4-氯-1H-吡咯-2-羧酸 | 27746-03-8

• 物质功能分类: 有机原料 - 羧酸类化合物及衍生物
• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡咯
• 中文名称: 4-氯-1H-吡咯-2-羧酸
• 中文别名: 4-氯吡咯-2-羧酸
• 英文名称: 4-chloro-1H-pyrrole-2-carboxylic acid
• 英文别名: 4-chloropyrrole-2-carboxylic acid；4-chloropyrrole-2-carboxylate；4-chloro-pyrrole-2-carboxylic acid；4-Chlor-pyrrolcarbonsaeure-2；4-Chlorpyrrol-2-carbonsaeure
• CAS: 27746-03-8
• 化学式: C₅H₄ClNO₂
• mdl: MFCD07343826
• 分子量: 145.545
• InChiKey: YOTWVAYGATYZPA-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.2
• 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：
  53.1
• 氢给体数：
  2
• 氢受体数：
  2

安全信息

• 海关编码：
  2933990090
• 危险性防范说明：
  P261,P264,P270,P271,P280,P301+P312,P302+P352,P304+P340,P305+P351+P338,P330,P332+P313,P337+P313,P362,P403+P233,P405,P501
• 危险性描述：
  H302,H315,H319,H335

SDS

Material Safety Data Sheet

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Section 1. Identification of the substance
Product Name: 4-Chloro-1h-pyrrole-2-carboxylic acid
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-Chloro-1h-pyrrole-2-carboxylic acid
CAS number: 27746-03-8

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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.
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: C5H4ClNO2
Molecular weight: 145.5

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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.

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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-氯-1H-吡咯-2-羧酸 在 sodium hydroxide 、 N-氯代丁二酰亚胺 、 水 、 碳酸氢钠 、 N,N'-二环己基碳二亚胺 作用下， 以 四氢呋喃 、 水 、 乙腈 为溶剂， 反应 32.5h， 生成 5-[(6,7-dichloro-1-oxo-1,2-dihydropyrrolo[1,2-a]pyrazin-4-yl)methyl]-2-fluorobenzoic acid
  参考文献：
  名称：

  WO2007/138355

  摘要：

  公开号：
• 作为产物：
  描述：

  2,2,2-三氯-1-(4-氯-1H-吡咯-2-基)乙酮 在 sodium hydroxide 、 水 作用下， 反应 0.5h， 以38 mg的产率得到4-氯-1H-吡咯-2-羧酸
  参考文献：
  名称：

  伞花草 中吡咯基多烯的生物合成

  摘要：

  使用带有标记前体的进食研究阐明了真菌Auxarthron umbrinum中吡咯基多烯rumbrin（1）的生物合成。来自[ 15 N]-脯氨酸，[ 13 C]-蛋氨酸和[ 13 C]-乙酸盐的稳定同位素的掺入证实，它们分别是吡咯部分，甲基和rumbrin主链的前体。用吡咯-2-羧酸酯进行的标记稀释实验证实，它是rumbrin生物合成的直接前体。3-和4-氯吡咯羧酸酯也被认为是多烯生产中的前体。

  DOI：

  10.1039/b813236d

文献信息

• [EN] DYNAMIN-1-LIKE PROTEIN INHIBITORS<br/>[FR] INHIBITEURS DE PROTÉINE DE TYPE DYNAMINE-1
  申请人：MITOBRIDGE INC

  公开号：WO2018200674A1

  公开（公告）日：2018-11-01

  This application is directed to inhibitors of dynamin-l-like protein (Drpl) represented by the following structural formula (I): and methods for their use, such as to treat one or more DRPl-related diseases.

  该申请涉及以下结构公式（I）表示的dynamin-l样蛋白（Drpl）的抑制剂：以及它们的使用方法，例如用于治疗一种或多种与DRPl相关的疾病。
• Synthesis of 3-Azabicyclo[3.2.0]heptane-Derived Building Blocks via [3+2] Cycloaddition
  作者：Anton A. Homon、Oleksandr V. Hryshchuk、Serhii Trofymchuk、Oleg Michurin、Yuliya Kuchkovska、Dmytro S. Radchenko、Oleksandr O. Grygorenko

  DOI：10.1002/ejoc.201800972

  日期：2018.11.1

  Synthesis of 3‐azabicyclo[3.2.0]heptane‐derived building blocks via [3+2]cycloaddition of cyclobutene‐1‐carboxylate and azomethine ylide is described. It is shown that the title bicyclic scaffold is a three‐dimensional template which is well‐compatible with lead‐oriented parallel synthesis.

