吲哚啉-7-羧酸甲酯 | 112106-91-9

• 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: 吲哚啉-7-羧酸甲酯
• 中文别名: 2,3-二氢-1H-吲哚-7-羧酸甲酯
• 英文名称: methyl indoline-7-carboxylate
• 英文别名: methyl 2,3-dihydro-1H-indole-7-carboxylate
• CAS: 112106-91-9
• 化学式: C₁₀H₁₁NO₂
• mdl: MFCD09954772
• 分子量: 177.203
• InChiKey: IMJZMELPOAMWJA-UHFFFAOYSA-N

物化性质

• 熔点：
  69-69.5 °C
• 沸点：
  328.4±31.0 °C(Predicted)
• 密度：
  1.162±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.8
• 重原子数：
  13
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.3
• 拓扑面积：
  38.3
• 氢给体数：
  1
• 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: 1H-Indole-7-carboxylic acid,2,3-dihydro-,methyl ester
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: 1H-Indole-7-carboxylic acid,2,3-dihydro-,methyl ester
CAS number: 112106-91-9

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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: C10H11NO2
Molecular weight: 177.2

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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：

  吲哚啉-7-羧酸甲酯 以 水 为溶剂， 生成 indolin-7-ylmethanol
  参考文献：
  名称：

  US4729998

  摘要：

  公开号：
• 作为产物：
  描述：

  1H-吲哚-7-羧酸甲酯 在 氢气 、 溶剂黄146 作用下， 以 乙醇 、 水 为溶剂， 以96%的产率得到吲哚啉-7-羧酸甲酯
  参考文献：
  名称：

  连续合成半饱和杂环双分子片段的简便流程

  摘要：

  在连续流动条件下进行氢化反应可得到半饱和片段，具有理想的理化特性，并具有合成修饰和与生物靶标结合的关键基序。它们连续不断地轻松进行功能化，为功能化富含sp 3的片段进行多步合成提供了一个有效的机会。

  DOI：

  10.1002/ejoc.201801684

文献信息

• HETEROBICYCLIC AMIDES AS INHIBITORS OF CD38
  申请人：Ribon Therapeutics, Inc.

  公开号：US20210032251A1

  公开（公告）日：2021-02-04

  The present invention relates to heterobicyclic amides and related compounds which are inhibitors of CD38 and are useful in the treatment of cancer.

  本发明涉及杂环酰胺及相关化合物，它们是CD38的抑制剂，可用于治疗癌症。
• [EN] CD38 INHIBITORS AND METHODS OF TREATMENT<br/>[FR] INHIBITEURS DE LA CD38 ET MÉTHODES DE TRAITEMENT
  申请人：GLAXOSMITHKLINE IP NO 2 LTD

  公开号：WO2016087975A1

  公开（公告）日：2016-06-09

  Compounds of Formula (I) and methods of treating diseases of metabolism by modulating cellular NAD+ levels through the inhibition of the CD38 enzyme, are disclosed. Formula (I).

  公式（I）的化合物和通过通过抑制CD38酶调节细胞NAD+水平来治疗代谢性疾病的方法已被披露。公式（I）。
• Structure-Based Design and Preclinical Characterization of Selective and Orally Bioavailable Factor XIa Inhibitors: Demonstrating the Power of an Integrated S1 Protease Family Approach
  作者：Edwige Lorthiois、James Roache、David Barnes-Seeman、Eva Altmann、Ulrich Hassiepen、Gordon Turner、Rohit Duvadie、Viktor Hornak、Rajeshri G. Karki、Nikolaus Schiering、Wilhelm A. Weihofen、Francesca Perruccio、Amy Calhoun、Tanzina Fazal、Darija Dedic、Corinne Durand、Solene Dussauge、Kamal Fettis、Fabien Tritsch、Celine Dentel、Adelaide Druet、Donglei Liu、Louise Kirman、Julie Lachal、Kenji Namoto、Douglas Bevan、Rose Mo、Gabriela Monnet、Lionel Muller、Richard Zessis、Xueming Huang、Loren Lindsley、Treeve Currie、Yu-Hsin Chiu、Cary Fridrich、Peter Delgado、Shuangxi Wang、Micah Hollis-Symynkywicz、Joerg Berghausen、Eric Williams、Hong Liu、Guiqing Liang、Hyungchul Kim、Peter Hoffmann、Andreas Hein、Paul Ramage、Allan D’Arcy、Stefanie Harlfinger、Martin Renatus、Simon Ruedisser、David Feldman、Jason Elliott、Richard Sedrani、Juergen Maibaum、Christopher M. Adams

