1-苄基-1H-吡咯-2-羧酸 | 18159-22-3

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡咯
• 中文名称: 1-苄基-1H-吡咯-2-羧酸
• 中文别名: 1-苄基-1H-吡咯-2-甲酸
• 英文名称: 1-benzyl-1H-pyrrole-2-carboxylic acid
• 英文别名: 1-benzylpyrrole-2-carboxylic acid
• CAS: 18159-22-3
• 化学式: C₁₂H₁₁NO₂
• 分子量: 201.225
• InChiKey: OGGDCEFWAMGBOB-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  15
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.08
• 拓扑面积：
  42.2
• 氢给体数：
  1
• 氢受体数：
  2

安全信息

• 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

SDS

Material Safety Data Sheet

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Section 1. Identification of the substance
Product Name: 1-Benzylpyrrole-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: 1-Benzylpyrrole-2-carboxylic acid
CAS number: 18159-22-3

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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.
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: C12H11NO2
Molecular weight: 201.2

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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.

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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-苄基-1H-吡咯-2-羧酸 在 正丁基锂 、 叠氮磷酸二苯酯 、 三乙胺 作用下， 以 正己烷 、 二氯甲烷 为溶剂， 生成 Methanesulfonic acid (R)-3-(1-benzyl-1H-pyrrol-2-yl)-2-oxo-oxazolidin-5-ylmethyl ester
  参考文献：
  名称：

  Synthesis and biological evaluation of enantiomerically pure pyrrolyl-oxazolidinones as a new class of potent and selective monoamine oxidase type A inhibitors

  摘要：

  Due to the key role played by monoamine oxidases (MAOs) in the metabolism of neurotransmitters, MAO inhibitors (MAOIs) represent an useful tool for the treatment of several neurological diseases. Among selective MAOIs, MAO-A inhibitors (e.g. clorgyline) are used as antidepressant and antianxiety drugs and are claimed to protect neuronal cells against apoptosis, and selective MAO-B inhibitors (e.g. L-deprenyl) can be used in the treatment of Parkinson's disease either alone or in combination with L-DOPA. However, they engender covalent bonds with the active site of the enzyme and induce irreversible inhibition; moreover, they tend to lose their initial selectivity at high dosages or with repeated administrations. Phenyloxazolidinones belong to third-generation-MAOIs, characterized by a selective and reversible inhibition of the enzyme. Among these molecules, the most representative are toloxatone and befloxatone, two selective and reversible MAO-A inhibitors used in therapy as antidepressant drugs. Going on our searches on CNS potentially active compounds containing a pyrrole moiety we prepared 3-(1H-pyrrol-1-yl)-2-oxazolidinones (1) and isomeric 3-(1H-pyrrol-2-and -3-yl)-2-oxazolidinones (2 and 3) as anti-MAO agents. Such derivatives resulted selective and reversible MAO-A inhibitors. The most potent compound is (R)-5-methoxymethyl-3-(1H-pyrrol-1-yl)-2-oxazolidinone (1b), endowed with very high potency (K(iMAO-A) = 4.9 nM) and A-selectivity (A-selectivity = 10,200, about 116-fold greater than that of befloxatone).

  DOI：

  10.1016/s0014-827x(03)00016-8
• 作为产物：
  描述：

  2-吡咯甲酸甲酯 在 水 、 sodium hydride 、 potassium hydroxide 作用下， 以 甲醇 、 N,N-二甲基甲酰胺 为溶剂， 反应 5.0h， 生成 1-苄基-1H-吡咯-2-羧酸
  参考文献：
  名称：

  非肽模拟物的设计和合成，该模拟物将免疫敏化髓鞘碱性蛋白（MBP83-96）表位定位为T细胞受体拮抗剂。

  摘要：

  致脑炎的T细胞与多发性硬化症（MS）的发病机理密切相关，多发性硬化症是中枢神经系统的一种自身免疫性脱髓鞘疾病。它们的刺激是由人白细胞抗原（HLA），免疫显性髓鞘碱性蛋白（MBP）表位和T细胞受体（TCR）之间的三分子复合物的形成触发的。我们在此详细介绍基于基于TCR与HLA结合识别的免疫优势MBP83-96表位的合理设计和合成非肽模拟分子的研究。我们将注意力集中在抑制三分子复合物的形成，从而抑制活化的T细胞的增殖。考虑到TCR和HLA-MBP83-96复合物之间的相互作用，产生了基于结构的药效团模型。结果，基于通过ZINC数据库获得的先导化合物设计了新的候选分子。此外，半经验和密度泛函理论方法被用于预测所提出的非肽模拟物和TCR之间的结合能。我们合成了六种分子，这些分子将在体外进一步评估为TCR拮抗剂。类似物15和16能够在一定程度上抑制来自免疫小鼠的免疫显性MBP83-99肽对T细胞的刺

