2-氯-6-氨基苯并噻唑 | 2406-90-8

• 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-6-氨基苯并噻唑
• 中文别名: 6-氨基-2-氯苯并噻唑
• 英文名称: 2-chlorobenzothiazol-6-ylamine
• 英文别名: 2-chlorobenzo[d]thiazol-6-amine；6-amino-2-chlorobenzothiazole；2-Chlor-6-aminobenzothiazol；2-chlorobenzothiazole-6-amine；2-chloro-1,3-benzothiazol-6-amine
• CAS: 2406-90-8
• 化学式: C₇H₅ClN₂S
• mdl: MFCD08276901
• 分子量: 184.649
• InChiKey: YPTWPDOGEAHMOR-UHFFFAOYSA-N

物化性质

• 熔点：
  155-157 °C
• 沸点：
  337.3±15.0 °C(Predicted)
• 密度：
  1.532

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  11
• 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：
  67.2
• 氢给体数：
  1
• 氢受体数：
  3

安全信息

• 海关编码：
  2934999090
• 危险性防范说明：
  P261,P280,P305+P351+P338
• 危险性描述：
  H302,H315,H319,H332,H335
• 储存条件：
  室温和干燥环境中使用。

SDS

Material Safety Data Sheet

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Section 1. Identification of the substance
Product Name: 6-Amino-2-chlorobenzothiazole
Synonyms:

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Section 2. Hazards identification
Harmful by inhalation, in contact with skin, and if swallowed.

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Section 3. Composition/information on ingredients.
Ingredient name: 6-Amino-2-chlorobenzothiazole
CAS number: 2406-90-8

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Section 4. First aid measures
Skin contact: Immediately wash skin with copious amounts of water for at least 15 minutes while removing
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.
Ingestion: Wash out mouth with copious amounts of water for at least 15 minutes. Seek medical attention.

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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.
Store in closed vessels, refrigerated.
Storage:

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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
Appearance: Not specified
Boiling point: No data
No data
Melting point:
Flash point: No data
Density: No data
Molecular formula: C7H5ClN2S
Molecular weight: 184.6

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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, hydrogen chloride, 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

反应信息

• 作为反应物：
  描述：

  2-氯-6-氨基苯并噻唑 在 三乙酰氧基硼氢化钠 、 溶剂黄146 作用下， 以 二甲基亚砜 、 1,2-二氯乙烷 为溶剂， 反应 6.0h， 生成 2-cyano-6-butylaminobenzothiazole
  参考文献：
  名称：

  Luciferins

  摘要：

  揭示了新型荧光素、制备荧光素的方法以及其用途。

  公开号：

  US20080226557A1
• 作为产物：
  描述：

  2-氯苯并噻唑 在 硫酸 、 硝酸 、 溶剂黄146 、 锌 作用下， 以 四氢呋喃 、 甲醇 为溶剂， 反应 5.0h， 生成 2-氯-6-氨基苯并噻唑
  参考文献：
  名称：

  苯并噻唑衍生物作为有效的抗肿瘤剂的合成及生物学评价。

  摘要：

  基于2-甲基-4-硝基-2H-吡唑-3-羧酸[2-（环己烷羰基氨基）苯并噻唑-6-基]酰胺（1），该化合物对致瘤细胞系2,6-二氯-将N- [2-（环丙烷羰基氨基）苯并噻唑-6-基]苯甲酰胺（13b）设计并合成为不含硝基的生物稳定衍生物。高效衍生物13b对肿瘤生长表现出优异的体内抑制作用。

  DOI：

  10.1016/j.bmcl.2005.05.077

文献信息

• Site-specific immobilization of biomolecules by a biocompatible reaction between terminal cysteine and 2-cyanobenzothiazole
  作者：Ping Wang、Chong-Jing Zhang、Ganchao Chen、Zhenkun Na、Shao Q. Yao、Hongyan Sun

  DOI：10.1039/c3cc43566k

  日期：——

  We report herein a new site-specific microarray immobilization method based on a biocompatible reaction between terminal cysteine and 2-cyanobenzothiazole (CBT). This immobilization strategy has been successfully applied to anchor small molecules, peptides and proteins onto microarrays.

