1-phenylbenzimidazole-5-carboxylic acid methyl ester | 220495-70-5

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并咪唑类
• 英文名称: 1-phenylbenzimidazole-5-carboxylic acid methyl ester
• 英文别名: methyl 1-phenylbenzimidazole-5-carboxylate；Methyl 1-phenyl-1H-benzo[d]imidazole-5-carboxylate
• CAS: 220495-70-5
• 化学式: C₁₅H₁₂N₂O₂
• 分子量: 252.272
• InChiKey: VATOEEFYHKVJSC-UHFFFAOYSA-N

物化性质

• 沸点：
  428.9±37.0 °C(Predicted)
• 密度：
  1.21±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3
• 重原子数：
  19
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.07
• 拓扑面积：
  44.1
• 氢给体数：
  0
• 氢受体数：
  3

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: Methyl 1-phenylbenzoimidazole-5-carboxylate
Synonyms: methyl 1-phenyl-1,3-benzodiazole-5-carboxylate

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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: Methyl 1-phenylbenzoimidazole-5-carboxylate
CAS number: 220495-70-5

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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: C15H12N2O2
Molecular weight: 252.3

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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-phenylbenzimidazole-5-carboxylic acid methyl ester 在 sodium hydroxide 作用下， 以 甲醇 为溶剂， 生成 1-Phenylbenzimidazole-5-carboxylic Acid Hydrochloride
  参考文献：
  名称：

  Benzimidazoles for inhibiting protein tyrosine kinase mediated cellular

  摘要：

  下面的I式苯并咪唑是蛋白酪氨酸激酶的抑制剂，对治疗细胞增殖很有用。这些化合物在治疗癌症、动脉粥样硬化、再狭窄和牛皮癣方面特别有效。

  公开号：

  US05990146A1
• 作为产物：
  描述：

  4-氯-3-硝基苯甲酸 在 palladium on activated charcoal N-甲基吗啉 、 盐酸 、 氢气 、 铜 作用下， 以 甲醇 、 异戊醇 、 乙二醇甲醚 、 乙酸乙酯 为溶剂， 反应 39.0h， 生成 1-phenylbenzimidazole-5-carboxylic acid methyl ester
  参考文献：
  名称：

  Structure−Activity Relationships for 1-Phenylbenzimidazoles as Selective ATP Site Inhibitors of the Platelet-Derived Growth Factor Receptor

  摘要：

  1-Phenylbenzimidazoles are shown to be a new class of ATP-site inhibitors of the platelet-derived growth factor receptor (PDGFR). Structure-activity relationships (SARs) are narrow, with closely related heterocycles being inactive. A systematic study of substituted 1-phenyl-benzimidazoles showed clear SARs. Substituents at the 4'- and 3'-positions of the phenyl ring are tolerated but do not significantly improve activity, while substituents at the 2'-position abolish it. Substituents in the 2-, 4-, and 7-positions of the benzimidazole ring (with the exception of 4-OH) also abolish activity. Most substituents at the 5- and B-positions maintain or increase activity, with the 5-OH, 5-OMe, 5-COMe, and 5-CO2Me analogues being >10-fold more potent than the parent 1-phenylbenzimidazole. The 5-OMe analogue was both the most potent inhibitor, and showed the highest selectivity (50-fold) between PDGFR and FGFR isolated enzymes, and also a moderately effective inhibitor (IC50 = 1.9 mu M) of PDGF-stimulated PDGFR autophosphorylation in rat aorta smooth muscle cells.