  DOI：

  10.3390/ijms18061215
• 作为试剂：
  描述：

  ethyl 1-benzyl-1H-pyrrole-2-carboxylate 、 氢氧化钾 、 水 、 盐酸 在 乙酸乙酯 、 Sodium sulfate-III 、 1-苄基-1H-吡咯-2-羧酸 作用下， 以 甲醇 为溶剂， 反应 16.0h， 以to give 1-benzyl-1H-pyrrole-2-carboxylic acid (Intermediate 2-17), which的产率得到1-苄基-1H-吡咯-2-羧酸
  参考文献：
  名称：

  PYRROLO AND PYRAZOLOPYRIMIDINES AS UBIQUITIN-SPECIFIC PROTEASE 7 INHIBITORS

  摘要：

  本发明涉及USP7抑制剂，可用于治疗癌症、神经退行性疾病、免疫障碍、炎症性疾病、心血管疾病、缺血性疾病、病毒感染和疾病以及细菌感染和疾病，其化学式为：其中m，n，X1，X2，R1-R5，R5′和R6在此中描述。

  公开号：

  US20160185785A1

文献信息

• SmI₂-Promoted Radical Addition Reactions with <i>N</i>-(2-Indolylacyl)oxazolidinones:  Synthesis of Bisindole Compounds
  作者：Karl B. Lindsay、Francesc Ferrando、Kasper L. Christensen、Jacob Overgaard、Tomàs Roca、M.-Lluïsa Bennasar、Troels Skrydstrup

  DOI：10.1021/jo070273d

  日期：2007.5.1

  major product isolated in yields from 55 to 59% represents an unsymmetrical dimer arising from 1,4-addition to the 2-indolecarboxylic acid derivative of a possible ketyl-type radical anion intermediate originating from the reduction of the exocyclic carbonyl group of the N-acyl oxazolidinone. The minor dimer, represented by a symmetrical diketone, was produced in yields ranging from 11 to 23%. Even in the

  在-78°C下用二碘化sa处理吲哚环的取代模式不同的N-苄基2-吲哚羧酸的N-酰基恶唑烷酮导致形成两个吲哚二聚体产物。分离出的主要产物的产率为55-59％，其代表不对称的二聚体，该不对称的二聚体是由于N的外环羰基还原引起的可能的酮基型自由基阴离子中间体的2-4-吲哚羧酸衍生物的加成而产生的。-酰基恶唑烷酮。以对称二酮为代表的次要二聚体的产率为11％至23％。即使存在α，β-不饱和酰胺，二聚化也是优选的途径，而不是γ-酮酰胺的形成。用酸处理后，不对称的吲哚二聚体环化形成二吲哚醌。最后，在两种情况下，吡咯-2-羧酸和3-吲哚羧酸的N-酰基恶唑烷酮优选在SmI 2的存在下与丙烯酰胺进行CC键形成而不是二聚化。
• Catalyst-Controlled Chemodivergent Reactions of 2-Pyrrolyl-α-diazo-β-ketoesters and Enol Ethers: Synthesis of 1,2-Dihydrofuran Acetals and Highly Substituted Indoles
  作者：Gabriel Guerra Faura、Tena Nguyen、Stefan France

  DOI：10.1021/acs.joc.1c00826

  日期：2021.8.6

  chemodivergent reaction of pyrrolyl-α-diazo-β-ketoesters with enol ethers is reported. While Cu(II) catalysts selectively promoted a [3 + 2] cycloaddition to provide pyrrolyl-substituted 2,3-dihydrofuran (DHF) acetals, dimeric Rh(II) catalysts afforded 6-hydroxyindole-7-carboxylates via an unreported [4 + 2] benzannulation. The choice of enol ether proved to be crucial in determining both regioselectivity

