(2-甲基-1-吲哚)-乙酸 | 86704-55-4

• 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: (2-甲基-1-吲哚)-乙酸
• 英文名称: 2-(2-methyl-1H-indol-1-yl)acetic acid
• 英文别名: (2-Methylindol-1-yl)acetic acid；2-(2-methylindol-1-yl)acetic acid
• CAS: 86704-55-4
• 化学式: C₁₁H₁₁NO₂
• mdl: MFCD01179130
• 分子量: 189.214
• InChiKey: MGICLRNAZXDKAT-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  14
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.181
• 拓扑面积：
  42.2
• 氢给体数：
  1
• 氢受体数：
  2

安全信息

• 危险等级：
  IRRITANT
• 危险品标志：
  Xi
• 海关编码：
  2933990090

SDS

Material Safety Data Sheet

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Section 1. Identification of the substance
Product Name: (2-Methylindol-1-yl)acetic 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: (2-Methylindol-1-yl)acetic acid
CAS number: 86704-55-4

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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: C11H11NO2
Molecular weight: 189.2

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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：

  (2-甲基-1-吲哚)-乙酸 在 4-二甲氨基吡啶 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 、 N,N-二异丙基乙胺 、 N,N'-二环己基碳二亚胺 作用下， 以 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 35.0h， 生成 N-(3,5-dimethyl-1-phenyl-1H-pyrazol-4-yl)-2-(2-(2-methyl-1H-indol-1-yl)acetamido)acetamide
  参考文献：
  名称：

  Depsipeptides Featuring a Neutral P1 Are Potent Inhibitors of Kallikrein-Related Peptidase 6 with On-Target Cellular Activity

  摘要：

  Kallikrein-related peptidase 6 (KLK6) is a secreted serine protease that belongs to the family of tissue kallikreins (KLKs). Many KLKs are investigated as potential biomarkers for cancer as well as therapeutic drug targets for a number of pathologies. KLK6, in particular, has been implicated in neurodegenerative diseases and cancer, but target validation has been hampered by a lack of selective inhibitors. This work introduces a class of depsipeptidic KLK6 inhibitors, discovered via high-throughput screening, which were found to function as substrate mimics that transiently acylate the catalytic serine of KLK6. Detailed structure-activity relationship studies, aided by in silico modeling, uncovered strict structural requirements for potency, stability, and acyl-enzyme complex half-life. An optimized scaffold, DKFZ-251, demonstrated good selectivity for KLK6 compared to other KLKs, and on-target activity in a cellular assay. Moreover, DKFZ-633, an inhibitor-derived activity based probe, could be used to pull down active endogenous KLK6.

  DOI：

  10.1021/acs.jmedchem.8b01106
• 作为产物：
  描述：

  dicyclohexylammonium (2-methyl-1-indolyl)acetate 在 potassium hydrogensulfate 作用下， 以 二氯甲烷 为溶剂， 生成 (2-甲基-1-吲哚)-乙酸
  参考文献：
  名称：

  的解块Ó硫氰酸铵-Nitrophenylsulfenyl保护的肽和（2-甲基-1-吲哚基）乙酸

  摘要：

  所述的硫氰酸盐裂解Ñ一个- ö -nitrophenylsulfenyl组从在溶液中或在固体载体上的肽在（2-甲基-1-吲哚基）乙酸的存在下有效地进行。该清除剂是由2-甲基吲哚和溴乙酸钠制得的。裂解反应后，可通过用碱与（2-甲基-3-（2-硝基苯硫基）-1-吲哚基）乙酸一起萃取而轻松除去。

  DOI：

  10.1002/hlca.19830660219
• 作为试剂：
  描述：

  N-Ε-苄氧羰基-L-赖氨酸叔丁酯盐酸盐 在 palladium on activated charcoal sodium hydroxide 、 氢气 、 硫氰酸铵 、 1-羟基苯并三唑 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 、 (2-甲基-1-吲哚)-乙酸 、 N,N'-二环己基碳二亚胺 作用下， 以 四氢呋喃 、 1,4-二氧六环 、 甲醇 、 二氯甲烷 、 水 、 溶剂黄146 、 二甲基亚砜 为溶剂， 反应 16.0h， 生成 εAhx-Lys(OBu-t)-Adip-Gly-OSuco
  参考文献：
  名称：