  DOI：

  10.1021/jm9804681

文献信息

• Efficient N-arylation of azole compounds utilizing selective aryl-transfer TMP-iodonium(III) reagents
  作者：Daichi Koseki、Erika Aoto、Toshitaka Shoji、Kazuma Watanabe、Yasuko In、Yasuyuki Kita、Toshifumi Dohi

  DOI：10.1016/j.tetlet.2019.04.012

  日期：2019.5

  It was determined that diaryliodonium(III) triflates bearing a trimethoxybenzene (TMP) auxiliary are more reactive than the reported selective aryl-transfer iodonium salts in the N-arylation of benzimidazoles and other types of azole compounds under catalytic conditions. The TMP-iodonium(III) salts can thus effectively facilitate the reaction at 50 °C or below, producing the corresponding N-arylated

  已确定在催化条件下，在苯并咪唑和其他类型的唑化合物的N-芳基化反应中，带有三甲氧基苯（TMP）助剂的二芳基碘鎓（III）三氟甲磺酸盐比报道的选择性芳基转移碘鎓盐更具反应性。因此，TMP-碘鎓（III）盐可以有效地促进在50℃或更低的温度下反应，产生相应的N-芳基化的联芳基，而不会形成TMP-衍生的偶联副产物。在温和的条件下使用该TMP试剂可防止潜在的辅助基团参与偶联反应的问题，这是在使用需要升高温度的碘鎓（III）盐时观察到的。
• Chemoselective Chan-Lam coupling by directly using copper powders via mechanochemical metal activation for catalysis
  作者：Weijia Shi、Yü Shi、Minling Xü、Gang Zou、Xin-Yan Wu

  DOI：10.1016/j.mcat.2022.112472

  日期：2022.8

  been observed, indicating different chemistry under the mechanochemical metal activation for catalysis from that in conventional solution systems. A modified copper(I-II-III) catalytic cycle involving peroxocopper(II) intermediates has been proposed to explain the observed chemistry, in which mono(amido)copper(I) and bis(amido)copper(II) intermediates represent the catalytically active and low or inactive

  通过在甲醇中直接使用催化量的商业铜粉，通过机械化学金属活化进行催化，开发了一种高度化学选择性的（苯并）咪唑、苯胺和烷基胺的 Chan-Lam 偶联，该催化能够整合金属表面活化、催化剂形成和催化。已经观察到 NH 对应物的精细电子效应、芳基硼酸的配位要求以及助催化剂乙酸盐对抑制空气不稳定苯胺氧化分解的独特性能，表明在机械化学金属活化下用于催化的化学反应与常规溶液体系不同. 已经提出了一种涉及过氧铜（II）中间体的改性铜（I-II-III）催化循环来解释观察到的化学反应，
• MEDICINAL COMPOSITION FOR PREVENTION OR TREATMENT OF PARASITIC PROTOZOAN INFECTION
  申请人：Japan Science and Technology Agency

  公开号：EP1800682A1

  公开（公告）日：2007-06-27

  The present invention is to provide a medicinal composition for preventing or treating parasitic protozoan infections, having a high selective toxicity against parasitic protozoan infection, and a superior preventive or treating effect. A medicinal composition for preventing or treating parasitic protozoan infections comprises a compound shown by the following general formula (1) as an active ingredient (wherein R represents an alkyl group, aryl group or heterocyclic group; A and B each independently represents a 5- or 6-membered ring containing at least one hetero atom, or a condensation ring wherein 1 or more 3- to 8-membered ring is condensed thereto; Y represents S, 0, Se, or -NR1-(R1 represents an alkyl group, aryl group or heterocyclic group); L1, L2, L3, L4 and L5 each independently represents a methine group; Q represents a physiologically acceptable anion; k represents an integer of 0 to 2, necessary to make the electric charge of the whole molecule 0; p and q each represents an integer of 0 to 3, wherein the sum of p and q is 1 or more, and 6 or less.)

  本发明旨在提供一种用于预防或治疗寄生性原虫感染的药物组合物，该组合物对寄生性原虫感染具有较高的选择性毒性，并具有优异的预防或治疗效果。一种用于预防或治疗寄生性原生动物感染的药物组合物由以下通式（1）所示的化合物作为活性成分组成 (其中 R 代表烷基、芳基或杂环基团；A 和 B 各自独立地代表含有至少一个杂原子的 5 或 6 元环，或其上缩合有一个或多个 3 至 8 元环的缩合环；Y 代表 S、0、Se 或 -NR1-（R1 代表烷基、芳基或杂环基团）；L1、L2、L3、L4 和 L5 各自独立地代表一个甲基； Q 代表生理上可接受的阴离子； k 代表 0 至 2 的整数，是使整个分子的电荷为 0 所必需的； p 和 q 各自代表 0 至 3 的整数，其中 p 和 q 的和为 1 或以上，6 或以下。)
• ANTI-TRYPANOSOMIASIS AGENT
  申请人：Japan Science and Technology Agency

