6-氯吲哚-2-羧酸 | 16732-75-5

• 物质功能分类: 医药中间体 - 吲哚类化合物
• 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: 6-氯吲哚-2-羧酸
• 中文别名: 6-氯吲哚-2-甲酸；6-氯-1H-吲哚-2-羧酸
• 英文名称: 6-chloro-1H-indole-2-carboxylic acid
• 英文别名: 6-chloroindole-2-carboxylic acid；6-Chlor-indol-2-carbonsaeure
• CAS: 16732-75-5
• 化学式: C₉H₆ClNO₂
• mdl: MFCD01863157
• 分子量: 195.605
• InChiKey: BKPSJOSKWKTWAG-UHFFFAOYSA-N

物化性质

• 熔点：
  248-249 °C
• 沸点：
  449.7±25.0 °C(Predicted)
• 密度：
  1.548±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  13
• 可旋转键数：
  1
• 环数：
  2.0
• 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

• 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
• 危险性防范说明：
  P261,P305+P351+P338
• 危险性描述：
  H315,H319,H335
• 储存条件：
  应存于室温、避光、干燥且密封的环境中。

SDS

Material Safety Data Sheet

---

Section 1. Identification of the substance
Product Name: 6-Chloroindole-2-carboxylic acid
Synonyms:

---

Section 2. Hazards identification
Harmful by inhalation, in contact with skin, and if swallowed.

---

Section 3. Composition/information on ingredients.
Ingredient name: 6-Chloroindole-2-carboxylic acid
CAS number: 16732-75-5

---

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.

---

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.

---

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.

---

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:

---

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.

---

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: C9H6ClNO2
Molecular weight: 195.6

---

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.

---

Section 11. Toxicological information
No data.

---

Section 12. Ecological information
No data.

---

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.

---

Section 14. Transportation information
Non-harzardous for air and ground transportation.

---

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.

---

SECTION 16 - ADDITIONAL INFORMATION
N/A

反应信息

• 作为反应物：
  描述：

  6-氯吲哚-2-羧酸 在 吡啶 、 正丁基锂 、 氯化亚砜 、 manganese(III) triacetate dihydrate 、 溶剂黄146 作用下， 以 四氢呋喃 、 正己烷 、 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 10.08h， 生成 diethyl 2-acetoxy-2-[6-chloro-2-(3-fluorobenzoyl)-1H-indol-3-yl]malonate
  参考文献：
  名称：

  新型和多种环氧合酶2抑制剂作为抗炎药的设计，合成及构效关系研究。

  摘要：

  由于环氧合酶（COX）在炎症过程中的关键作用，抑制COX活性的非甾体类抗炎药（NSAIDs）已在临床上用于治疗炎症性疾病/综合征。然而，传统的非甾体类抗炎药由于抑制COX-1而表现出严重的副作用，如胃肠道损害和超敏反应。同样，COX-2抑制性对各种癌症/肿瘤（例如结肠癌，胃癌，皮肤癌，皮肤癌，肺癌，肝癌，胰腺癌，乳腺癌，前列腺癌，宫颈癌和卵巢癌）的起始/增殖/侵袭/运动/复发/转移的抑制或预防作用癌症很重要。在这项研究中，设计，合成和各种新型{2-[（2-，3-和/或4-取代）-苯甲酰基，结构-活性关系（SAR）（双环杂环烷苯基）羰基或环烷羰基]-（5-或6-取代）-1H-吲哚-3-基}乙酸类似物的研究旨在寻找和鉴定各种有效的和选择性的COX-2抑制剂，用于治疗炎症疾病，导致在外周炎症模型大鼠中发现口服有效药物。SAR和类似物的理化特性被描述为重要发现。有关图形摘要：请参阅补充材料。（www

  DOI：

  10.3109/14756366.2013.864650
• 作为产物：
  描述：

  6-chloro-1-(phenylsulfonyl)-1H-indole-2-carboxylic acid 在 sodium hydroxide 、 盐酸 作用下， 以 乙醇 、 水 为溶剂， 反应 11.0h， 以95%的产率得到6-氯吲哚-2-羧酸
  参考文献：
  名称：

  新型和多种环氧合酶2抑制剂作为抗炎药的设计，合成及构效关系研究。

  摘要：

  由于环氧合酶（COX）在炎症过程中的关键作用，抑制COX活性的非甾体类抗炎药（NSAIDs）已在临床上用于治疗炎症性疾病/综合征。然而，传统的非甾体类抗炎药由于抑制COX-1而表现出严重的副作用，如胃肠道损害和超敏反应。同样，COX-2抑制性对各种癌症/肿瘤（例如结肠癌，胃癌，皮肤癌，皮肤癌，肺癌，肝癌，胰腺癌，乳腺癌，前列腺癌，宫颈癌和卵巢癌）的起始/增殖/侵袭/运动/复发/转移的抑制或预防作用癌症很重要。在这项研究中，设计，合成和各种新型{2-[（2-，3-和/或4-取代）-苯甲酰基，结构-活性关系（SAR）（双环杂环烷苯基）羰基或环烷羰基]-（5-或6-取代）-1H-吲哚-3-基}乙酸类似物的研究旨在寻找和鉴定各种有效的和选择性的COX-2抑制剂，用于治疗炎症疾病，导致在外周炎症模型大鼠中发现口服有效药物。SAR和类似物的理化特性被描述为重要发现。有关图形摘要：请参阅补充材料。（www

  DOI：

  10.3109/14756366.2013.864650

文献信息

• [EN] PYRAZOLOSPIROKETONE ACETYL-C0A CARBOXYLASE INHIBITORS<br/>[FR] INHIBITEURS DE LA PYRAZOLOSPIROCÉTONE ACÉTL-COA CARBOXYLASE
  申请人：PFIZER

  公开号：WO2009144554A1

  公开（公告）日：2009-12-03

  The invention provides compounds of Formula (1) or a pharmaceutically acceptable salt of said compound, wherein R1, R2, and R3 are as described herein; pharmaceutical compositions thereof; and the use thereof in treating diseases, conditions or disorders modulated by the inhibition of acetyl-CoA carboxylase enzyme(s) in an animal.

