5-溴-3-氰基吲哚 | 90271-86-6

• 物质功能分类: 医药中间体 - 杂环化合物 - 吲哚类化合物
• 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-3-氰基吲哚
• 中文别名: 5-溴-3-吲哚甲腈；3-氰基-5-溴吲哚
• 英文名称: 5-bromo-1H-indole-3-carbonitrile
• 英文别名: 3-cyano-5-bromoindole；5-bromo-3-cyano-1H-indole；5-bromoindole-3-carbonitrile；5-Bromo-3-cyanoindole
• CAS: 90271-86-6
• 化学式: C₉H₅BrN₂
• mdl: MFCD04127133
• 分子量: 221.056
• InChiKey: ZPUQCVKBNRGSAP-UHFFFAOYSA-N

物化性质

• 沸点：
  405.9±25.0 °C(Predicted)
• 密度：
  1.74±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3
• 重原子数：
  12
• 可旋转键数：
  0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  39.6
• 氢给体数：
  1
• 氢受体数：
  1

安全信息

• 海关编码：
  2933990090
• 包装等级：
  III
• 危险类别：
  6.1
• 危险性防范说明：
  P264,P270,P301+P310+P330,P405,P501
• 危险品运输编号：
  2811
• 危险性描述：
  H301
• 储存条件：
  室温且干燥

SDS

Material Safety Data Sheet

---

Section 1. Identification of the substance
Product Name: 5-Bromo-3-cyanoindole
Synonyms:

---

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

---

Section 3. Composition/information on ingredients.
Ingredient name: 5-Bromo-3-cyanoindole
CAS number: 90271-86-6

---

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.

---

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.

---

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.

---

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:

---

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.

---

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: C9H5BrN2
Molecular weight: 221.1

---

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.

---

Section 11. Toxicological information
No data.

---

Section 12. Ecological information
No data.

---

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.

---

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

---

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.

---

SECTION 16 - ADDITIONAL INFORMATION
N/A

反应信息

• 作为反应物：
  描述：

  5-溴-3-氰基吲哚 在 降冰片烯 、 双(乙腈)氯化钯(II) 、 sodium hydride 、 potassium hydrogencarbonate 作用下， 以 N,N-二甲基乙酰胺 、 水 、 N,N-二甲基甲酰胺 为溶剂， 生成
  参考文献：
  名称：

  CREB结合蛋白溴结构域的高选择性抑制剂的基于结构的设计。

  摘要：

  临床前靶标验证需要化学探针，以探询新的生物学靶标和途径。需要CREB结合蛋白（CREBBP）/ EP300溴结构域的选择性抑制剂，以促进阐明与这些重要表观遗传学靶标相关的生物学。特别关注物化性质的药物化学优化为化学探针提供了理想的效价，选择性和渗透性属性。优化过程的重要特征是成功应用基于合理结构的药物设计来解决溴结构域选择性问题（尤其是针对与结构相关的BRD4蛋白）。

  DOI：

  10.1021/acs.jmedchem.6b01839
• 作为产物：
  描述：

  5-溴吲哚-3-甲醛 在 氨 、 氧气 作用下， 以 2-甲基-2-丁醇 为溶剂， 40.0 ℃ 、100.0 kPa 条件下， 反应 24.0h， 以89%的产率得到5-溴-3-氰基吲哚
  参考文献：
  名称：

  稳定且可重复使用的纳米级Fe 2 O 3催化好氧氧化工艺，用于选择性合成腈和伯酰胺

  摘要：

  在腈纶或酰胺基团形式的功能化分子中可持续引入氮基是至关重要的，因为在许多生命科学分子，天然产物和材料中都发现了含氮基序。因此，非常需要使用具有成本效益的催化剂和绿色试剂从容易获得的起始原料合成腈和酰胺的方法。就这一点而言，本文报道了在1 bar O 2的存在下，由醛和氨水进行的纳米级氧化铁催化的腈和伯酰胺的环境友好合成。或空气。在温和的反应条件下，该铁催化的需氧氧化过程继续进行，以合成功能化且结构多样的芳族，脂族和杂环腈。另外，应用该铁基方案，还已经在水介质中制备了伯酰胺。

  DOI：

  10.1039/c7gc02627g
• 作为试剂：
  描述：

  5-溴吲哚-3-甲醛 、 Azanium;azane;dihydrogen phosphate 、 硝基丙烷 在 水 、 5-溴-3-氰基吲哚 作用下， 以 溶剂黄146 为溶剂， 反应 16.0h， 以to afford 0.6 g (87%) of the desired nitrile的产率得到5-Bromo-7-methyl-1H-indole-3-carbonitrile
  参考文献：
  名称：

  SPIROCYCLIC ANTI-MIGRAINE COMPOUNDS

  摘要：

  本发明涉及公式（I）化合物作为降钙素基因相关肽受体（“CGRP受体”）拮抗剂，包括它们的药物组成物，识别它们的方法，使用它们的治疗方法以及它们在治疗神经原性血管扩张、神经原性炎症、偏头痛和其他头痛、热损伤、循环性休克、与绝经期潮红相关的面部潮红、气道炎症性疾病，如哮喘和慢性阻塞性肺疾病（COPD），以及其他可以通过拮抗CGRP受体来治疗的疾病的治疗中的应用。

  公开号：

  US20070149502A1

文献信息

• Compounds for the treatment of premature ejaculation
  申请人：——

  公开号：US20040063768A1

  公开（公告）日：2004-04-01

  The present invention relates to compounds of Formula (I) and pharmaceutically acceptable salts or solvates thereof and pharmaceutically acceptable formulations comprising said compounds 1 useful for the treatment of premature ejaculation, depression, attention deficit hyperactivity disorder, obsessive-compulsive disorder, post-traumatic stress disorder and substance abuse disorders.

