2-氨基-4-溴-6-甲基苯并噻唑 | 76996-16-2

• 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-氨基-4-溴-6-甲基苯并噻唑
• 英文名称: 2-amino-4-bromo-6-methylbenzothiazole
• 英文别名: 4-bromo-6-methylbenzo[d]thiazol-2-amine；4-Bromo-6-methyl-1,3-benzothiazol-2-amine
• CAS: 76996-16-2
• 化学式: C₈H₇BrN₂S
• 分子量: 243.127
• InChiKey: PBKFYZMSNJCLOA-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  12
• 可旋转键数：
  0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  67.2
• 氢给体数：
  1
• 氢受体数：
  3

安全信息

• 海关编码：
  2934999090

反应信息

• 作为反应物：
  描述：

  2-氨基-4-溴-6-甲基苯并噻唑 在 盐酸 、 一水合肼 作用下， 反应 6.0h， 生成 5-bromo-3-hydroxy-7-methyl-1,2,4-triazolo-[3,4-b]-benzothiazole
  参考文献：
  名称：

  Novel Synthesis and Antimicrobial Activity of 3-Substituted 5-bromo-7-methyl-1,2,4-triazolo-[3,4-b]-benzothiazoles

  摘要：

  4‐Methyl acetanilide (1) on treatment with bromine in acetic acid, followed by hydrolysis with dilute HCl/NaOH solution, yielded 2‐bromo‐4‐methyl aniline (2), which on treatment with sodium thiocyanate in acetic acid afforded 2‐amino‐4‐bromo‐6‐methyl benzothiazole (3). Compound 3 in ethylene glycol was heated at 150°C with 80% hydrazine hydrate to get 4‐bromo‐2‐hydrazino‐6‐methyl benzothiazole (4). This hydrazino compound 4 on heating with formic acid for 3 h yielded 4‐bromo‐2‐hydrazinoformyl‐6‐methyl benzothiazole (5). Same compound 4 when heated independently with formic acid for 6 h/urea for 3 h/carbon disulfide in alkali afforded 5‐bromo‐7‐methyl (6)/5‐bromo‐3‐hydroxy‐7‐methyl (7)/5‐bromo‐3‐mercapto‐7‐methyl (8)‐1,2,4‐triazolo‐[3,4‐b]‐benzothiazoles, respectively. Compound 4 on heating with acetic acid/acetic anhydride gave acetyl benzothiazolyl derivative 9, which on cyclization with orthophosphoric acid yielded 5‐bromo‐3,7‐dimethyl‐1,2,4‐triazolo‐[3,4‐b]‐benzothiazole (10). All these newly synthesized compounds were screened for antimicrobial activity against Escherichia coli (Gram −ve), Bacillus subtilis (Gram +ve), Erwinia carotovora, and Xanthomonas citri using ampicillin, streptomycin, and penicillin as a standard for comparison.

  DOI：

  10.1002/jhet.885
• 作为产物：
  描述：

  4-甲基乙酰苯胺 在 盐酸 、 溴 、 sodium hydroxide 作用下， 以 水 、 溶剂黄146 为溶剂， 反应 1.0h， 生成 2-氨基-4-溴-6-甲基苯并噻唑
  参考文献：
  名称：

  Novel Synthesis and Antimicrobial Activity of 3-Substituted 5-bromo-7-methyl-1,2,4-triazolo-[3,4-b]-benzothiazoles

  摘要：

  4‐Methyl acetanilide (1) on treatment with bromine in acetic acid, followed by hydrolysis with dilute HCl/NaOH solution, yielded 2‐bromo‐4‐methyl aniline (2), which on treatment with sodium thiocyanate in acetic acid afforded 2‐amino‐4‐bromo‐6‐methyl benzothiazole (3). Compound 3 in ethylene glycol was heated at 150°C with 80% hydrazine hydrate to get 4‐bromo‐2‐hydrazino‐6‐methyl benzothiazole (4). This hydrazino compound 4 on heating with formic acid for 3 h yielded 4‐bromo‐2‐hydrazinoformyl‐6‐methyl benzothiazole (5). Same compound 4 when heated independently with formic acid for 6 h/urea for 3 h/carbon disulfide in alkali afforded 5‐bromo‐7‐methyl (6)/5‐bromo‐3‐hydroxy‐7‐methyl (7)/5‐bromo‐3‐mercapto‐7‐methyl (8)‐1,2,4‐triazolo‐[3,4‐b]‐benzothiazoles, respectively. Compound 4 on heating with acetic acid/acetic anhydride gave acetyl benzothiazolyl derivative 9, which on cyclization with orthophosphoric acid yielded 5‐bromo‐3,7‐dimethyl‐1,2,4‐triazolo‐[3,4‐b]‐benzothiazole (10). All these newly synthesized compounds were screened for antimicrobial activity against Escherichia coli (Gram −ve), Bacillus subtilis (Gram +ve), Erwinia carotovora, and Xanthomonas citri using ampicillin, streptomycin, and penicillin as a standard for comparison.