  报道了吡咯基-α-重氮-β-酮酯与烯醇醚的催化剂控制的化学发散反应。虽然 Cu(II) 催化剂选择性地促进 [3 + 2] 环加成以提供吡咯基取代的 2,3-二氢呋喃 (DHF) 缩醛，但二聚 Rh(II) 催化剂通过未报道的 [4 + 2]苯环化。事实证明，烯醇醚的选择对于确定相应产物的区域选择性和产率至关重要（Cu(II) 的产率高达 91%，Rh(II) 催化的产率高达 82%）。此外，在路易斯酸的存在下，DHF 缩醛被证明可以作为 7-羟基吲哚-6-羧酸酯（由 Rh 形成的吲哚的异构体）和高度取代的呋喃的前体。因此，从常见的吡咯基-α-重氮-β-酮酯，
• Discovery of 2-Indole-acylsulfonamide Myeloid Cell Leukemia 1 (Mcl-1) Inhibitors Using Fragment-Based Methods
  作者：Nicholas F. Pelz、Zhiguo Bian、Bin Zhao、Subrata Shaw、James C. Tarr、Johannes Belmar、Claire Gregg、DeMarco V. Camper、Craig M. Goodwin、Allison L. Arnold、John L. Sensintaffar、Anders Friberg、Olivia W. Rossanese、Taekyu Lee、Edward T. Olejniczak、Stephen W. Fesik

  DOI：10.1021/acs.jmedchem.5b01660

  日期：2016.3.10

  Myeloid cell leukemia-1 (Mcl-1) is a member of the Bcl-2 family of proteins responsible for the regulation of programmed cell death. Amplification of Mcl-1 is a common genetic aberration in human cancer whose overexpression contributes to the evasion of apoptosis and is one of the major resistance mechanisms for many chemotherapies. Mcl-1 mediates its effects primarily through interactions with pro-apoptotic

  髓样细胞白血病-1 (Mcl-1) 是 Bcl-2 蛋白家族的成员，负责调节程序性细胞死亡。 Mcl-1 扩增是人类癌症中常见的遗传畸变，其过度表达有助于逃避细胞凋亡，并且是许多化疗的主要耐药机制之一。 Mcl-1 主要通过与含有促凋亡 BH3 的蛋白质相互作用来介导其作用，这些蛋白质通过利用其结合槽中的四个疏水性口袋实现对靶标的高亲和力。在这里，我们描述了使用基于片段的方法和基于结构的设计发现 Mcl-1 抑制剂。这些新型抑制剂对 Mcl-1 表现出低纳摩尔级的结合亲和力，选择性比 Bcl-xL 高 >500 倍。先导 Mcl-1 抑制剂与 Mcl-1 复合时的 X 射线结构提供了有关这些小分子如何与靶标结合的详细信息，并被广泛用于指导化合物优化。
• Synthesis of 2-(N-benzylpyrrolyl)-benzimidazoles using polyphosphoric acid prompted cyclocondensation
  作者：Bereket Mochona、Laine Le、Madhavi Gangapuram、Nelly Mateeva、Tiffany Ardley、Kinfe K. Redda

  DOI：10.1002/jhet.480

  日期：2010.11

  Synthesis of a series of 2‐substituted benzimidazoles was carried out for screening anti‐inflammatory activities. 2‐(N‐benzylpyrrolyl)‐benzimidazoles 9a, 9b, 9c, 9d, 9e, 9f, 9g, 9h, 9i, 9j, 9k were synthesized from N‐benzyl‐2‐pyrrole carboxylic acids 8a, 8b, 8c, 8d and 4‐substituted‐1,2‐phenylenediamines by cyclocondensation utilizing polyphosphoric acid (PPA) as condensing agent. The N‐benzyl‐2‐pyrrole

  合成了一系列2-取代苯并咪唑以筛选抗炎活性。由N-苄基-2-吡咯羧酸8a 、 8b 、 8c 、 8d和2- ( N-苄基吡咯基)-苯并咪唑9a 、 9b 、 9c 、 9d 、 9e 、 9f 、 9g 、 9h 、9i、 9j 、 9k合成使用多磷酸（PPA）作为缩合剂通过环缩合得到4-取代-1,2-苯二胺。 N-苄基-2-吡咯羧酸是通过使用NaH/DMF和适当取代的苄基卤对2-吡咯羧酸酯进行N-苄基化的标准方法制备的，然后进行碱性水解。 J.杂环化​​学，（2010）。
• N-heteroaryl indole carboxamides and analogues thereof, for use as glcokinase activators in the treatment of diabetes
  申请人：Lau F. Jesper

  公开号：US20070027140A1

  公开（公告）日：2007-02-01

  This invention relates to compounds that are activators of glucokinase and thus may be useful for the management, treatment, control, or adjunct treatment of diseases, where increasing glucokinase activity is beneficial. The compounds are of the general formula (I) wherin A and B are further defined in the application.

  本发明涉及激活葡萄糖激酶的化合物，因此可能对增加葡萄糖激酶活性有益的疾病的管理、治疗、控制或辅助治疗具有用处。这些化合物的一般式为（I）其中A和B在申请中有进一步定义。