2-氨基苯并噻唑-6-甲酸 | 93-85-6

• 物质功能分类: 医药中间体 - 原料药中间体
• 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-氨基苯并噻唑-6-甲酸
• 中文别名: 2-氨基-6-苯并噻唑羧酸；2-氨基苯丙噻唑-6-羧酸；2-氨基苯并噻唑-6-羧酸
• 英文名称: 2-aminobenzothiazole-6-carboxylic acid
• 英文别名: 2-aminobenzo[d]thiazole-6-carboxylic acid；2-amino-1,3-benzothiazole-6-carboxylic acid；2-amino-6-carboxybenzothiazole
• CAS: 93-85-6
• 化学式: C₈H₆N₂O₂S
• mdl: MFCD00054180
• 分子量: 194.214
• InChiKey: ZEAKWWWXCZMODH-UHFFFAOYSA-N

物化性质

• 熔点：
  265 ºC (DEC.)
• 沸点：
  466.6±37.0 °C(Predicted)
• 密度：
  1.604

计算性质

• 辛醇/水分配系数(LogP)：
  1.8
• 重原子数：
  13
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  104
• 氢给体数：
  2
• 氢受体数：
  5

安全信息

• TSCA：
  Yes
• 危险等级：
  IRRITANT
• 危险品标志：
  Xi
• 海关编码：
  2934999090
• 危险性防范说明：
  P261,P305+P351+P338
• 危险性描述：
  H315,H319,H335
• 储存条件：
  存放于室温、密封且干燥的环境中。

SDS

Material Safety Data Sheet

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Section 1. Identification of the substance
2-Aminobenzothiazole-6-carboxylic acid
Product Name:
Synonyms:

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Section 2. Hazards identification
Harmful by inhalation, in contact with skin, and if swallowed.
H315: Causes skin irritation
H319: Causes serious eye irritation
H335: May cause respiratory irritation
P261: Avoid breathing dust/fume/gas/mist/vapours/spray
Wear protective gloves/protective clothing/eye protection/face protection
P280:
P305+P351+P338: IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses if present
and easy to do – continue rinsing
P304+P340: IF INHALED: Remove victim to fresh air and keep at rest in a position comfortable for breathing
P405: Store locked up

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Section 3. Composition/information on ingredients.
2-Aminobenzothiazole-6-carboxylic acid
Ingredient name:
CAS number: 93-85-6

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Section 4. First aid measures
Immediately wash skin with copious amounts of water for at least 15 minutes while removing
Skin contact:
contaminated clothing and shoes. If irritation persists, seek medical attention.
Eye contact: Immediately wash skin with copious amounts of water for at least 15 minutes. Assure adequate
flushing of the eyes by separating the eyelids with fingers. If irritation persists, seek medical
attention.
Inhalation: Remove to fresh air. In severe cases or if symptoms persist, seek medical attention.
Wash out mouth with copious amounts of water for at least 15 minutes. Seek medical attention.
Ingestion:

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Section 5. Fire fighting measures
In the event of a fire involving this material, alone or in combination with other materials, use dry
powder or carbon dioxide extinguishers. Protective clothing and self-contained breathing apparatus
should be worn.

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Section 6. Accidental release measures
Personal precautions: Wear suitable personal protective equipment which performs satisfactorily and meets local/state/national
standards.
Respiratory precaution: Wear approved mask/respirator
Hand precaution: Wear suitable gloves/gauntlets
Skin protection: Wear suitable protective clothing
Eye protection: Wear suitable eye protection
Methods for cleaning up: Mix with sand or similar inert absorbent material, sweep up and keep in a tightly closed container
for disposal. See section 12.
Environmental precautions: Do not allow material to enter drains or water courses.

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Section 7. Handling and storage
Handling: This product should be handled only by, or under the close supervision of, those properly qualified
in the handling and use of potentially hazardous chemicals, who should take into account the fire,
health and chemical hazard data given on this sheet.
Storage: Store in closed vessels, refrigerated.

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Section 8. Exposure Controls / Personal protection
Engineering Controls: Use only in a chemical fume hood.
Personal protective equipment: Wear laboratory clothing, chemical-resistant gloves and safety goggles.
General hydiene measures: Wash thoroughly after handling. Wash contaminated clothing before reuse.