  DOI：

  10.1002/jhet.885

文献信息

• [EN] BICYCLIC HETEROARYL SUBSTITUTED COMPOUNDS<br/>[FR] COMPOSÉS BICYCLIQUES SUBSTITUÉS PAR HÉTÉROARYLE
  申请人：BRISTOL MYERS SQUIBB CO

  公开号：WO2018013774A1

  公开（公告）日：2018-01-18

  Disclosed are compounds of Formula (I) to (VIII): (I) (II) (III) (IV) (V) (VI) (VII) (VIII); or a stereoisomer, tautomer, pharmaceutically acceptable salt, solvate or prodrug thereof, wherein R3 is a bicyclic heteroaryl group substituted with zero to 3 R3a; and R1, R2, R3a, R4, and n are defined herein. Also disclosed are methods of using such compounds as PAR4 inhibitors, and pharmaceutical compositions comprising such compounds. These compounds are useful in inhibiting or preventing platelet aggregation, and are useful for the treatment of a thromboembolic disorder or the primary prophylaxis of a thromboembolic disorder.

  公开了公式(I)至(VIII)的化合物：(I) (II) (III) (IV) (V) (VI) (VII) (VIII)；或其立体异构体、互变异构体、药物可接受的盐、溶剂化物或前药，其中R3是与0至3个R3a取代的双环杂芳基团；且R1、R2、R3a、R4和n在此定义。还公开了使用这些化合物作为PAR4抑制剂的方法，以及包含这些化合物的药物组合物。这些化合物用于抑制或预防血小板聚集，用于治疗血栓栓塞障碍或作为血栓栓塞障碍的初级预防。
• HETEROARYL SUBSTITUTED PIPERIDINES
  申请人：Baumann Karlheinz

  公开号：US20110201605A1

  公开（公告）日：2011-08-18

  The invention relates to compounds of formula where hetaryl I, hetaryl II, R 1 , R 2 , R 3 , R 4 , m, n, and o are as defined in the specification or to pharmaceutically active acid addition salts thereof. The compounds of formula I are modulators for amyloid beta and thus may be useful for the treatment or prevention of a disease associated with the deposition of β-amyloid in the brain, in particular Alzheimer's disease, and other diseases such as cerebral amyloid angiopathy, hereditary cerebral hemorrhage with amyloidosis, Dutch-type (HCHWA-D), multi-infarct dementia, dementia pugilistica and Down syndrome.

  该发明涉及以下式的化合物 其中hetaryl I，hetaryl II， R 1 ， R 2 ， R 3 ，R 4 ，m，n和o如规范中所定义 或其药用活性酸盐。式I的化合物是淀粉样蛋白β的调节剂，因此可能对与大脑中β-淀粉样蛋白沉积相关的疾病的治疗或预防有用，特别是阿尔茨海默病，以及其他疾病，如脑淀粉样血管病，遗传性脑出血伴淀粉样变性，荷兰型（HCHWA-D），多梗塞性痴呆，拳击性痴呆和唐氏综合征。
• SUBSTITUTED BENZOAZOLE PDE4 INHIBITORS FOR TREATING PULMONARY AND CARDIOVASCULAR DISORDERS
  申请人：Singh Jasbir

  公开号：US20090130076A1

  公开（公告）日：2009-05-21

  The invention relates to substituted benzothiazoles, benzoxazoles—and their counterparts having pyridine and pyrimidine rings replacing the benzene ring—that are PDE4 inhibitors useful for treating stroke, myocardial infarct, and cardiovascular inflammatory conditions, to pharmaceutical compositions comprising these compounds, and to methods for the treatment of stroke, myocardial infarct, and cardiovascular inflammatory conditions in a mammal. The compounds have general formula I: in which A and B are carbocycles or heterocycles. A particular embodiment is

  这项发明涉及替代苯并噻唑、苯并噁唑以及它们的对应物，其中吡啶和嘧啶环取代苯环，这些化合物是PDE4抑制剂，用于治疗中风、心肌梗死和心血管炎症病症，以及包含这些化合物的药物组合物，以及在哺乳动物中治疗中风、心肌梗死和心血管炎症病症的方法。这些化合物具有一般式I：其中A和B是碳环或杂环。一个特定的实施例是
• Synthesis, Spectral Characterization and Biological Evaluation of New Substituted 2H-Pyrimido[2,1-b]benzothiazol-2-ones
  作者：Kshamta Goyal、Shikha Agarwal、Dinesh Agarwal、Naveen Gautam、D.C. Gautam

