5-溴-7-硝基二氢吲哚 | 80166-90-1

• 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 - 吲哚及其衍生物
• 中文名称: 5-溴-7-硝基二氢吲哚
• 中文别名: 5-溴-7-硝基吲哚啉；5-溴-7-硝基-2,3-二氢-1H-吲哚
• 英文名称: 5-Bromo-7-nitroindoline
• 英文别名: 5-bromo-7-nitro-2,3-dihydro-1H-indole
• CAS: 80166-90-1
• 化学式: C₈H₇BrN₂O₂
• 分子量: 243.06
• InChiKey: VXKXMHDXFLFIFI-UHFFFAOYSA-N

物化性质

• 熔点：
  133-136°C
• 沸点：
  344.2±42.0 °C(Predicted)
• 密度：
  1.704±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  13
• 可旋转键数：
  0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  57.8
• 氢给体数：
  1
• 氢受体数：
  3

安全信息

• 危险等级：
  IRRITANT
• 危险等级：
  6.1
• 危险品标志：
  Xn,Xi
• 危险类别码：
  R20/21/22,R36/37/38
• 危险品运输编号：
  UN 2811
• 海关编码：
  2933990090
• 包装等级：
  III
• 安全说明：
  S26,S36/37/39
• 危险类别：
  6.1
• 危险性防范说明：
  P261,P280,P305+P351+P338,P311
• 危险性描述：
  H302+H312,H315,H319,H331,H335
• 储存条件：
  2-8°C

SDS

Material Safety Data Sheet

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Section 1. Identification of the substance
Product Name: 5-Bromo-7-nitroindoline
Synonyms:

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Section 2. Hazards identification
Harmful by inhalation, in contact with skin, and if swallowed.
H331: Toxic if inhaled
H302: Harmful if swallowed
H312: Harmful in contact with skin
Causes skin irritation
H315:
H319: Causes serious eye irritation
H335: May cause respiratory irritation
P261: Avoid breathing dust/fume/gas/mist/vapours/spray
P280: Wear protective gloves/protective clothing/eye protection/face protection
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.
Ingredient name: 5-Bromo-7-nitroindoline
CAS number: 80166-90-1

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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.
Immediately wash skin with copious amounts of water for at least 15 minutes. Assure adequate
Eye contact:
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.
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: C8H7BrN2O2
Molecular weight: 243.1

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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 bromide.

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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
UN Number: UN2811 Class: 6.1 Packing group: III
Proper shipping name: TOXIC SOLIDS, ORGANIC, N.O.S. (5-Bromo-7-nitroindoline)

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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

性状

淡黄色晶体

制备

关于吲哚类化合物的合成研究与方法改进不断见诸报道。根据文献报道，主要有Fischer合成法、L-B合成法、Reissert法以及“吲哚-吲哚啉-吲哚”等方法。其中，Fischer合成法适于合成吡咯环取代的吲哚衍生物；L-B合成法则适用于合成苯环取代的吲哚衍生物；Reissert法是合成2位取代吲哚的首选方法；而“吲哚-吲哚啉-吲哚”的步骤则能简便且温和地制备5位取代的吲哚化合物。本文以吲哚为原料，采用“吲哚-吲哚啉-吲哚”这一步骤合成了5-溴-7-硝基吲哚啉。其合成反应式如图1所示：


实验操作

将5-溴-7-硝基吲哚、水和三氯化铝加入到反应器中，加热回流，并分批加入锌粉。进行回流搅拌反应，用薄层色谱监测反应（展开剂：V(石油醚)：V(乙酸乙酯)=4:1，青岛海洋薄层层析硅胶板）。5小时后反应完全，过滤去除过量的锌粉，滤液用氢氧化钠溶液调pH至8，再用乙醚提取3次。醚层依次用水和饱和食盐水洗涤，无水硫酸钠干燥后过滤，蒸馏得淡黄色晶体5-溴-7-硝基吲哚啉。

反应信息

• 作为反应物：
  描述：

  5-溴-7-硝基二氢吲哚 在 吡啶 、 偶氮二异丁腈 、 三正丁基氢锡 、 铁粉 、 氯化铵 、 caesium carbonate 作用下， 以 水 、 异丙醇 、 甲苯 、 乙腈 为溶剂， 反应 51.0h， 生成 N-[1-(4-methoxybenzenesulfonyl)-2,3-dihydro-1H-indol-7-yl]isonicotinamide
  参考文献：
  名称：

  Indoline-sulfonamides compounds

  摘要：

  公开了一系列吲哚啉-磺酰胺化合物。吲哚啉-磺酰胺化合物的公式如公式（I）所示。在公式（I）中，R1是H或卤素；R2是Ar，Ar—C(O)—，Ar—CH2—，Ar—SO2—，Ar—O—C(O)，或R″—C(O)—，其中Ar是取代或未取代的C5-C20芳基、环烷基、杂环基或杂芳基，R′和R″独立地是C1-C10烷基或C1-C10烷氧基；R3是C5-C15芳基或C1-C10烷基。本发明公开的吲哚啉-磺酰胺化合物具有抑制微管蛋白聚合的特性，并可与适当的药学上可接受的载体一起用于治疗癌症和其他与微管蛋白聚合相关的疾病。

