2-氯-5-硝基苯并噻唑 | 3622-38-6

• 物质功能分类: 有机原料 - 杂环化合物
• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并噻唑类
• 中文名称: 2-氯-5-硝基苯并噻唑
• 中文别名: 2-氯-5-硝基苯并噻唑(易制爆)
• 英文名称: 2-chloro-5-nitro-benzothiazole
• 英文别名: 2-chloro-5-nitro-1,3-benzothiazole；2-chloro-5-nitrobenzo[d]thiazole；2-chloro-5-nitrobenzothiazole；5-nitro-2-chlorobenzothiazole；2-Chlor-5-nitro-benzothiazol
• CAS: 3622-38-6
• 化学式: C₇H₃ClN₂O₂S
• 分子量: 214.632
• InChiKey: BSHJRTMGKFPQGZ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.4
• 重原子数：
  13
• 可旋转键数：
  0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  87
• 氢给体数：
  0
• 氢受体数：
  4

安全信息

• 危险性防范说明：
  P261,P280,P305+P351+P338
• 危险性描述：
  H302,H315,H319,H332,H335

反应信息

• 作为反应物：
  描述：

  2-氯-5-硝基苯并噻唑 在 palladium 10% on activated carbon 、 氢气 、 sodium carbonate 、 溶剂黄146 、 三氟乙酸 作用下， 以 甲醇 、 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 20.0h， 生成 5-amino-2-(4-(1-(1-(thiophen-2-ylmethyl)-1H-tetrazol-5-yl)propyl)piperazin-1-yl)benzothiazole
  参考文献：
  名称：

  Small molecules enhance functional O-mannosylation of Alpha-dystroglycan

  摘要：

  Alpha-dystroglycan (alpha-DG), a highly glycosylated receptor for extracellular matrix proteins, plays a critical role in many biological processes. Hypoglycosylation of alpha-DG results in various types of muscular dystrophies and is also highly associated with progression of majority of cancers. Currently, there are no effective treatments for those devastating diseases. Enhancing functional O-mannosyl glycans (FOG) of alpha-DG on the cell surfaces is a potential approach to address this unmet challenge. Based on the hypothesis that the cells can up-regulate FOG of alpha-DG in response to certain chemical stimuli, we developed a cell-based high-throughput screening (HTS) platform for searching chemical enhancers of FOG of alpha-DG from a large chemical library with 364,168 compounds. Sequential validation of the hits from a primary screening campaign and chemical works led to identification of a cluster of compounds that positively modulate FOG of alpha-DG on various cell surfaces including patient-derived myoblasts. These compounds enhance FOG of alpha-DG by almost ten folds, which provide us powerful tools for O-mannosylation studies and potential starting points for the development of drug to treat dystroglycanopathy. (c) 2015 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2015.11.011
• 作为产物：
  描述：

  2-氨基-5-硝基苯并噻唑 在 sodium hydroxide 、 氯化亚砜 作用下， 以 乙二醇 为溶剂， 生成 2-氯-5-硝基苯并噻唑
  参考文献：
  名称：

  Novel 2-aminobenzothiazoles as selective neuronal nitric oxide synthase inhibitors

  摘要：

  A series of substituted 2-aminobenzothiazole compounds have been synthesized and evaluated as nitric oxide synthase (NOS) inhibitors. Compound 14 shows activity in the nM range and is selective for the human neuronal NOS isoform. We have also evaluated the compounds against the rat NOS isoforms. For some of the compounds, there are significant differences in NOS inhibitory activities between the human and rat enzymes. For example, compound 10b has nM activity against the rat nNOS while low mu M activity against the human nNOS. (c) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2007.02.011

文献信息

• [EN] SUBSTITUTED BENZYLAMINE COMPOUNDS, THEIR USE IN MEDICINE, AND IN PARTICULAR THE TREATMENT OF HEPATITIS C VIRUS (HCV) INFECTION<br/>[FR] COMPOSÉS DE BENZYLAMINE SUBSTITUÉS, LEUR UTILISATION EN MÉDECINE, EN PARTICULIER DANS LE TRAITEMENT D'UNE INFECTION PAR LE VIRUS DE L'HÉPATITE C (VHC)
  申请人：ASTEX THERAPEUTICS LTD