  DOI：10.2174/1570178614666161115163142

  日期：2017.1.3

  current years. The aim of this manuscript is to develop a one pot reaction for the synthesis of benzothiazole coupled pyrimidine compounds using alkynoic acids and substituted 2-aminobenzothiazoles under normal reaction conditions. Methods: Different 2-aminobenzothiazoles and substituted alkynoic acids have been used to synthesize 2H-Pyrimido[2,1-b]benzothiazol-2-ones via conjugate addition of the imino

  背景：在最近几年中，缩合嘧啶化合物因其巨大的生物学特性而备受关注。这些化合物引起了人们极大的兴趣，这在最近几年发表的大量评论和研究文章中得到了证明。该手稿的目的是开发一种在常规反应条件下使用炔酸和取代的2-氨基苯并噻唑合成一锅反应的方法，用于合成苯并噻唑偶联的嘧啶化合物。 方法：已使用不同的2-氨基苯并噻唑和取代的炔酸，通过将2-氨基苯并噻唑的亚氨基氮共轭加到炔酸的炔烃β-碳原子上来合成2H-嘧啶并[2,1-b]苯并噻唑-2-酮其次是闭环。根据元素分析和光谱数据（IR，1 H NMR，13 C NMR和质量）确定合成化合物的结构。评估合成的化合物的抗氧化剂（DPPH和ABTS分析）和抗菌活性（使用肉汤微量稀释法）。 结果：以中等至良好的产率（56-75％）获得了具有不同取代基的合成化合物。发现大多数化合物（6a，7a，8a）在DPPH和ABTS分析中具有更高的活性，并且还显示出显着的抗菌和抗真菌活性。
• Benzothiazole derivatives and methods of use
  申请人：Lucky, Ltd.

  公开号：US05380735A1

  公开（公告）日：1995-01-10

  The present invention relates to a novel benzothiazole derivative of the following general formula (I) or its (E) , (Z)isomer, and processes for preparation thereof, ##STR1## in which R.sup.1, R.sup.2 and R.sup.3 independently of one another represent hydrogen, halogen, straight and branched (C.sub.1 -C.sub.8)alkyl, (C.sub.1 -C.sub.8)halogenoalkyl or (C.sub.1 -C.sub.8)alkoxy, X represents N or CH, Y represents a group -OR.sup.4, SR.sup.5 or ##STR2## R.sup.4, R.sup.5, R.sup.6 and R.sup.7 independently of one another represent hydrogen, straight and branched (C.sub.1 -C.sub.16)alkyl, (C.sub.3 -C.sub.8)alkenyl, (C.sub.3 -C.sub.8)alkynyl, (C.sub.3 -C.sub.8)cycloalkyl, alkyl substituted with (C.sub.1 -C.sub.6)alkoxy or (C.sub.1 -C.sub.6)halogenoalkyl, or represent a substituted phenyl, phenylacyl or benzyl group wherein the possible substituent on the phenyl, phenylacyl or benzyl group includes halogen, straight and branched (C.sub.1 -C.sub.8)alkyl, (C.sub.1 -C.sub.8)alkoxy, (C.sub.3 -C.sub.8)alkenyl, (C.sub.3 -C.sub.8)alkynyl, phenoxy, nitro, cyano and a five- or six-membered heterocyclic group containing one to four nitrogen atoms. The compound of formula (I) is useful for combating phythopathogenic organisms and fungi present on animal.

  本发明涉及以下一般式（I）或其（E），（Z）异构体的新型苯并噻唑衍生物，以及其制备方法，其中R.sup.1，R.sup.2和R.sup.3彼此独立地代表氢，卤素，直链和支链（C.sub.1-C.sub.8）烷基，（C.sub.1-C.sub.8）卤代烷基或（C.sub.1-C.sub.8）氧烷基，X代表N或CH，Y代表-OR.sup.4，SR.sup.5或R.sup.4，R.sup.5，R.sup.6和R.sup.7彼此独立地代表氢，直链和支链（C.sub.1-C.sub.16）烷基，（C.sub.3-C.sub.8）烯基，（C.sub.3-C.sub.8）炔基，（C.sub.3-C.sub.8）环烷基，烷基取代（C.sub.1-C.sub.6）氧烷基或（C.sub.1-C.sub.6）卤代烷基，或代表取代苯基，苯基酰基或苄基团，其中苯基，苯基酰基或苄基团上的可能取代基包括卤素，直链和支链（C.sub.1-C.sub.8）烷基，（C.sub.1-C.sub.8）氧基，（C.sub.3-C.sub.8）烯基，（C.sub.3-C.sub.8）炔基，苯氧基，硝基，氰基和含有一到四个氮原子的五元或六元杂环基团。式（I）化合物对抗存在于动物上的植物病原体和真菌有用。