  我们在此报告了一种基于末端半胱氨酸与2-氰基苯并噻唑（CBT）之间的生物相容性反应的新的特定于位点的微阵列固定方法。这种固定策略已成功应用于将小分子，肽和蛋白质锚定到微阵列上。
• Aminoluciferins as Functional Bioluminogenic Substrates of Firefly Luciferase
  作者：Hideo Takakura、Ryosuke Kojima、Yasuteru Urano、Takuya Terai、Kenjiro Hanaoka、Tetsuo Nagano

  DOI：10.1002/asia.201000873

  日期：2011.7.4

  Herein, we describe a design concept for functional bioluminogenic substrates based on the aminoluciferin (AL) scaffold, together with a convenient, high‐yield method for synthesizing N‐alkylated ALs. We confirmed the usefulness of ALs as bioluminogenic substrates by synthesizing three probes. The first was a conjugate of AL with glutamate, Glu–AL. When Glu–AL, the first membrane‐impermeable bioluminogenic

  萤火虫荧光素酶因其极高的信噪比而被广泛用作研究基因表达，基因传递等方面的检测基因。一系列生物发光底物的可用性将大大扩展萤光素-萤光素酶系统的适用性。本文中，我们描述了基于氨基荧光素（AL）支架的功能性生物发光底物的设计概念，以及用于合成N烷基化AL的便捷，高产率的方法。我们通过合成三种探针证实了ALs作为生物发光底物的有用性。首先是AL与谷氨酸Glu–AL的结合物。当将Glu–AL（荧光素酶的第一个膜不可渗透的生物发光底物）应用于荧光素酶转染的细胞时，未观察到发光。也就是说，通过使用Glu–AL，我们可以区分细胞内事件和细胞外事件。第二种是Cy5-AL，由近红外（NIR）花青荧光染料Cy5和AL组成，并发出NIR光。当Cy5–AL与萤光素酶反应时，由于从AL到Cy5的生物发光共振能量转移（BRET），观察到了来自Cy5的发光。NIR发射波长将允许在生物发光体内成像中从更深的组织观察到信号。
• Rational drug design of benzothiazole-based derivatives as potent signal transducer and activator of transcription 3 (STAT3) signaling pathway inhibitors
  作者：Dingding Gao、Nan Jin、Yixian Fu、Yueyue Zhu、Yujie Wang、Ting Wang、Yuehong Chen、Mingming Zhang、Qiang Xiao、Min Huang、Yingxia Li

  DOI：10.1016/j.ejmech.2021.113333

  日期：2021.4

  The cumulative evidence supports STAT3, a transcriptional mediator of oncogenic signaling, as a therapeutic target in cancer. The development of STAT3 inhibitors remain an active area of research as no inhibitors have yet to be approved for cancer treatment. In a continuing effort to develop more potent STAT3 inhibitors based on our previously identified hit compound 16w, a series of benzothiazole

  累积的证据支持STAT3（一种致癌信号的转录介质）作为癌症的治疗靶标。STAT3抑制剂的开发仍然是一个活跃的研究领域，因为尚未批准任何抑制剂用于癌症治疗。在基于我们先前确定的命中化合物16w不断开发更有效的STAT3抑制剂的过程中，设计，合成和生物学评估了一系列在STAT3的SH2结构域具有独特结合模式的苯并噻唑衍生物。值得注意的是，化合物B19对IC 50表现出优异的针对IL-6 / STAT3信号通路的活性通过萤光素酶报告基因测定法测定的值低至0.067μM。此外，多种化合物显示出对MDA-MB-468和JAK2突变HEL细胞系有效的抗增殖活性。使用蛋白质印迹法的进一步生化研究表明，B19阻断了Tyr 705和Ser 727处STAT3的磷酸化，从而抑制了STAT3介导的c-MYC和MCL-1基因表达。同时，它在MDA-MB-468和HEL细胞系中诱导癌细胞G2 / M期阻滞和凋亡。最
• Novel luciferin derivatives
  申请人：Takakura Hideo

  公开号：US20070155806A1

  公开（公告）日：2007-07-05

  A compound represented by the following general formula (I) or a salt thereof: [wherein R 1 and R 2 represent hydrogen atom, a C 1-6 alkyl group, or a group represented by the following formula (A): [wherein X 1 and X 2 represent hydrogen atom, or a group represented as —N(R 3 )(R 4 ) (R 3 and R 4 represent hydrogen atom, a C 1-6 alkyl group, a C 1-6 alkylcarbonyl group, or a C 1-6 alkyloxycarbonyl group); and n represents an integer of 1 to 6 ], provided that R 1 and R 2 do not simultaneously represent hydrogen atom), which is a novel luciferin derivative that serves as a luciferase substrate.

  由以下一般式（I）表示的化合物或其盐：[其中R1和R2代表氢原子，C1-6烷基或由以下式（A）表示的基团：[其中X1和X2代表氢原子或表示为—N（R3）（R4）的基团（R3和R4代表氢原子，C1-6烷基，C1-6烷基羰基基团或C1-6烷氧羰基基团）；n表示1到6的整数]，但R1和R2不能同时表示氢原子），这是一种作为荧光素酶底物的新型荧光素衍生物。
• [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。