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Section 9. Physical and chemical properties
Not specified
Appearance:
Boiling point: No data
Melting point: No data
Flash point: No data
Density: No data
Molecular formula: C8H6N2O2S
Molecular weight: 194.2

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Section 10. Stability and reactivity
Conditions to avoid: Heat, flames and sparks.
Materials to avoid: Oxidizing agents.
Possible hazardous combustion products: Carbon monoxide, nitrogen oxides, sulfur oxides.

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Section 11. Toxicological information
No data.

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Section 12. Ecological information
No data.

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Section 13. Disposal consideration
Arrange disposal as special waste, by licensed disposal company, in consultation with local waste
disposal authority, in accordance with national and regional regulations.

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Section 14. Transportation information
Non-harzardous for air and ground transportation.

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Section 15. Regulatory information
No chemicals in this material are subject to the reporting requirements of SARA Title III, Section
302, or have known CAS numbers that exceed the threshold reporting levels established by SARA
Title III, Section 313.

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SECTION 16 - ADDITIONAL INFORMATION
N/A

制备方法与用途

用途

2-氨基苯并噻唑-6-甲酸是一种杂环有机物，可用作有机中间体。

2-氨基苯并噻唑是一类具有多种生物活性的化合物。例如，在临床上用于治疗肌萎缩性脊髓侧索硬化症的利鲁唑即属于此类；夫仑替唑则具备抗病毒、驱肠虫及免疫抑制等作用；N-酰基取代的2-氨基苯并噻唑可以抑制HIV病毒；而N-芳基取代的2-氨基苯并噻唑展现出较强的抗癌活性。此外，2-氨基苯并噻唑还广泛应用于抗菌、抗病毒和抗炎等领域，并在治疗帕金森病及糖尿病等药物的研究中发挥重要作用。因此，在药物化学领域，2-氨基苯并噻唑占据着极其重要的地位。

制备 步骤1：4-氨基-3-硫氰基苯甲腈（3）

将10.0克（0.08摩尔）的化合物(2)、13.0克（0.17摩尔）的硫氰酸铵和100毫升冰醋酸加入到250毫升三颈瓶中。室温下缓慢滴加含有12.8克溴（0.08摩尔）、25毫升冰醋酸溶液，大约需要15分钟。完成后，在搅拌下反应3小时。反应完全后，用200毫升水萃取生成大量橙黄色固体，静置过夜后抽滤，并用少量水洗涤，晾干以获得产物(3)，产率为91.3%，熔点为168~170℃。

步骤2：2-氨基苯并噻唑-6-甲酸（4）

将13.0克（0.07摩尔）的化合物(3)、120毫升水和60毫升浓盐酸加入到另一250毫升三颈瓶中，于100℃左右回流搅拌反应10小时。待反应完全后静置，收集析出固体并用少量水洗涤，晾干以获得橙黄色固体产物。

反应信息

• 作为反应物：
  描述：

  2-氨基苯并噻唑-6-甲酸 在 盐酸 作用下， 生成 2-氨基苯并噻唑-6-羧酸乙酯
  参考文献：
  名称：

  Takahashi; Numata, Yakugaku Zasshi/Journal of the Pharmaceutical Society of Japan, 1946, vol. 66, p. Ausg. B, S. 75

  摘要：

  DOI：
• 作为产物：
  描述：

  2-氨基苯并噻唑-6-甲酸甲酯 在 sodium hydroxide 作用下， 以 乙醇 为溶剂， 反应 4.0h， 以33%的产率得到2-氨基苯并噻唑-6-甲酸
  参考文献：
  名称：

  Phenylimidazole derivatives as new inhibitors of bacterial enoyl-ACP reductase FabK

  摘要：

  Novel FabK inhibitors with antibacterial activity against Streptococcus pneuinoniae were synthesized and evaluated. Through SAR studies of our initial hit compound 2-(1H-benz[d]imidazol-2-ylthio)-N-(6-methoxycarbonylbenzo[d]thiazo1-2-yl)acetamide, a series of novel phenylimidazole derivatives were discovered as potent FabK inhibitors. (c) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2007.06.040
• 作为试剂：
  描述：