  DOI：10.1021/acs.jmedchem.0c00279

  日期：2020.8.13

  The serine protease factor XI (FXI) is a prominent drug target as it holds promise to deliver efficacious anticoagulation without an enhanced risk of major bleeds. Several efforts have been described targeting the active form of the enzyme, FXIa. Herein, we disclose our efforts to identify potent, selective, and orally bioavailable inhibitors of FXIa. Compound 1, identified from a diverse library of

  丝氨酸蛋白酶因子XI（FXI）是一个重要的药物靶标，因为它有望提供有效的抗凝作用而不会增加大出血的风险。已经描述了针对酶的活性形式FXIa的几种努力。本文中，我们公开了我们为确定有效，选择性和口服生物利用性FXIa抑制剂而做出的努力。化合物1从内部丝氨酸蛋白酶抑制剂的各种文库中鉴定出来的肽原本被设计为补体因子D抑制剂，并表现出亚微摩尔FXIa活性和令人鼓舞的吸收，分布，代谢和排泄（ADME）特性，同时缺乏拟肽结构。通过基于结构的药物设计和传统药物化学相结合，FXIa的S1，S1β和S1'口袋中相互作用的最优化导致发现具有FXIa亚纳摩尔效价，对其他凝血蛋白酶的选择性增强的化合物23，以及临床前药代动力学（PK）资料与患者的两次给药一致。
• PYRIMIDO-DIAZEPINONE COMPOUNDS AND METHODS OF TREATING DISORDERS
  申请人：DANA-FARBER CANCER INSTITUTE, INC.

  公开号：US20160024115A1

  公开（公告）日：2016-01-28

  The present invention relates to novel pyrimido-diazepinone compounds, methods of modulating protein kinases, including MPS1 (TTK), ERK5 (BMK1, MAPK7), LRKK2, EphA2, polo kinase 1,2,3, or 4, Ack1, Ack2, Abl, DCAMKL1, ABL1, Abl mutants, DCAMKL2, ARK5, BRK, MKNK2, FGFR4, TNK1, PLK1, ULK2, PLK4, PRKD1, PRKD2, PRKD3, ROS1, RPS6KA6, TAOK1, TAOK3, TNK2, Bcr-Abl, GAK, cSrc, TPR-Met, Tie2, MET, FGFR3, Aurora, Axl, Bmx, BTK, c-kit, CHK2, Flt3, MST2, p70S6K, PDGFR, PKB, PKC, Raf, ROCK-H, Rsk1, SGK, TrkA, TrkB and TrkC, and the use of such compounds in the treatment of various diseases, disorders or conditions.