  公开号：WO2013064538A1

  公开（公告）日：2013-05-10

  The invention provides compounds of the formula (I): or a salt, N-oxide or tautomer thereof, wherein A is CH, CF or nitrogen; E is CH, CF or nitrogen; and R0 is hydrogen or C1-2 alkyl; R1a is selected from CONH2; CO2H; an optionally substituted acyclic C1-8 hydrocarbon group; and an optionally substituted monocyclic carbocyclic or heterocyclic group of 3 to 7 ring members, of which 0, 1, 2, 3 or 4 are heteroatom ring members selected from O, N and S; R2 is selected from hydrogen and a group R2a; R2a is selected from an optionally substituted acyclic d-8 hydrocarbon group; an optionally substituted monocyclic carbocyclic or heterocyclic group of 3 to 7 ring members, of which 0, 1 or 2 ring members are heteroatom ring members selected from O, N and S; and an optionally substituted bicyclic heterocyclic group of 9 or 10 ring members, of which 1 or 2 ring members are nitrogen atoms; wherein at least one of R1 and R2 is other than hydrogen; R3 is an optionally substituted 3- to 10-membered monocyclic or bicyclic carbocyclic or heterocyclic ring containing 0, 1, 2 or 3 heteroatom ring members selected from N, O and S; R4a is selected from halogen; cyano; C1-4 alkyl optionally substituted with one or more fluorine atoms; C1-4 alkoxy optionally substituted with one or more fluorine atoms; hydroxy-C1-4 alkyl; and C1-2 alkoxy-C1-4 alkyl; R5 is selected from hydrogen and a substituent R5a; and R5a is selected from C1-2 alkyl optionally substituted with one or more fluorine atoms; C1-3 alkoxy optionally substituted with one or more fluorine atoms; halogen; cyclopropyl; cyano; and amino, The compounds have activity against hepatitis C virus and can be used in the prevention or treatment of hepatitis C viral infections.

  该发明提供了以下式（I）的化合物，或其盐、N-氧化物或互变异构体，其中A为CH、CF或氮；E为CH、CF或氮；R0为氢或C1-2烷基；R1a选自CONH2；CO2H；一个可选择取代的非环状C1-8碳氢化合物基团；以及一个可选择取代的含有3至7个环成员的单环碳环或杂环基团，其中0、1、2、3或4个是从O、N和S中选择的杂原子环成员；R2选自氢和一个基团R2a；R2a选自一个可选择取代的非环状d-8碳氢化合物基团；一个可选择取代的含有3至7个环成员的单环碳环或杂环基团，其中0、1或2个环成员是从O、N和S中选择的杂原子环成员；以及一个可选择取代的含有9或10个环成员的双环杂环基团，其中1或2个环成员是氮原子；其中R1和R2中至少一个不是氢；R3选自一个可选择取代的含有0、1、2或3个从N、O和S中选择的杂原子环成员的3至10个成员的单环或双环碳环或杂环环；R4a选自卤素；氰基；C1-4烷基，可选择取代一个或多个氟原子；C1-4烷氧基，可选择取代一个或多个氟原子；羟基-C1-4烷基；和C1-2烷氧基-C1-4烷基；R5选自氢和一个取代基R5a；R5a选自C1-2烷基，可选择取代一个或多个氟原子；C1-3烷氧基，可选择取代一个或多个氟原子；卤素；环丙基；氰基；和氨基。这些化合物对丙型肝炎病毒具有活性，并可用于预防或治疗丙型肝炎病毒感染。
• Photochemistry of 5-nitro-1,2-benzisothiazole derivatives: effects of substituents, solvents and excitation wavelength
  作者：Hiroharu Tanikawa、Kazuhiro Ishii、Shun Kubota、Shiki Yagai、Akihide Kitamura、Takashi Karatsu

  DOI：10.1016/j.tetlet.2008.03.104

  日期：2008.5

  (1, R = substituents) in solution, undergo photochemical isomerization to produce 2-R-5-nitro-1,2-benzothiazole derivatives. Here, generalizations and limitations by the substituent, solvent, and excitation wavelength for the photoisomerization reaction of 5-nitro-1,2-benzisothiazoles are reported.

