1-BOC-5-溴-3-碘吲哚 | 850349-72-3

• 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: 1-BOC-5-溴-3-碘吲哚
• 中文别名: 1-叔丁氧羰基-5-溴-3-碘吲哚；1-Boc-5-溴-3-碘吲哚；5-溴-3-碘吲哚-1-羧酸叔丁酯
• 英文名称: tert-butyl 5-bromo-3-iodo-1H-indole-1-carboxylate
• 英文别名: tert-butyl 5-bromo-3-iodoindole-1-carboxylate
• CAS: 850349-72-3
• 化学式: C₁₃H₁₃BrINO₂
• 分子量: 422.06
• InChiKey: MCFJOLCLHJYCDS-UHFFFAOYSA-N

物化性质

• 沸点：
  434.0±48.0 °C(Predicted)
• 密度：
  1.81±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.6
• 重原子数：
  18
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.31
• 拓扑面积：
  31.2
• 氢给体数：
  0
• 氢受体数：
  2

安全信息

• 危险品标志：
  Xi
• 海关编码：
  2933990090
• 危险性防范说明：
  P261,P280,P301+P312,P302+P352,P305+P351+P338
• 危险性描述：
  H302,H315,H319,H335
• 储存条件：
  室温

SDS

Material Safety Data Sheet

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Section 1. Identification of the substance
Product Name: 1-Boc-5-bromo-3-iodo-indole
Synonyms: 5-Bromo-3-iodoindole-1-carboxylic acid tert-butyl ester

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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: 1-Boc-5-bromo-3-iodo-indole
CAS number: 850349-72-3

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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: C13H13BrINO2
Molecular weight: 422.1

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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, hydrogen Iodide.

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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：

  1-BOC-5-溴-3-碘吲哚 在 四(三苯基膦)钯 、 1,1'-双(二苯膦基)二茂铁二氯化钯(II)二氯甲烷复合物 sodium tungstate 、 copper(l) iodide 、 双氧水 、 potassium acetate 、 potassium carbonate 作用下， 以 1,4-二氧六环 、 水 、 溶剂黄146 、 N,N-二甲基甲酰胺 为溶剂， 反应 30.91h， 生成 tert-butyl 5-(5-(methylsulfonyl)-1,3,4-thiadiazol-2-yl)-3-(6-morpholinopyridin-2-yl)-1H-indole-1-carboxylate
  参考文献：
  名称：

  [EN] AZOLE COMPOUNDS AS PIM INHIBITORS
  [FR] COMPOSÉS D'AZOLE UTILISÉS EN TANT QU'INHIBITEURS DES PIM

  摘要：

  该发明涉及公式I和Ia的双环化合物及其盐。在某些实施例中，该发明涉及Pim-1和/或Pim-2和/或Pim-3蛋白激酶活性或酶功能的抑制剂或调节剂。在更进一步的实施例中，该发明涉及包含本文所披露的化合物的药物组合物，以及它们在预防和治疗Pim激酶相关疾病和病症，尤其是癌症中的用途。

  公开号：

  WO2012129338A1
• 作为产物：
  描述：

  5-溴吲哚 在 4-二甲氨基吡啶 、 三乙胺 、 potassium iodide 、 potassium hydroxide 作用下， 以 二氯甲烷 、 水 为溶剂， 反应 6.0h， 生成 1-BOC-5-溴-3-碘吲哚
  参考文献：
  名称：

  由2-（甲硫基）苯胺导向基团促进的N-甲基化氨基酸和肽的单选择性β-CH芳基化。

  摘要：

  2-（甲硫基）苯胺（MTA）指导的C（sp3）-H官能化是用于N-甲基化氨基酸的选择性β-修饰的有效而直接的方案。与8-氨基喹啉（AQ）导向基团相比，MTA的反应性降低，可实现高产率的选择性单芳基化，而不会形成副产物。该方案也适合于将高度官能化的侧链引入二肽的C-末端丙氨酸上。可以轻松除去MTA导向基团，从而提供游离羧酸作为有价值的组成部分。

  DOI：

  10.1039/c9ob00966c

文献信息

• Facile synthesis of isatins by direct oxidation of indoles and 3-iodoindoles using NIS/IBX
  作者：Ajeet Chandra、Navin R. Yadav、Jarugu Narasimha Moorthy

  DOI：10.1016/j.tet.2019.02.033

  日期：2019.4

  A facile one-pot access to a broad range of isatins by direct oxidation of indoles using NIS/IBX reagent in DMSO at 25 °C in very good isolated yields is reported. It is shown by mechanistic investigations that a number of substituted indoles react rapidly with NIS in DMSO to produce intermediary 3-iodoindoles, which undergo oxidation subsequently to isatins with IBX.