  本发明涉及新型嘧啶二氮杂环庚内酮类化合物，调节蛋白激酶的方法，包括MPS1（TTK）、ERK5（BMK1，MAPK7）、LRKK2、EphA2、polo激酶1、2、3或4、Ack1、Ack2、Abl、DCAMKL1、ABL1、Abl突变体、DCAMKL2、ARK5、BRK、MKNK2、FGFR4、TNK1、PLK1、ULK2、PLK4、PRKD1、PRKD2、PRKD3、ROS1、RPS6KA6、TAOK1、TAOK3、TNK2、Bcr-Abl、GAK、cSrc、TPR-Met、Tie2、MET、FGFR3、Aurora、Axl、Bmx、BTK、c-kit、CHK2、Flt3、MST2、p70S6K、PDGFR、PKB、PKC、Raf、ROCK-H、Rsk1、SGK、TrkA、TrkB和TrkC等蛋白激酶的调节，以及这些化合物在治疗各种疾病、疾病或症状中的使用。
• [EN] ETHYNYL DERIVATIVES<br/>[FR] DÉRIVÉS D'ÉTHYNYLE
  申请人：HOFFMANN LA ROCHE

  公开号：WO2015044075A1

  公开（公告）日：2015-04-02

  The present invention relates to compounds of formula I wherein Y is N or C-R1'; G is a 5 or 6-membered aromatic or heteroaromatic ring containing 0, 1, 2 or 3 heteroatoms, selected from the group consisting of phenyl, pyridinyl with different N-positions, imidazolyl, pyrazinyl, pyrimidinyl, thiophenyl, thiazolyl, pyrazolyl or thiadiazolyl, which are optionally substituted by 1, 2 or 3 substituents, selected from the group consisting of halogen, lower alkyl, lower alkoxy, lower alkoxy substituted by halogen or NRR'; R and R' are independently from each other hydrogen or lower alkyl, or may form together with the N atom to which they are attached a five or six membered saturated heterocyclic group which may contain an additional oxygen, NH, or N-lower alkyl group; R1 is hydrogen, halogen or lower alkyl substituted by halogen; R1' is hydrogen, halogen or lower alkyl substituted by halogen; R2 is hydrogen, lower alkyl, lower alkoxyalkyl, cycloalkyl or heterocycloalkyl; or R2 may form together with the closest carbon atom in group G a group (IA) for A being -CH2-, -CH2CH2, or -C(CH3)2-, R3 is phenyl or pyridinyl, wherein the N atom in the pyridinyl group may be in different positions; or to a pharmaceutically acceptable salt or acid addition salt, to a racemic mixture, or to its corresponding enantiomer and/or optical isomer and/or stereoisomer thereof. It has been surprisingly been found that the compounds of general formula I are positive allosteric modulators (PAMs) of metabotropic glutamate receptor 4 (mGluR4), useful for the treatment of Parkinson's disease, anxiety, emesis, obsessive compulsive disorder, autism, neuroprotection, cancer, depression and diabetes type 2.

  本发明涉及符号I的化合物，其中Y为N或C-R1'；G为含有0、1、2或3个杂原子的5或6元芳香或杂芳环，所选自苯基、带有不同N-位置的吡啶基、咪唑基、吡啶嗪基、嘧啶基、噻吩基、噻唑基、吡唑基或噻二唑基，这些基可以选择性地被1、2或3个卤素、低烷基、低烷氧基、被卤素或NRR'取代；R和R'彼此独立地为氢或低烷基，或者可以与它们连接的N原子一起形成一个含有额外氧、NH或N-低烷基的五元或六元饱和杂环基；R1为氢、卤素或被卤素取代的低烷基；R1'为氢、卤素或被卤素取代的低烷基；R2为氢、低烷基、低烷氧基烷基、环烷基或杂环烷基；或者R2可以与基团G中最近的碳原子一起形成一个(A为-CH2-、-CH2CH2或-C(CH3)2-)的基团(IA)；R3为苯基或吡啶基，其中吡啶基中的N原子可能在不同位置；或者为药学上可接受的盐或酸加合盐，或为外消旋混合物，或为其对应的对映体和/或光学异构体和/或立体异构体。令人惊讶的是发现，一般式I化合物是代谢型谷氨酸受体4(mGluR4)的阳性变构调节剂(PAMs)，对帕金森病、焦虑、呕吐、强迫症、自闭症、神经保护、癌症、抑郁症和2型糖尿病的治疗有用。