  Luscher, European Journal of Medicinal Chemistry, 1984, vol. 19, # 4, p. 293 - 299

  摘要：

  DOI：

文献信息

• CHEMICAL SUBSTANCES WHICH INHIBIT THE ENZYMATIC ACTIVITY OF HUMAN KALLIKREIN-RELATED PEPTIDASE 6 (KLK6)
  申请人：Deutsches Krebsforschungszentrum

  公开号：EP3305781A1

  公开（公告）日：2018-04-11

  The invention relates to compounds which are suitable for the treatment of a disease associated with kallikrein-like peptidase 6 overexpression and to pharmaceutical compositions containing such compounds. The invention further relates to a kit of parts comprising such compounds or pharmaceutical compositions.

  这项发明涉及适用于治疗与kallikrein样肽酶6过度表达相关疾病的化合物，以及含有这些化合物的药物组合物。该发明还涉及包括这些化合物或药物组合物的配套工具包。
• New CRTh2 antagonists.
  申请人：Almirall, S.A.

  公开号：EP2548863A1

  公开（公告）日：2013-01-23

  The present invention relates to compounds of formula (I), to the process for preparing such compounds and to their use in the treatment of a pathological condition or disease susceptible to amelioration by CRTh2 antagonist activity.

  这项发明涉及到式(I)化合物，制备这种化合物的方法以及它们在治疗病理状况或疾病中的应用，这些病理状况或疾病对CRTh2拮抗活性有改善作用。
• Synthesis of indole-tethered [1,3,4]thiadiazolo and [1,3,4]oxadiazolo[3,2-a]pyrimidin-5-one hybrids as anti-pancreatic cancer agents
  作者：Lalitha Gummidi、Nagaraju Kerru、Paul Awolade、Asif Raza、Arun K. Sharma、Parvesh Singh

  DOI：10.1016/j.bmcl.2020.127544

  日期：2020.11

  activity in vitro. The [1,3,4]oxadiazolo[3,2-a]pyrimidin-5-one hybrids (9a-e) showed stronger anti-pancreatic cancer activity than the [1,3,4]thiadiazolo[3,2-a]pyrimidin-5-one hybrids (8a-j) against the PANC-1 cell line. Compound 9d bearing an ortho-chlorophenyl moiety emerged as the most potent anti-pancreatic cancer agent with an IC50 value of 7.7 ± 0.4 µM, much superior to the standard drug Gemcitabine

  新的吲哚系[1,3,4]噻二唑[3,2 - a ]嘧啶-5-酮（8a - j）和[1,3,4]恶二唑[3,2 - a ]嘧啶-5-酮杂种（9a-e）使用功能化的1,3-二氮杂丁-1,3-二烯与吲哚-乙烯酮的[4 + 2]环加成反应合成。所有分子杂种均通过光谱技术（IR，NMR和HRMS）进行结构表征，并筛选其体外抗胰腺癌活性。[1,3,4]恶二唑[3,2 - a ]嘧啶-5-酮杂种（9a-e）显示出比[1,3,4]噻二唑[3,2- a ]更强的抗胰腺癌活性。] pyrimidin-5-one杂种（8a-j）针对PANC-1细胞系。带有邻氯苯基部分的化合物9d以最强效的抗胰腺癌药物出现，其IC 50值为7.7±0.4 µM，大大优于标准药物吉西他滨（IC 50  > 500 µM）。这些[1,3,4]噻二唑和[1,3,4]恶二唑[3,2 - a ]嘧啶-5-酮杂化物的发现激发了它们作为胰腺癌化学疗法的潜在候选者的潜力。
• [EN] INDOLES AND THEIR THERAPEUTIC USE<br/>[FR] INDOLES ET LEUR UTILISATION THÉRAPEUTIQUE
  申请人：ARGENTA DISCOVERY LTD