  溶液中的3-R-5-硝基-1，2-苯并噻唑衍生物（1，R =取代基）经过光化学异构化生成2-R-5-硝基-1,2-苯并噻唑衍生物。在此，报道了5-硝基-1,2-苯并噻唑的光异构化反应的取代基，溶剂和激发波长的一般化和限制。
• Discovery of simplified benzazole fragments derived from the marine benzosceptrin B as necroptosis inhibitors involving the receptor interacting protein Kinase-1
  作者：Mohamed Benchekroun、Ludmila Ermolenko、Minh Quan Tran、Agathe Vagneux、Hristo Nedev、Claire Delehouzé、Mohamed Souab、Blandine Baratte、Béatrice Josselin、Bogdan I. Iorga、Sandrine Ruchaud、Stéphane Bach、Ali Al-Mourabit

  DOI：10.1016/j.ejmech.2020.112337

  日期：2020.9

  tools based on simplified natural metabolites to help deciphering the molecular mechanism of necroptosis, simplified benzazole fragments including 2-aminobenzimidazole and the 2-aminobenzothiazole analogs were prepared during the synthesis of the marine benzosceptrin B. Conpounds inhibiting the RIPK1 protein kinase were discovered. A library of 54 synthetic analogues were prepared and evaluated through

  为了开发基于简化的天然代谢产物的新化学工具以帮助破译坏死病的分子机制，在海洋苯并缩合受体B的合成过程中制备了包括2-氨基苯并咪唑和2-氨基苯并噻唑类似物的简化苯并唑片段。抑制RIPK1的化合物蛋白激酶被发现。制备了54种合成类似物的文库，并通过表型筛选评估了FADD蛋白缺陷的人Jurkat T细胞中由TNF-α诱导的坏死性细胞死亡。本文报道了一系列2-氨基苯并唑类化合物通过抑制RIPK1蛋白激酶对坏死性细胞死亡的设计，合成和生物学评估。
• [EN] INHIBITORS OF 11-BETA-HYDROXY STEROID DEHYDROGENASE TYPE 1 AND TYPE 2<br/>[FR] INHIBITEURS DE 11-BETA-HYDROXY STEROIDE DEHYDROGENASE DE TYPE 1 ET DE TYPE 2
  申请人：STERIX LTD

  公开号：WO2004037251A1

  公开（公告）日：2004-05-06

  There is provided a compound having Formula (I): wherein one of R1 and R2 is a group of the Formula (a), wherein R4 is selected from H and hydrocarbyl, R5 is a hydrocarbyl group and L is an optional linker group, or R1 and R2 together form a ring substituted with the group (Formula (a)) wherein R3 is H or a substituent, and wherein X is selected from S, O, NR6 and C(R7)(R8), wherein R6 is selected from H and hydrocarbyl groups, wherein each of R7 and R8 are independently selected from H and hydrocarbyl groups.

  提供一种具有化学式(I)的化合物：其中R1和R2中的一个是化学式(a)的基团，其中R4从H和烃基中选择，R5是烃基，L是可选的连接基团，或者R1和R2一起形成一个环，该环被基团(FORMULA (a))取代，其中R3是H或取代基，X从S、O、NR6和C(R7)(R8)中选择，其中R6从H和烃基中选择，R7和R8分别从H和烃基中独立选择。
• BENZOTHIAZOLE AND BENZOOXAZOLE DERIVATIVES AND METHODS OF USE
  申请人：Black Lawrence A.

  公开号：US20090163464A1

  公开（公告）日：2009-06-25

  Compounds of formula (I) are useful in treating conditions or disorders prevented by or ameliorated by histamine-3 receptor ligands. Also disclosed are pharmaceutical compositions of compounds of formula (I), methods for using such compounds and compositions, and a process for preparing the compounds.

  式(I)的化合物在治疗受组织胺-3受体配体预防或改善的症状或疾病方面具有用处。还公开了式(I)的化合物的药物组合物、使用这种化合物和组合物的方法，以及制备这些化合物的过程。