4-溴-1H-吡咯-2-羧酰胺 | 196106-96-4

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 中文名称: 4-溴-1H-吡咯-2-羧酰胺
• 英文名称: 4-bromo-1H-pyrrole-2-carboxamide
• CAS: 196106-96-4
• 化学式: C₅H₅BrN₂O
• mdl: MFCD11504939
• 分子量: 189.011
• InChiKey: ZDOSNCDGCSOFIE-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.6
• 重原子数：
  9
• 可旋转键数：
  1
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  58.9
• 氢给体数：
  2
• 氢受体数：
  1

安全信息

• 海关编码：
  2933990090

SDS

Material Safety Data Sheet

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Section 1. Identification of the substance
Product Name: 4-Bromo-1H-pyrrole-2-carboxamide
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: 4-Bromo-1H-pyrrole-2-carboxamide
CAS number: 196106-96-4

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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.
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: C5H5BrN2O
Molecular weight: 189.0

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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
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：

  4-溴-1H-吡咯-2-羧酰胺 在 氯化亚砜 作用下， 以 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 5.0h， 生成 4-bromo-1H-pyrrole-2-carbonyl chloride
  参考文献：
  名称：

  一种脂肪酰胺水解酶抑制剂及其制备方法

  摘要：

  本发明公开了一种脂肪酰胺水解酶抑制剂及其制备方法，其结构式为其中，X选自C；R1选自H；R2选自H；R3选自H。经过测试的化合物对于人和大鼠脂肪酰胺水解酶具有很好地抑制活性，其hFAAH IC50（nM）为28，rFAAH IC50（nM）为110。说明本发明的化合物可以作为脂肪酰胺水解酶抑制剂用于相关药物的制备的后续研发。

  公开号：

  CN108409727A
• 作为产物：
  描述：

  1-(4-溴-1H-吡咯-2-基)-2,2,2-三氯-1-乙酮 在 氨 作用下， 以 水 、 乙腈 为溶剂， 反应 24.0h， 以98%的产率得到4-溴-1H-吡咯-2-羧酰胺
  参考文献：
  名称：

  Microwave-Assisted Fluorination of 2-Acylpyrroles: Synthesis of Fluorohymenidin

  摘要：

  Treatment of mono- and nonbrominated 2-acylpyrroles with Selectfluor under microwave conditions leads to fluorination of the pyrrole ring in the 5-position. In particular, 2-trichloroacetylated pyrrole can be fluorinated. As an example, dihydrofluorohymenidin was synthesized and dehydrogenated to fluorohymenidin as the first fluorinated pyrrole-imidazole alkaloid. Introduction of the vinyl double bond was achieved by chlorination of the 2-aminoimidazole moiety, followed by dehydrochlorination at 100 degrees C in DMF.

  DOI：

  10.1021/ol2029993

文献信息

• Vanadate-dependent bromoperoxidases from Ascophyllum nodosum in the synthesis of brominated phenols and pyrroles
  作者：Diana Wischang、Madlen Radlow、Jens Hartung

  DOI：10.1039/c3dt51582f

  日期：——

  aqueous tert-butanol (pH 6.2) molecular bromine as reagent for electrophilic hydrocarbon bromination. Alternative compounds, such as tribromide and hypobromous acid are not sufficiently electrophilic for being directly involved in carbon–bromine bond formation. A decrease in electrophilicity from bromine via hypobromous acid to tribromide correlates in a frontier molecular orbital (FMO) analysis with

  来自褐藻Ascophyllum nodosum的溴过氧化物酶，缩写为V Br PO（An I）和V Br PO（An II），显示出41％的序列同源性，并且α-螺旋二级结构的百分比相差两倍。蛋白质单体组成V Br PO（An I）的同二聚体和V Br PO（An II）的六聚体。溴过氧化物酶II与过氧化氢和溴化物的结合强度比V Br PO（An一世）。在氧化催化中，溴过氧化物酶I和II类似地快速转移过氧化氢和溴化物，生成吗啉-4-乙磺酸（MES）缓冲的叔丁醇水溶液（pH 6.2）分子溴作为亲电烃溴化试剂。诸如三溴化物和次溴酸之类的替代化合物尚不具有足够的亲电子性，无法直接参与碳-溴键的形成。从溴到次溴酸从溴到三溴化物的亲电性下降在前沿分子轨道（FMO）分析中与烯烃的π型HOMO和σ* Br，X之间的较大能隙相关型LUMO的溴化试剂。通过这种方法，可以预测底物的反应性和在钒酸盐依赖性溴过氧化
• AMIDES AS PIM INHIBITORS
  申请人：AMGEN INC.

  公开号：US20150329538A1

  公开（公告）日：2015-11-19

  The invention relates to amide-containing compounds of formula (1), 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（1）的含酰胺化合物及其盐。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与Pim激酶相关的疾病和病症，尤其是癌症方面的用途。
• Amides as pim inhibitors
  申请人：AMGEN INC.

  公开号：US09394297B2

  公开（公告）日：2016-07-19

  The invention relates to amide-containing compounds of formula (1), 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（1）的含酰胺化合物及其盐。在某些实施方式中，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。在更进一步的实施方式中，本发明涉及包含所披露的化合物的制药组合物，以及它们在预防和治疗Pim激酶相关疾病和病症，尤其是癌症方面的用途。
• Parameters for bromination of pyrroles in bromoperoxidase-catalyzed oxidations
  作者：Diana Wischang、Jens Hartung

  DOI：10.1016/j.tet.2011.04.010

  日期：2011.6

  Ester-, cyano-, and carboxamide-substituted 1H-pyrroles undergo electrophilic aromatic bromination, if treated with hydrogen peroxide and sodium bromide at pH 6.2 and 20 degrees C. Oxidation of bromide under such conditions is catalyzed by a vanadate(V)-dependent bromoperoxidase, in a substrate/enzyme ratio of 32-63 mu mol %. To obtain maximum yields of bromopyrroles (up to 91%) by spending least amount of substrates and catalyst, hydrogen peroxide and sodium bromide have to be added continuously to the enzyme and the 2-acceptor-substituted pyrrole (1.5 mmol) in a solution of morpholine-4-ethanesulfonic acid buffer. This technique was applied to prepare two marine natural products under biomimetic conditions, that is, methyl 4,5-dibromopyrrole-2-carboxylate (from Agelas oroides) and 4,5-dibromopyrrole-2-carboxamide (from Acanthella carteri). (C) 2011 Elsevier Ltd. All rights reserved.
• 一种脂肪酰胺水解酶抑制剂及其制备方法
  申请人：巨德峰

  公开号：CN108409727A

  公开（公告）日：2018-08-17

  本发明公开了一种脂肪酰胺水解酶抑制剂及其制备方法，其结构式为其中，X选自C；R1选自H；R2选自H；R3选自H。经过测试的化合物对于人和大鼠脂肪酰胺水解酶具有很好地抑制活性，其hFAAH IC50（nM）为28，rFAAH IC50（nM）为110。说明本发明的化合物可以作为脂肪酰胺水解酶抑制剂用于相关药物的制备的后续研发。