  本发明提供了式(1)的化合物或所述化合物的药用可接受盐，其中R1、R2和R3如本文所述；其药物组合物；以及用于治疗通过抑制动物中的乙酰辅酶A羧化酶酶活性来调节的疾病、病症或障碍的使用方法。
• [EN] FUSED RING PYRIMIDONE DERIVATIVES FOR USE IN THE TREATMENT OF HBV INFECTION OR OF HBV-INDUCED DISEASES<br/>[FR] DÉRIVÉS DE PYRIMIDONE À CYCLES FUSIONNÉS DESTINÉS À ÊTRE UTILISÉS DANS LE TRAITEMENT D'UNE INFECTION PAR LE VIRUS DE L'HÉPATITE B OU DE MALADIES INDUITES PAR LE VIRUS DE L'HÉPATITE B
  申请人：JANSSEN SCIENCES IRELAND UNLIMITED CO

  公开号：WO2020182990A1

  公开（公告）日：2020-09-17

  The present application relates to compounds according to Formula (I), pharmaceutical compositions comprising at least one of said compounds, their use as a medicament, and their use in treating chronic hepatitis B virus (HBV) infection. The disclosure further pertains to methods for preparing compounds according to Formula (I).

  本申请涉及按照式(I)的化合物，包括至少一种所述化合物的药物组合物，其作为药物的用途，以及其在治疗慢性乙型肝炎病毒（HBV）感染中的用途。该公开还涉及按照式(I)制备化合物的方法。
• Indole nitriles
  申请人：Roche Palo Alto LLC

  公开号：US06759428B2

  公开（公告）日：2004-07-06

  Compounds of the formula (I) wherein m, n, R1, R2, R3, R4, R5 and R6 are as described herein, together with methods for making the compounds and using the compounds for treatment of diseases or conditions mediated by Cathepsin K.

  公式(I)的化合物： 其中m、n、R1、R2、R3、R4、R5和R6如本文所述，以及制造这些化合物的方法以及使用这些化合物治疗由组织蛋白酶K介导的疾病或病症的方法。
• Optimization of Peptidomimetics as Selective Inhibitors for the β-Catenin/T-Cell Factor Protein–Protein Interaction
  作者：Zhen Wang、Min Zhang、Jin Wang、Haitao Ji

  DOI：10.1021/acs.jmedchem.9b00147

  日期：2019.4.11

  64 and 0.44 μM, respectively, and exhibit good selectivity for β-catenin/Tcf over β-catenin/E-cadherin and β-catenin/adenomatous polyposis coli (APC) PPIs. The 3-(4,5-dimethylthiazol-2-yl)-5-(3-carboxymethoxyphenyl)-2-(4-sulfophenyl)-2 H-tetrazolium (MTS) cell viability assays revealed that 56, the ethyl ester of 53, was more potent than 53 in inhibiting viability of most of the Wnt/β-catenin hyperactive

  β-catenin/ T细胞因子（Tcf）蛋白质-蛋白质相互作用（PPI）在β-catenin信号通路中起着至关重要的作用，而该信号通路在许多癌症和纤维化中均被过度激活。基于旨在靶向β-catenin的Tcf4 G13ANDE17结合位点的化合物1，进行了广泛的结构-活性关系研究。结果，发现化合物53和57分别破坏Ki-值为0.64和0.44μM的β-catenin/ Tcf PPI，并且相对于β-catenin/ E-cadherin和β-catenin/ E-cadherin表现出良好的选择性。 β-catenin/腺瘤性息肉病（APC）PPI。3-（4,5-二甲基噻唑-2-基）-5-（3-羧基甲氧基苯基）-2-（4-磺基苯基）-2 H-四唑（MTS）细胞活力测定显示56，53的乙酯，在抑制大多数Wnt /β-catenin过度活跃的癌细胞的生存力上，它比53更有效。进一步的基于细胞的研究表明56破坏了β-catenin/
• [EN] INDOLE CARBOXAMIDE DERIVATIVES AND USES THEREOF<br/>[FR] DÉRIVÉS D'INDOLE CARBOXAMIDE ET LEURS UTILISATIONS
  申请人：NOVARTIS AG

  公开号：WO2014037900A1

  公开（公告）日：2014-03-13

  A compound of Formula (I) is provided that has been shown to be useful for treating a disease, disorder or syndrome that is mediated by the transportation of essential molecules in the mmpL3 pathway: (I) wherein R1, R2, R3, R4, R5 and R6 are as defined herein.

  提供了一种化合物，其化学式为（I），已被证明对治疗通过mmpL3途径中的必需分子的运输介导的疾病、紊乱或综合症具有益处：（I）其中R1、R2、R3、R4、R5和R6如本文所定义。