  本发明涉及式(I)化合物及其药用可接受的盐或溶剂化物，以及包含所述化合物的药用可接受配方，用于治疗早泄、抑郁症、注意力缺陷/多动症、强迫症、创伤后应激障碍和物质滥用障碍。
• Dearomatization of 3-cyanoindoles by (3 + 2) cycloaddition: from batch to flow chemistry
  作者：Maxime Manneveau、Saori Tanii、Fanny Gens、Julien Legros、Isabelle Chataigner

  DOI：10.1039/d0ob00582g

  日期：——

  (3 + 2) Dearomatizing cycloaddition of 3-cyanoindoles occurs in smooth conditions with a non-stabilized azomethine ylide, to yield tricyclic indolines in only 1 min under microflow conditions using 3 equiv of the dipole precursor vs. 6 equiv. in a batch reactor.

  (3 + 2) 3-氰基吲哚与不稳定亚甲基亚胺叶立德发生去芳香化环加成反应，在微流条件下仅用1分钟，并且仅使用3倍当量的偶极前体，就能顺利生成三环吲哚啉，而在批量反应器中则需要6倍当量。

• 1,2,4‐Oxadiazole Topsentin Analogs with Antiproliferative Activity against Pancreatic Cancer Cells, Targeting GSK3β Kinase
  作者：Daniela Carbone、Barbara Parrino、Stella Cascioferro、Camilla Pecoraro、Elisa Giovannetti、Veronica Di Sarno、Simona Musella、Giulia Auriemma、Girolamo Cirrincione、Patrizia Diana

  DOI：10.1002/cmdc.202000752

  日期：2021.2.4

  series of topsentin analogs, in which the central imidazole ring of the natural lead was replaced by a 1,2,4‐oxadiazole moiety, was efficiently synthesized. All derivatives were pre‐screened for antiproliferative activity against the National Cancer Institute (NCI‐60) cell lines panel. The five most potent compounds were further investigated in various pancreatic ductal adenocarcinoma (PDAC) cell lines

  高效合成了一系列新的topsentin类似物，其中天然铅的中心咪唑环被1,2,4-恶二唑部分取代。所有衍生物均针对美国国家癌症研究所 (NCI-60) 细胞系面板的抗增殖活性进行了预筛选。在各种胰腺导管腺癌 (PDAC) 细胞系中进一步研究了五种最有效的化合物，包括 SUIT-2、Capan-1 和 Panc-1 细胞，引发 EC 50微摩尔和亚微摩尔范围内的值，与细胞迁移的显着减少有关。这些显着的结果可能是由于这些新的 topsentin 类似物对上皮-间质转化标志物的影响，包括 SNAIL-1/2 和金属蛋白酶-9。此外，Annexin V-FITC 和碘化丙啶染色后的流式细胞术分析表明，这些衍生物增强了 PDAC 细胞的凋亡。与这些数据保持一致，PathScan 细胞内信号传导和 ELISA 阵列显示 caspase-3 和 PARP 的裂解以及 GSK3β 磷酸化的显着抑制，表明该
• NOVEL CYCLIC BENZIMIDAZOLE DERIVATIVES USEFUL AS ANTI-DIABETIC AGENTS
  申请人：BOOKSER BRETT C.

  公开号：US20100081643A1

  公开（公告）日：2010-04-01

  Novel compounds of the structural formula (I) are activators of AMP-protein kinase and are useful in the treatment, prevention and suppression of diseases mediated by the AMPK-activated protein kinase. The compounds of the present invention are useful in the treatment of Type 2 diabetes, hyperglycemia, metabolic syndrome, obesity, hypercholesterolemia, and hypertension.

  结构式（I）的新化合物是AMP-蛋白激酶的激活剂，并且在治疗、预防和抑制由AMPK激活的蛋白激酶介导的疾病方面非常有用。本发明的化合物在治疗2型糖尿病、高血糖、代谢综合征、肥胖、高胆固醇血症和高血压方面非常有用。
• [EN] NOVEL CYCLIC BENZIMIDAZOLE DERIVATIVES USEFUL ANTI-DIABETIC AGENTS<br/>[FR] NOUVEAUX DÉRIVÉS DE BENZIMIDAZOLE CYCLIQUES UTILES COMME AGENTS ANTI-DIABÉTIQUES
  申请人：MERCK SHARP & DOHME

  公开号：WO2010047982A1

  公开（公告）日：2010-04-29

  Novel compounds of the structural formula (I) are activators of AMP-protein kinase and are useful in the treatment, prevention and suppression of diseases mediated by the AMPK-activated protein kinase. The compounds of the present invention are useful in the treatment of Type 2 diabetes, hyperglycemia, Metabolic Syndrome, obesity, hypercholesterolemia, and hypertension.

  结构式（I）的新化合物是AMP-蛋白激酶的激活剂，并且在治疗、预防和抑制由AMPK激活的蛋白激酶介导的疾病方面非常有用。本发明的化合物在治疗2型糖尿病、高血糖、代谢综合征、肥胖、高胆固醇血症和高血压方面非常有用。