  公开号：

  US20080058386A1
• 作为产物：
  描述：

  N-已酰基-5-溴-7-硝基吲哚 在 sodium hydroxide 作用下， 以 四氢呋喃 、 甲醇 为溶剂， 反应 0.5h， 以3.89 g的产率得到5-溴-7-硝基二氢吲哚
  参考文献：
  名称：

  双吲哚取代基的位置和化学组成之间的关系决定了它们与 G-四链体 DNA 的相互作用。

  摘要：

  G-四链体 (G4) DNA 结构与基本生物过程和人类疾病有关，这引发了影响这些 DNA 结构的化合物的开发。然而，我们还需要更多关于小分子如何与 G4 DNA 结构相互作用的知识。本研究描述了新型双吲哚（3,3-二吲哚基甲基衍生物）的开发，并使用正交测定、生物物理技术和计算研究详细研究了它们如何与 G4 DNA 相互作用。这揭示了强烈结合并稳定 G4 DNA 结构的化合物，以及详细的结合相互作用，例如，表明电荷变化可以在 G4 DNA 结合中发挥关键作用。此外，所产生的结构-活性关系开启了在核心结构上替换或引入新取代基的可能性，这对于优化化合物特性或引入探针以进一步扩展这些化合物作为研究G4生物学的定制研究工具的可能性至关重要。

  DOI：

  10.1002/chem.202000579

文献信息

• Visible light mediated selective oxidation of alcohols and oxidative dehydrogenation of N-heterocycles using scalable and reusable La-doped NiWO₄ nanoparticles
  作者：R. Abinaya、K. Mani Rahulan、S. Srinath、Abdul Rahman、P. Divya、K. K. Balasubramaniam、R. Sridhar、B. Baskar

  DOI：10.1039/d1gc01729b

  日期：——

  A systematic study led to a selective synthesis of aldehydes under an argon atmosphere while the ODH of partially saturated heterocycles under an oxygen atmosphere resulted in very good to excellent yields. The methodology is atom economical and exhibits excellent tolerance towards various functional groups, and broad substrate scope. Furthermore, a one-pot procedure was developed for the sequential

  描述了在水性介质中使用可缩放和可重复使用的多相光氧化还原催化剂，可见光介导的各种伯/仲苯甲醇选择性和有效氧化为醛/酮和部分饱和杂环的氧化脱氢 (ODH)。一项系统研究导致在氩气氛下选择性合成醛，而在氧气氛下部分饱和杂环的 ODH 产生了非常好的收率。该方法是原子经济的，对各种官能团和广泛的底物范围表现出优异的耐受性。此外，开发了一种一锅法用于苯甲醇和杂芳基甲醇的顺序氧化，然后进行 Pictet-Spengler 环化，然后芳构化，以高分离产率获得 β-咔啉。发现该方法适用于放大和可重用性。据我们所知，这是在环境友好条件下使用可回收和多相光氧化还原催化剂氧化结构多样的芳基甲醇和部分饱和 N-杂环的 ODH 的第一份报告。
• Integrin expression inhibitors
  申请人：——

  公开号：US20040018192A1

  公开（公告）日：2004-01-29

  The present invention provides an integrin expression inhibitor, and an agent for treating arterial sclerosis, psoriasis, cancer, retinal angiogenesis, diabetic retinopathy or inflammatory diseases, an anticoagulant, or a cancer metastasis suppressor on the basis of an integrin inhibitory action. Namely, it provides an integrin expression inhibitor comprising, as an active ingredient, a sulfonamide compound represented by the following formula (I), a pharmacologically acceptable salt thereof or a hydrate of them. 1 In the formula, B means a C6-C10 aryl ring or 6- to 10-membered heteroaryl ring which may have a substituent and in which a part of the ring may be saturated; K means a single bond, —CH═CH— or —(CR 4b R 5b ) m b — (wherein R 4b and R 5b are the same as or different from each other and each means hydrogen atom or a C1-C4 alkyl group; and m b means an integer of 1 or 2); R 1 means hydrogen atom or a C1-C6 alkyl group; Z means a single bond or —CO—NH—; and R means a C6-C10 aryl ring or 6- to 10-membered heteroaryl ring which may have a substituent and in which a part of the ring may be saturated, respectively.