  对氨基苯甲酸 、 potassium thioacyanate 、 溴 在 盐酸 、 2-氨基苯并噻唑-6-甲酸 作用下， 以 溶剂黄146 、 水 为溶剂， 反应 16.25h， 生成 2-氨基苯并噻唑-6-甲酸
  参考文献：
  名称：

  Water-soluble polymer-based cantharimides as potentially selective anti-tumor agents

  摘要：

  一种鞣酸酐化合物可以包括公式（1）的骨架。R1、R2、R3和R4可以独立地从H、C（O）OR5、C（O）R6、C（O）NR7R8、NR9C（O）R10、N-R11R12、O-R13、S-R14、P（O）（OR15）（OR16）、As（O）（OR17）（OR18）、SO2R19、SO3R20和B（OR21）的群中选择。X1至X4可以独立地从氮和碳的群中选择，使得X1至X4不全为氢。Y1、Y2和R5至R21可以独立地从氢、C1-12-烷基、-芳基、杂芳基和生物活性聚合物的群中选择。

  公开号：

  US08344007B2

文献信息

• Inhibitors of cathepsin S
  申请人：IRM LLC

  公开号：US20040198780A1

  公开（公告）日：2004-10-07

  The present invention provides compounds, compositions and methods for the selective inhibition of cathepsin S. In a preferred aspect, cathepsin S is selectively inhibited in the presence of at least one other cathepsin isozyme (e.g., cathespin K). The present invention also provides methods for treating a disease state in a subject by selectively inhibiting cathepsin S.

  本发明提供了用于选择性抑制蛋白酶S的化合物、组合物和方法。在一个优选方面，当至少存在另一种蛋白酶同工酶（例如，蛋白酶K）时，选择性地抑制蛋白酶S。本发明还提供了通过选择性抑制蛋白酶S来治疗受试者疾病状态的方法。
• An efficient one-pot synthesis of 2-aminobenzothiazoles from substituted anilines using benzyltrimethylammonium dichloroiodate and ammonium thiocyanate in DMSO:H2O
  作者：Reuben Dass、Matt A. Peterson

  DOI：10.1016/j.tetlet.2021.153388

  日期：2021.10

  and ammonium thiocyanate (1.0 equiv) in DMSO:H2O (9:1) at 70 °C gave the corresponding 2-aminobenzothiazoles in excellent isolated yields (75–97%; ave. yield for all substrates = 90%). The reaction worked well for 2(4)-mono-, 2,4-di-, or 3,4,5-tri-substituted anilines, and a wide range of both electron donating groups (MeO, HO, CF3O, Me) and electron withdrawing groups (NO2, CN, CO2Et, CO2H, Cl, F)

  在 DMSO:H 2 O (9:1) 中，在 70 °C 下用苄基三甲基二氯碘酸铵（1.2 当量）和硫氰酸铵（1.0 当量）处理各种取代苯胺，得到相应的 2-氨基苯并噻唑，分离产率高（75-97 %；所有底物的平均产率 = 90%）。该反应适用于 2(4)-单-、2,4-二-或 3,4,5-三-取代的苯胺，以及范围广泛的两种给电子基团（MeO、H2O、CF 3 O、 Me）和吸电子基团（NO 2、CN、CO 2 Et、CO 2 H、Cl、F）耐受性良好。这种方法为其他方法提供了一种有用的替代方法，这些方法要么效率较低（需要 3-7 倍当量的试剂），要么使用剧毒和腐蚀性液体溴2作为氧化剂。
• Small molecule inhibition of microRNA-21 expression reduces cell viability and microtumor formation
  作者：Nicholas Ankenbruck、Rohan Kumbhare、Yuta Naro、Meryl Thomas、Laura Gardner、Cole Emanuelson、Alexander Deiters

  DOI：10.1016/j.bmc.2019.05.044

  日期：2019.8

  one of the most established oncogenic miRNAs, is found to be upregulated in a wide range of cancers making it an attractive therapeutic target. Employment of a luciferase-based live-cell reporter assay in a high-throughput screen of >300,000 small molecules led to the discovery of a new class of ether-amide miR-21 inhibitors. Following a structure-activity relationship study, an optimized lead molecule