  描述了通过环丁烯-1-羧酸酯和甲亚胺叶立德的[3 + 2]环加成反应合成3-氮杂双环[3.2.0]庚烷的结构单元。结果表明标题双环支架是一个三维模板，与基于铅的平行合成很好地兼容。
• Gatekeeping Ketosynthases Dictate Initiation of Assembly Line Biosynthesis of Pyrrolic Polyketides
  作者：Dongqi Yi、Atanu Acharya、James C. Gumbart、Will R. Gutekunst、Vinayak Agarwal

  DOI：10.1021/jacs.1c02371

  日期：2021.5.26

  Assembly line biosynthesis of polyketide natural products involves checkpoints where identities of thiotemplated intermediates are verified before polyketide extension reactions are allowed to proceed. Determining what these checkpoints are and how they operate is critical for reprogramming polyketide assembly lines. Here we demonstrate that ketosynthase (KS) domains can perform this gatekeeping role

  聚酮化合物天然产物的流水线生物合成涉及检查点，在允许进行聚酮化合物延伸反应之前验证硫模板化中间体的身份。确定这些检查点是什么以及它们如何运行对于重新编程聚酮化合物装配线至关重要。在这里，我们证明了酮合酶 (KS) 域可以执行此守门角色。通过比较扩展吡咯基和卤化吡咯基底物的聚酮合酶的底物特异性，我们发现需要区分这两种底物的 KS 域具有高选择性。我们还发现 KS 活性位点中的氨基酸残基促进了这种选择性，并且这些残基适合进行合理的工程改造。另一方面，不需要在其天然生理环境中做出选择性决定的 KS 域是底物混杂的。我们还提供证据表明，通过非天然载体蛋白将底物输送到聚酮合酶会伴随着生物合成效率的降低。
• Production of anticancer polyenes through precursor-directed biosynthesis
  作者：Benjamin R. Clark、Stephen O'Connor、Deirdre Fox、Jacques Leroy、Cormac D. Murphy

  DOI：10.1039/c1ob05667k

  日期：——

  The biosynthesis of the pyrrolyl moiety of the fungal metabolite rumbrin originates from pyrrole-2-carboxylic acid. In an effort to produce novel derivatives with enhanced biological activity a series of substituted pyrrole-2-carboxylates were synthesised and incubated with the producing organism, Auxarthron umbrinum. Several 4-halo-pyrrole-2-carboxylic acids were incorporated into the metabolite yielding three new derivatives: 3-fluoro-, 3-chloro- and 3-bromo-isorumbrin, which were generated in milligram quantities enabling cytotoxicity assays to be conducted. The 3-chloro- and 3-bromo-isorumbrins had improved activity against HeLa cells compared with rumbrin; 3-bromoisorumbrin also showed dramatically improved activity towards a lung cancer cell line (A549).

  真菌代谢物rumbrin的吡咯基部分的生物合成起源于吡咯-2-羧酸。为了生产具有增强生物活性的新品系，合成了一系列取代的吡咯-2-羧酸酯，并与生产宿主Auxarthron umbrinum进行培养。将几种4-卤吡咯-2-羧酸纳入代谢物中，得到了三个新衍生物：3-氟-、3-氯-和3-溴-异rumbrin，生成量在毫克范围，使细胞毒性实验得以进行。与rumbrin相比，3-氯-和3-溴-异rumbrin在HeLa细胞上显示出更好的活性；3-溴-异rumbrin对肺癌细胞系（A549）也显示出显著改善的活性。
• [EN] BRANIMYCIN DERIVATIVES AND THEIR USE FOR THE TREATMENT OF BACTERIAL INFECTIOUS DISEASES<br/>[FR] DÉRIVÉS DE LA BRANIMYCINE ET LEUR UTILISATION POUR TRAITER DES MALADIES INFECTIEUSES D'ORIGINE BACTÉRIENNE
  申请人：GALAPAGOS NV

  公开号：WO2015028095A1

  公开（公告）日：2015-03-05

  Compounds are disclosed that have a formula represented by Formula (I) wherein A, B, R1, R2 and R3 are as defined herein. Novel compounds of the invention may be prepared as a pharmaceutical composition, and may be useful in the treatment of infectious diseases, in particular bacterial infectious diseases. The compounds may be active against a specific enzyme in the bacterial DNA replicative process, DNA polymerase IIIE.

  揭示了一种具有由公式（I）表示的化合物，其中A、B、R1、R2和R3如本文所定义。本发明的新化合物可以制备为药物组合物，并且可能在治疗传染病方面有用，特别是细菌性传染病。这些化合物可能对细菌DNA复制过程中的特定酶DNA聚合酶IIIE具有活性。