4-甲氧基吲哚-2-羧酸 | 103260-65-7

• 物质功能分类: 医药中间体 - 杂环化合物
• 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: 4-甲氧基吲哚-2-羧酸
• 中文别名: 4-甲氧基吲哚-2-甲酸
• 英文名称: 4-methoxy-1H-indole-2-carboxylic acid
• 英文别名: 4-methoxyindole-2-carboxylic acid
• CAS: 103260-65-7
• 化学式: C₁₀H₉NO₃
• mdl: MFCD02664458
• 分子量: 191.186
• InChiKey: ZZAVIQXQBBOHBB-UHFFFAOYSA-N

物化性质

• 熔点：
  234-235 °C
• 沸点：
  447.6±25.0 °C(Predicted)
• 密度：
  1.381±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.9
• 重原子数：
  14
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.1
• 拓扑面积：
  62.3
• 氢给体数：
  2
• 氢受体数：
  3

安全信息

• 危险等级：
  IRRITANT
• 危险品标志：
  Xi
• 危险类别码：
  R36/37/38
• 海关编码：
  2933990090
• 危险类别：
  IRRITANT
• 安全说明：
  S26,S36/37/39
• 危险性防范说明：
  P261,P305+P351+P338
• 危险性描述：
  H315,H319,H335
• 储存条件：
  2～8℃

SDS

Material Safety Data Sheet

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Section 1. Identification of the substance
Product Name: 4-Methoxy-1H-indole-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-Methoxy-1H-indole-2-carboxylic acid
CAS number: 103260-65-7

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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: C10H9NO3
Molecular weight: 191.2

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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：

  4-甲氧基吲哚-2-羧酸 以 喹啉 为溶剂， 反应 0.2h， 以97%的产率得到4-甲氧基吲哚
  参考文献：
  名称：

  Decarboxylation of indole-2-carboxylic acids: improved procedures

  摘要：

  DOI：

  10.1021/jo00072a052
• 作为产物：
  描述：

  pyruvic acid 在 氨 、 iron(II) sulfate 作用下， 生成 4-甲氧基吲哚-2-羧酸
  参考文献：
  名称：

  Blaikie; Perkin, Journal of the Chemical Society, 1924, vol. 125, p. 313

  摘要：

  DOI：

文献信息

• [EN] INHIBITORS OF NOROVIRUS AND CORONAVIRUS REPLICATION<br/>[FR] INHIBITEURS DE LA RÉPLICATION DE NOROVIRUS ET DE CORONAVIRUS
  申请人：COCRYSTAL PHARMA INC

  公开号：WO2021206876A1

  公开（公告）日：2021-10-14

  Compounds of Formula (I) and methods of inhibiting the replication of viruses in a biological sample or patient, of reducing the amount of viruses in a biological sample or patient, and of treating a virus infection in a patient, comprising administering to said biological sample or patient an effective amount of a compound represented by Formula (I), a compound of Table A or B or a pharmaceutically acceptable salt thereof.

  公式（I）化合物及抑制生物样本或患者中病毒复制、减少生物样本或患者中病毒数量、以及治疗患者病毒感染的方法，包括向所述生物样本或患者投与由公式（I）表示的化合物、表A或B中的化合物或其药用可接受盐的有效量。
• [EN] SUBSTITUTED TRICYCLIC AMIDES, ANALOGUES THEREOF, AND METHODS USING SAME<br/>[FR] AMIDES TRICYCLIQUES SUBSTITUÉS, ANALOGUES DE CEUX-CI ET PROCÉDÉS LES METTANT EN OEUVRE
  申请人：ARBUTUS BIOPHARMA CORP

  公开号：WO2021229302A1

  公开（公告）日：2021-11-18

  The present disclosure includes substituted tricyclic amides, or analogues thereof of formula (I) (I), wherein X, Y, ring A, R1, R5, R6 and R7 are as defined herein, and compositions comprising compounds of formula (I) that can be used to treat or prevent hepatitis B virus (HBV) and/or hepatitis D virus (HDV) infections in a patient.