  公开号：WO2009077728A1

  公开（公告）日：2009-06-25

  Compound of formula (I) are are ligands of the CRTH2 receptor, useful inter alia for treatment of inflammatory conditions. Wherein X is -SO2- or *-SO2NR3- wherein the bond marked with an asterisk is attached to Ar1; R1 is hydrogen, fluoro, chloro, CN or CF3; R2 is hydrogen, fluoro or chloro; R3 is hydrogen, C1C8alkyl or C3-C7cycloalkyl; Ar1 is phenyl or a 5- or 6-membered heteroaryl group selected from furanyl, thienyl, oxazolyl, thiazolyl, imidazolyl, pyrazolyl, isoxazolyl, isothiazolyl, pyridinyl, pyridazinyl, pyrimidinyl and pyrazinyl, wherein the phenyl or heteroaryl groups are optionally substituted by one or more substituents independently selected from fluoro, chloro, CN, C3- C7cycloalkyl, -O(C1-C4alkyl) or C1C6alkyl, the latter two groups being optionally substituted by one or more fluoro atoms; and Ar2 is phenyl or 5- or 6-membered heteroaryl group selected from pyrrolyl, furanyl, thienyl, oxazolyl, thiazolyl, imidazolyl, pyrazolyl, isoxazolyl, isothiazolyl, pyridinyl, pyridazinyl, pyrimidinyl and pyrazinyl, wherein the phenyl or heteroaryl groups are optionally substituted by one or more substituents independently selected from fluoro, chloro, CN, C3- C3- C7cycloalkyl, -O(C1-C4alkyl) or C1C6alkyl, the latter two groups being optionally substituted by one or more fluoro atoms.

  式(I)的化合物是CRTH2受体的配体，尤其适用于治疗炎症性疾病。其中，X为-SO2-或*-SO2NR3-，其中带有星号的键连接到Ar1；R1为氢、氟、氯、氰基或三氟甲基；R2为氢、氟或氯；R3为氢、C1-C8烷基或C3-C7环烷基；Ar1为苯基或选自呋喃基、噻吩基、噁唑基、噻唑基、咪唑基、吡唑基、异噁唑基、异噻唑基、吡啶基、吡嗪基、嘧啶基和哒嗪基的5或6元杂芳基，其中苯基或杂芳基可任选地被一个或多个独立选自氟、氯、氰基、C3-C7环烷基、-O(C1-C4烷基)或C1-C6烷基的取代基取代，后两个基团可任选地被一个或多个氟原子取代；Ar2为苯基或选自吡咯基、呋喃基、噻吩基、噁唑基、噻唑基、咪唑基、吡唑基、异噁唑基、异噻唑基、吡啶基、吡嗪基、嘧啶基和哒嗪基的5或6元杂芳基，其中苯基或杂芳基可任选地被一个或多个独立选自氟、氯、氰基、C3-C7环烷基、-O(C1-C4烷基)或C1-C6烷基的取代基取代，后两个基团可任选地被一个或多个氟原子取代。
• [EN] COMPOUNDS FOR THE TREATMENT OF HIV<br/>[FR] COMPOSÉS POUR TRAITER LE VIH
  申请人：GILEAD SCIENCES INC

  公开号：WO2013006738A1

  公开（公告）日：2013-01-10

  The invention provides compounds of formula (I): or a salt thereof as described herein. The invention also provides pharmaceutical compositions comprising a compound of formula (I), processes for preparing compounds of formula (I), intermediates useful for preparing compounds of formula I and therapeutic methods for treating a Retroviridae viral infection including an infection caused by the HIV virus.

  本发明提供了如下式（I）的化合物或其盐，还提供了包含如下式（I）化合物的药物组合物，制备如下式（I）化合物的方法，用于制备如下式（I）化合物的中间体以及治疗Retroviridae病毒感染的治疗方法，包括由HIV病毒引起的感染。