  据报道，使用NIS / IBX试剂在DMSO中于25°C进行吲哚直接氧化，可以很容易地一锅获得大量的Isatin，分离产率非常高。机理研究表明，许多取代的吲哚与DMSO中的NIS快速反应，生成中间体3-碘吲哚，随后被IBX氧化成靛红。
• Sequential Sonogashira and Suzuki Cross-Coupling Reactions in the Indole and Indazole Series
  作者：Bernhard Witulski、Sylvain Rault、Javier Azcon、Carole Alayrac、Anca Arnautu、Valérie Collot

  DOI：10.1055/s-2005-861825

  日期：——

  3-Iodoindoles, 5-bromo-3-iodoindoles and 5-bromo-3-iodoindazoles have been studied with respect to their reactivity and selectivity in palladium catalyzed Sonogashira and Suzuki cross-coupling reactions. As a result, sequential Sonogashira-Sonoga­shira, Sonogashira-Suzuki, and Suzuki-Sonogashira reactions with 5-bromo-3-iodoindoles or indazoles were used to obtain a large range of new functionalized indoles and indazoles, which are potential 5-HT receptor ligands.

  对3-碘吲哚、5-溴-3-碘吲哚和5-溴-3-碘吲唑的反应性和选择性进行了研究，尤其是在钯催化的Sonogashira和Suzuki交叉偶联反应中。因此，采用5-溴-3-碘吲哚或吲唑进行了顺序的Sonogashira-Sonogashira、Sonogashira-Suzuki和Suzuki-Sonogashira反应，以获得一系列新的功能化吲哚和吲唑，这些化合物是潜在的5-HT受体配体。
• Azole Compounds as PIM Inhibitors
  申请人：Wang Hui-Ling

  公开号：US20140187553A1

  公开（公告）日：2014-07-03

  The invention relates to bicyclic compounds of formulas I and Ia, and salts thereof. In some embodiments, the invention relates to inhibitors or modulators of Pim-1 and/or Pim-2, and/or Pim-3 protein kinase activity or enzyme function. In still further embodiments, the invention relates to pharmaceutical compositions comprising compounds disclosed herein, and their use in the prevention and treatment of Pim kinase related conditions and diseases, preferably cancer.

  本发明涉及式I和Ia及其盐的双环化合物。在某些实施例中，本发明涉及Pim-1和/或Pim-2以及/或Pim-3蛋白激酶活性或酶功能的抑制剂或调节剂。在更进一步的实施例中，本发明涉及包含本文所披露的化合物的制药组合物及其在预防和治疗Pim激酶相关疾病和条件，优选为癌症中的应用。
• Azole compounds as PIM inhibitors
  申请人：Wang Hui-Ling

  公开号：US09321756B2

  公开（公告）日：2016-04-26

  The invention relates to bicyclic compounds of formulas I and Ia, and salts thereof. In some embodiments, the invention relates to inhibitors or modulators of Pim-1 and/or Pim-2, and/or Pim-3 protein kinase activity or enzyme function. In still further embodiments, the invention relates to pharmaceutical compositions comprising compounds disclosed herein, and their use in the prevention and treatment of Pim kinase related conditions and diseases, preferably cancer.

  本发明涉及公式I和Ia的双环化合物及其盐。在某些实施例中，本发明涉及Pim-1和/或Pim-2和/或Pim-3蛋白激酶活性或酶功能的抑制剂或调节剂。在更进一步的实施例中，本发明涉及包含所述化合物的药物组合物，以及它们在预防和治疗Pim激酶相关疾病和疾病，尤其是癌症方面的应用。
• Linker-Based Pharmacophoric Design and Semisynthesis of Labdane Conjugates Active against Multi-Faceted Inflammatory Targets
  作者：Sangeetha Mohan、Lekshmy Krishnan、Nithya Madhusoodanan、Anjali Sobha、Renjitha Jalaja、Alaganandam Kumaran、Naveen Vankadari、Jayamurthy Purushothaman、Sasidhar B. Somappa

  DOI：10.1021/acs.jafc.3c09536

  日期：2024.3.27

  inflammatory mediators, viz., NO, TNF-α, IL-6, and IL-1α, in bacterial lipopolysaccharide-stimulated macrophages, as well as in-silico molecular modeling studies targeting the inflammation regulator COX-2 enzyme. Among the synthesized novel compounds, 5f exhibited the highest anti-inflammatory potential by inhibiting the COX-2 enzyme (IC50 = 17.67 ± 0.89 μM), with a 4-fold increased activity relative

  长期的炎症会导致多种炎症疾病的发生，如动脉粥样硬化、癌症、炎症性肠病、阿尔茨海默病等。炎症反应不受控制，其特点是促炎介质如一氧化氮（NO）、肿瘤坏死因子等过度释放。 -α (TNF-α)、白细胞介素-6 (IL-6)、白细胞介素-1α (IL-1α) 和炎症酶，例如环氧合酶-2 (COX-2)。因此，下调这些炎症介质是控制异常炎症和组织损伤的积极疗法。为了解决这个问题，本文中，我们通过芳香族/杂芳香族片段与拉丹烷二醛的基于战略连接子的分子杂交，提出了新型植物化学实体（NPCE）的合理设计和合成，拉丹烷二醛是从植物姜黄的药用和营养价值显着的根茎中分离出来的。 。为了验证其抗炎潜力，我们采用了一项全面的体外研究，评估其对细菌中 COX-2 酶和其他炎症介质（即NO、TNF-α、IL-6 和 IL-1α）的抑制作用。脂多糖刺激的巨噬细胞，以及针对炎症调节剂 COX-2 酶的计算机分子模型研究。在合成的新化合物中，