  本公开涵盖了替代三环酰胺，或其类似物的化合物，其化学式为(I)，其中X、Y、环A、R1、R5、R6和R7如本文所定义，并包括化合物(I)的组合物，可用于治疗或预防患者体内的乙型肝炎病毒（HBV）和/或丙型肝炎病毒（HDV）感染。
• Design, synthesis and evaluation of novel indole-2-carboxamides for growth inhibition of <i>Mycobacterium tuberculosis</i> and paediatric brain tumour cells
  作者：Shahinda S. R. Alsayed、Shichun Lun、Anders W. Bailey、Amreena Suri、Chiang-Ching Huang、Mauro Mocerino、Alan Payne、Simone Treiger Sredni、William R. Bishai、Hendra Gunosewoyo

  DOI：10.1039/d0ra10728j

  日期：——

  In this study, we demonstrated that an indoleamide scaffold can be fine-tuned to confer a set of derivatives with selective antitubercular and/or antitumour activities.

  在这项研究中，我们展示了一种吲哚酰胺支架可以被微调，以赋予一组衍生物具有选择性抗结核和/或抗肿瘤活性。
• Design, synthesis and antimycobacterial evaluation of novel adamantane and adamantanol analogues effective against drug-resistant tuberculosis
  作者：Shahinda S.R. Alsayed、Shichun Lun、Alan Payne、William R. Bishai、Hendra Gunosewoyo

  DOI：10.1016/j.bioorg.2020.104486

  日期：2021.1

  Remarkably, the most potent adamantanol analogue 8j demonstrated high selectivity towards DS and DR M. tb strains over mammalian cells [IC50 (Vero cells) ≥ 169 µM], evincing its lack of cytotoxicity. The top eight active compounds 8b, 8d, 8f, 8i, 8j, 8k, 8l and 10a retained their in vitro potency against DR M. tb strains and were docked into the MmpL3 active site. The most potent adamantanol/adamantane-based

  结核病 (TB) 的危险性质与普遍存在的耐药 (DR) 形式相结合，使这种疾病成为日益严重的公共卫生威胁。因此，开发具有新作用机制的新型化疗药物以规避交叉耐药性问题势在必行。结核分枝杆菌( M. tb ) 外膜的独特结构在其发病机制中起主要作用，有助于其对可用治疗剂的内在抗性。分枝杆菌膜蛋白大3（MmpL3），这是在锻造的关键角色的结核分枝杆菌刚性细胞壁，代表了结核病药物开发的一个新兴目标。之前在我们的小组中发现了几种 indole-2-carboxamides 作为有效的抗结核药物，可作为 MmpL3 转运蛋白的抑制剂。尽管它们在体外具有很强的活性，但这些吲哚酰胺的致命弱点可以归因于它们的高亲脂性和低水溶性。在这项研究中，我们报告了我们尝试提高这些 indole-2-carboxamides 的水溶性，同时保持足够的亲脂性以允许有效的结核分枝杆菌细胞壁渗透。将极性更强的金刚烷醇部分并入几
• CBI analogues of the duocarmycins and CC-1065
  申请人：Boger L. Dale

  公开号：US20050026987A1

  公开（公告）日：2005-02-03

  An extensive series of CBI analogues of the duocarmycins and CC-1065 exploring substituent effects within the first indole DNA binding subunit is detailed. In general, substitution at the indole C5 position led to cytotoxic potency enhancements that can be ≧1000-fold providing simplified analogues containing a single DNA binding subunit that are more potent (IC 50 =2-3 pM) than CBI-TMI, duocarmycin SA, or CC-1065. The increases in cytotoxicity correlate well with accompanying increases in the rate and efficiency of DNA alkylation. This effect is more pronounced with the CBI versus DSA or CPI based analogues. Moreover, this effect is largely insensitive to the electronic character of the C5 substituent but is sensitive to the size, rigid length, and shape (sp, sp 2 , sp 3 hybridization) of this substituent consistent with expectation that the impact is due simply to its presence.

  一系列广泛的CBI类似物，包括二聚卡蜜素和CC-1065的类似物，探索了第一个吲哚DNA结合亚基中取代基效应的细节。一般来说，在吲哚C5位置的取代导致细胞毒性增强，可以达到≧1000倍，提供了更强效（IC50=2-3 pM）的含有单个DNA结合亚基的简化类似物，比CBI-TMI、二聚卡蜜素SA或CC-1065更有效。细胞毒性增加与DNA烷基化速率和效率的增加密切相关。与基于DSA或CPI的类似物相比，这种效应在CBI类似物中更为显著。此外，这种效应对于C5取代基的电子性质不太敏感，但对于取代基的大小、刚性长度和形状（sp、sp2、sp3杂化）敏感，这与预期一致，即这种影响仅仅是由于其存在。