  本发明提供了一种整合素表达抑制剂，以及基于整合素抑制作用的用于治疗动脉硬化、银屑病、癌症、视网膜血管生成、糖尿病视网膜病变或炎症性疾病的药剂、抗凝剂或癌症转移抑制剂。即提供了一种包含以下式(I)所表示的磺胺化合物、其药理学上可接受的盐或其水合物作为活性成分的整合素表达抑制剂。 在该式中，B表示一个C6-C10芳基环或6-至10成员杂芳基环，可能具有取代基，并且环的一部分可能是饱和的；K表示一个单键，-CH═CH-或-(CR 4b R 5b ) m b -（其中R 4b 和R 5b 相同或不同，各自表示氢原子或C1-C4烷基；m b 表示1或2的整数）；R 1 表示氢原子或C1-C6烷基；Z表示一个单键或-CO-NH-；R表示一个C6-C10芳基环或6-至10成员杂芳基环，可能具有取代基，并且环的一部分可能是饱和的，分别。
• Reusable, homogeneous water soluble photoredox catalyzed oxidative dehydrogenation of N-heterocycles in a biphasic system: application to the synthesis of biologically active natural products
  作者：S. Srinath、R. Abinaya、Arun Prasanth、M. Mariappan、R. Sridhar、B. Baskar

  DOI：10.1039/d0gc00569j

  日期：——

  the substrate and catalyst at room temperature. Its potential applications to organic transformations are demonstrated by the synthesis of various biologically active N-heterocycles such as indoles, (iso)quinolines and β-carbolines and natural products such as eudistomin U, norharmane, and harmane and precursors to perlolyrine and flazin. Without isolation and purification, the catalyst solution can

  本文中，描述了一种在双相介质中使用可重复使用的均相钴-酞菁光氧化还原催化剂对四氢-β-咔啉，二氢吲哚和四氢-（异）喹啉进行氧化脱氢（ODH）的简单有效的方法。双相系统具有易于分离产物和均相光氧化还原催化剂有效重复使用的优点。而且，当前系统显着帮助克服了室温下底物和催化剂的溶解性问题。通过合成各种具有生物活性的N-杂环（如吲哚，（异）喹啉和β-咔啉）以及天然产物（如eudistomin U，降伤害药烷和harmane）以及全氟去氧灵和flazin的前体，证明了其在有机转化中的潜在应用。没有分离和纯化，催化剂溶液最多可重复使用5次，反应活性几乎相当。此外，以克为单位证明了反应的效率。据我们所知，这是有关在环境友好的条件下使用非贵重，可重复使用和均相的钴光氧化还原催化剂进行ODH反应的第一份报告。
• 1-Arylsulfonyl indoline-benzamides as a new antitubulin agents, with inhibition of histone deacetylase
  作者：Mei-Jung Lai、Ritu Ojha、Mei-Hsiang Lin、Yi-Min Liu、Hsueh-Yun Lee、Tony Eight Lin、Kai-Cheng Hsu、Chi-Yen Chang、Mei-Chuan Chen、Kunal Nepali、Jang-Yang Chang、Jing-Ping Liou

  DOI：10.1016/j.ejmech.2018.10.066

  日期：2019.1

  46 nM (KB-7D). Dual inhibitory potential of compound 9 was found as it demonstrated significant inhibitory potential against HDAC1, 2 and 6 in comparison to MS-275 (6). Some key interactions of 9 with the amino acid residues of the active site of tubulin and with amino acid residues of HDAC 1 isoform have been figured out by molecular modeling. Compound 9 also demonstrated significant in vivo efficacy in

  我们报告基于1-芳基磺酰基吲哚的苯甲酰胺的结构活性关系。苯甲酰胺（9）表现出显着的微管蛋白抑制作用，IC 50值为1.1μM，优于康培他汀A-4（3），并且对多种癌细胞具有显着的抗增殖活性，包括具有IC的MDR阳性细胞系50值分别为49 nM（KB），79 nM（A549），63 nM（MKN45），64 nM（KB-VIN10），43 nM（KB-S15）和46 nM（KB-7D）。化合物的双重抑制潜力9被发现，因为它显示出在比较针对HDAC1，2和6显著抑制潜力到MS-275（6）。9的一些关键交互通过分子建模已经找出了具有微管蛋白活性位点的氨基酸残基和具有HDAC 1同工型的氨基酸残基的化合物。化合物9在人非小细胞肺癌A549异种移植模型以及B细胞淋巴瘤BJAB异种移植肿瘤模型中也显示出显着的体内功效。
• 7-Aroyl-aminoindoline-1-sulfonamides as a Novel Class of Potent Antitubulin Agents
  作者：Jang-Yang Chang、Hsing-Pang Hsieh、Chi-Yen Chang、Kuo-Shun Hsu、Yi-Fang Chiang、Chi-Ming Chen、Ching-Chuan Kuo、Jing-Ping Liou

  DOI：10.1021/jm061076u

  日期：2006.11.1

  A novel series of 7-aroyl-aminoindoline-1-benzenesulfonamides showed excellent activity as inhibitors of tubulin polymerization through binding with the colchicine binding site of microtubules. Compound 15 and 16 display IC50 values of 1.1 and 1.2 microM, respectively. Compound 15 inhibited the human cancer cell growth of KB, MKN45, H460, HT29, and TSGH, as well as one human-resistant cancer line of

  一系列新型的7-芳酰基-氨基二氢吲哚-1-苯磺酰胺通过与微管的秋水仙碱结合位点结合，表现出优异的微管蛋白聚合抑制剂活性。化合物15和16的IC50值分别为1.1和1.2 microM。化合物15抑制人癌细胞KB，MKN45，H460，HT29和TSGH的生长以及一种人抗性KB-vin 10癌细胞系，IC50为9.6、8.8、9.4、8.6、10.8和分别为8.9 nM。