  公开号：EP1818334A1

  公开（公告）日：2007-08-15

  The present invention is to provide an anti-trypanosomiasis agent having a high selective toxicity, and high preventing or treating effect against trypanosomiasis, comprising a compound shown by the following general formula (1) as an active ingredient (wherein R1 and R2 each independently represents a hydrogen atom, halogen atom, hydroxyl group, oxygen atom, C1-5 alkyl group, C1-5 alkoxy group, C5-8 aryl group, C5-8 aryloxy group, C2-6 alkoxycarbonyl group or C2-6 alkylaminocarbonyl group, and may be bound to each other; R3, R4, and R5 each independently represents a C1-5 alkyl group or C5-8 aryl group; R6 and R7 each independently represents a hydrogen atom, halogen atom, hydroxyl group, oxygen atom, C1-8 alkyl group, C1-5 alkoxy group, C5-8 aryl group, C5-8 aryloxy group, or C2-6 alkoxycarbonyl group, and may be bound to each other; Y and Z each independently represents an atom group necessary to form a 5- or 6-membered heterocycle; m and n each represent 0 or 1; Q represents a physiologically acceptable anion; k represents an integer of 0 to 2, necessary to make the electric charge of the whole molecule 0) .

  本发明旨在提供一种抗锥虫病制剂，它具有高选择性毒性和高预防或治疗锥虫病的效果，其活性成分包括如下通式(1)所示的化合物 (其中 R1 和 R2 各自独立地代表氢原子、卤素原子、羟基、氧原子、C1-5 烷基、C1-5 烷氧基、C5-8 芳基、C5-8 芳氧基、C2-6 烷氧基羰基或 C2-6 烷氨基羰基，并可相互结合；R3、R4 和 R5 各自独立地代表 C1-5 烷基或 C5-8 芳基；R6 和 R7 各自独立地代表氢原子、卤素原子、羟基、氧原子、C1-8 烷基、C1-5 烷氧基、C5-8 芳基、C5-8 芳氧基或 C2-6 烷氧基羰基，并可相互结合；Y 和 Z 各自独立地代表形成 5 或 6 元杂环所必需的原子团； m 和 n 各自代表 0 或 1； Q 代表生理上可接受的阴离子； k 代表 0 至 2 的整数，是使整个分子的电荷为 0 所必需的。
• PHARMACEUTICAL COMPOSITION COMPRISING AZARHODACYANINE COMPOUND AS ACTIVE INGREDIENT
  申请人：Japan Science and Technology Agency

  公开号：EP1894920A1

  公开（公告）日：2008-03-05

  The object of the invention is to provide pharmaceutical composition that can be used as a therapeutic and/or prophylactic agent. Particularly, the pharmaceutical composition of the invention has significant therapeutic effect and survival benefit for the disease caused by parasitic protozoa, and selective toxicity against the causative protozoa. The pharmaceutical composition comprises a compound represented by general formula (1). Particularly, the invention relates to a composition that is an effective therapeutic/prophylactic agent for malaria, leishmania, African sleeping sickness, Chagas disease, toxoplasmosis lymphatic filariasis, babesiosis, and coccidiosis, and a novel compound contained therein.

  本发明的目的是提供可用作治疗和/或预防剂的药物组合物。特别是，本发明的药物组合物对寄生原虫引起的疾病有显著的治疗效果和生存益处，并对致病原虫有选择性毒性。该药物组合物包含通式（1）所代表的化合物。特别是，本发明涉及一种对疟疾、利什曼病、非洲昏睡病、南美锥虫病、弓形虫病淋巴丝虫病、巴贝丝虫病和球虫病具有有效治疗/预防作用的组合物，以及其中所含的一种新型化合物。