  MicroRNA（miRNA）是短的非编码RNA分子，估计可调节大量蛋白质编码基因的表达，并与多种生物学过程有关，例如发育，分化，增殖和细胞存活。miRNA的失调归因于各种人类疾病（包括癌症）的发作和发展。发现MicroRNA-21（miR-21）是最成熟的致癌miRNA之一，在多种癌症中均被上调，使其成为有吸引力的治疗靶标。在> 300,000个小分子的高通量筛选中使用基于荧光素酶的活细胞报告基因测定法，导致发现了一类新型的醚酰胺miR-21抑制剂。经过结构-活性关系研究，发现优化的前导分子可抑制miR-21转录。此外，该抑制剂通过诱导凋亡在宫颈癌细胞系中显示出细胞毒性，并且在长期的克隆形成测定中能够减少微肿瘤的形成。总而言之，这项工作报告了一种新的miR-21小分子抑制剂的发现，并证明了其作为癌症治疗替代方法的潜力。
• Salt of 6-carboxy-3-methylbenzothiazolone hydrazone hydrate in
  申请人：ActiMed Laboratories, Inc.

  公开号：US05710012A1

  公开（公告）日：1998-01-20

  Water soluble salts of hydrazone compounds react quickly with aniline compounds in the presence of a peroxidase and hydrogen peroxide to provide a color which can be measured spectrophotometrically or visually, either in solution or when incorporated in a device for the measurement of analytes of interest. These water-soluble hydrazone salts are useful in determining hydrogen peroxide or an analyte which reacts to produce hydrogen peroxide in an aqueous liquid, by, in the presence of a substance having peroxidative activity, physically contacting a sample of a liquid with a dye-forming composition comprising a water-soluble salt of a hydrazone compound and a substituted or unsubstituted aniline compound to produce a colored dye; and detecting the dye formed as a result of the presence of hydrogen peroxide or an analyte which reacts to produce hydrogen peroxide.

  水溶性腙化合物的盐在过氧化物酶和过氧化氢存在下与苯胺化合物迅速反应，产生一种颜色，可以通过分光光度法或目视法测量，无论是在溶液中还是在用于测量感兴趣分析物的装置中。这些水溶性腙盐在确定水溶液中的过氧化氢或产生过氧化氢的分析物方面很有用，方法是在存在具有过氧化活性的物质的情况下，将液体样品与包含水溶性腙化合物盐和取代或未取代苯胺化合物的染料形成组合物物理接触，产生一种有色染料；并检测由于存在过氧化氢或产生过氧化氢的分析物而形成的染料。
• WATER-SOLUBLE POLYMER-BASED CANTHARIMIDES AS POTENTIALLY SELECTIVE ANTI-TUMOR AGENTS
  申请人：Tang Johnny Cheuk-on

  公开号：US20100273840A1

  公开（公告）日：2010-10-28

  A cantharimide compound may include the backbone of formula (1). R 1 , R 2 , R 3 , and R 4 may be independently selected from the group consisting of H, C(O)OR 5 , C(O)R 6 , C(O)NR 7 R 8 , NR 9 C(O)R 10 , N—R 11 R 12 , O—R 13 , S—R 14 , P(O)(OR 15 )(OR 16 ), As(O)(OR 17 )(OR 18 ), SO 2 R 19 , SO 3 R 20 , and B(OR 21 ). X 1 to X 4 may be independently selected from the group consisting of nitrogen and carbon, such that X 1 to X 4 are not all hydrogen. Y 1 , Y 2 and R 5 to R 21 may be independently selected from the group consisting of hydrogen, C 1-12 -alkyl, -aryl, heteroaryl, and a bioactive polymer.

  一种鞣酰亚胺化合物可能包括式（1）的骨架。R1、R2、R3和R4可以独立地从H、C（O）OR5、C（O）R6、C（O）NR7R8、NR9C（O）R10、N—R11R12、O—R13、S—R14、P（O）（OR15）（OR16）、As（O）（OR17）（OR18）、SO2R19、SO3R20和B（OR21）的组中选择。X1到X4可以独立地从氮和碳的组中选择，使得X1到X4不全为氢。Y1、Y2和R5到R21可以独立地从氢、C1-12-烷基、芳基、杂芳基和生物活性聚合物的组中选择。