自独立地为H、N02、CF3、SCF3、CN、卤素、OH、OR6、NH2、NHR6、NR6R7、N+R6R7R8、COOH、COOR6、CONH2、CONHR6、CONR6R7、COH、CORE、SR'、SORE、S02R6、SO2OH、SO2OR6、S02NH2、S02NHR6、S02NR6R7、烷基、环烷基、环杂烷基、芳基或杂芳基，但至少有一个R1、R2、R3和R4不是H；或者R1和R2、R2和R3或R3和R4可以共同形成融合或未融合的饱和或不饱和环系的一部分，可选地含有最多两个从N、0和S中选择的杂原子；R5为OH、OR9、CN、CONH2、CONHNH2、CONHOH、CONHR9、CONR9R10、NH2、NHR9或NR9R10；每个R6、R7和R8独立地为烃基，或者R6、R7和R8中的两个共同形成饱和或不饱和环系的一部分，可选地含有最多两个从N、0和S中选择的杂原子；每个R9和R10独立地为烃基，或者R9和R10共同形成饱和或不饱和环系的一部分，可选地含有最多两个从N、0和S中选择的杂原子；用于制备治疗增生性疾病的药物。
• Wagner,K. et al., Chemische Berichte, 1973, vol. 106, p. 640 - 654
  作者：Wagner,K. et al.

  DOI：——

  日期：——
• BENZTHIAZOLE-3 OXIDES USEFUL FOR THE TREATMENT OF PROLIFERATIVE DISORDERS
  申请人：Cyclacel Limited

  公开号：EP1589967B1

  公开（公告）日：2007-05-09
• JP2006518361A
  申请人：——

  公开号：JP2006518361A

  公开（公告）日：2006-08-10
• Benzthiazole-3 oxides useful for the treatment of proliferative disorders
  申请人：McInnes Campbell

  公开号：US20060040997A1

  公开（公告）日：2006-02-23

  The present invention relates to the use of a compound of formula I, or a pharmaceutically acceptable salt thereof, wherein R 1 , R 2 , R 3 , and R 4 are each independently H, NO 2 , CF 3 , SCF 3 , CN, halo, OH, OR 6 , NH 2 , NHR 6 , NR 6 R 7 , N + R 6 R 7 R 8 , COOH, COOR 6 , CONH 2 , CONHR 6 , CONR 6 R 7 , COH, COR 6 , SR 6 , SOR 6 , SO 2 R 6 , SO 2 OH, SO 2 OR 6 , SO 2 NH 2 , SO 2 NHR 6 , SO 2 NR 6 R 7 , alkyl, cycloalkyl, cycloheteroalkyl, aryl, or heteroaryl, with the proviso that at least one of R 1 , R 2 , R 3 , and R 4 is other than H; or R 1 and R 2 , R 2 and R 3 , or R 3 and R 4 , may together form part of a fused or unfused saturated or unsaturated ring system, optionally containing up to two heteroatoms selected from N, O, and S; R 5 is OH, OR 9 , CN, CONH 2 , CONHNH 2 , CONHOH, CONHR 9 , CONR 9 R 10 , NH 2 , NHR 9 , or NR 9 R 10 ; each R 6 , R 7 and R 8 is independently hydrocarbyl, or two of R 6 , R 7 and R 8 together form part of a saturated or unsaturated ring system, optionally containing up to two heteroatoms selected from N, O, and S; each R 9 and R 10 is independently hydrocarbyl, or R 9 and R 10 together form part of a saturated or unsaturated ring system, optionally containing up to two heteroatoms selected from N, O, and S; in the preparation of a medicament for treating a proliferative disorder.