2,8-二甲基-2,3,4,5-四氢-1H-吡啶并[4,3-b]吲哚 | 19686-05-6

• 物质功能分类: 医药中间体 - 杂环化合物 - 吡啶类化合物
• 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: 2,8-二甲基-2,3,4,5-四氢-1H-吡啶并[4,3-b]吲哚
• 英文名称: 2.8-dimethyl-2,3,4,5-tetrahydro-1H-pyrido[4,3-b]indole
• 英文别名: 2,3,4,5-tetrahydro-2,8-dimethyl-1H-pyrido[4,3-b]indole；2,8-Dimethyl-2,3,4,5-tetrahydro-1H-pyrido[4,3-b]indole；2,8-dimethyl-1,3,4,5-tetrahydropyrido[4,3-b]indole
• CAS: 19686-05-6
• 化学式: C₁₃H₁₆N₂
• mdl: MFCD00452533
• 分子量: 200.283
• InChiKey: MUZFLDUALLSEBH-UHFFFAOYSA-N

物化性质

• 熔点：
  98-100 °C
• 沸点：
  342.1±37.0 °C(Predicted)
• 密度：
  1.137±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  15
• 可旋转键数：
  0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  19
• 氢给体数：
  1
• 氢受体数：
  1

安全信息

• 危险等级：
  IRRITANT
• 海关编码：
  2933990090

SDS

Material Safety Data Sheet

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Section 1. Identification of the substance
Product Name: 2,8-dimethyl-2,3,4,5-tetrahydro-1H-pyrido[4,3-b]indole
Synonyms: 2,8-Dimethyl-1H,3H,4H,5H-pyrido[4,3-b]indole

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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: 2,8-dimethyl-2,3,4,5-tetrahydro-1H-pyrido[4,3-b]indole
CAS number: 19686-05-6

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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: C13H16N2
Molecular weight: 200.3

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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：

  2,8-二甲基-2,3,4,5-四氢-1H-吡啶并[4,3-b]吲哚 在 盐酸 作用下， 以 甲醇 、 水 为溶剂， 反应 16.0h， 以15%的产率得到2,8-Dimethyl-2,3,4,5-tetrahydro-1H-pyrido[4,3-b]indole hydrochloride
  参考文献：
  名称：

  PYRIDOINDOLE MODULATORS OF NMDA RECEPTOR AND ACETYLCHOLINESTERASE

  摘要：

  本发明涉及新的吡啶吲哚调节NMDA受体、AMPA受体和/或L型钙通道，和/或抑制乙酰胆碱酯酶的药物组合物，以及其使用方法。

  公开号：

  US20100125085A1
• 作为产物：
  描述：

  1-methyl-3-(2-azido-5-methylphenyl)pyridinium triflate 在 sodium tetrahydroborate 、 dirhodium(II) tetrakis(perfluorobutyrate) 作用下， 以 甲醇 、 水 、 甲苯 为溶剂， 反应 15.0h， 生成 2,8-二甲基-2,3,4,5-四氢-1H-吡啶并[4,3-b]吲哚
  参考文献：
  名称：

  钌催化芳基叠氮化物形成 γ-碳鎓离子；二甲酚的合成

  摘要：

  通过 3-吡啶基取代的芳基叠氮化物的钌 (III) 催化反应，立体选择性地生产一系列 γ-咔啉。其他催化剂和条件既没有那么选择性，也没有那么高产率。该方法用于简洁、高效地合成二甲苯啉。

  DOI：

  10.1021/ol2008268

文献信息

• New Route of BenzyneCyclization for Synthesis of 2,3,4,5-Tetrahydro-1H-pyrido[4,3-b]indole Derivatives Avoiding Highly Toxic Aryl Hydrazines
  作者：Lucia Kovacikova、Milan Stefek

  DOI：10.1002/jhet.2150

  日期：2014.9

  A new route for the regioselective synthesis of 2,3,4,5‐tetrahydro‐1H‐pyrido[4,3‐b]indole derivatives was developed based on cyclization of 3‐chlorophenylimine‐N‐alkyl‐4‐piperidones by “the complex bases” of NaNH2 or KNH2. The procedure was performed under variable reaction conditions in inert proton‐free solvents, such as THF, dioxane, 1,2‐dimethoxyethane, toluene, and xylene, at temperatures varying

  基于3-氯苯基亚胺-N-烷基-4-哌啶酮的环化作用，开发了一种新的区域选择性合成2,3,4,5-四氢-1H-吡啶并[4,3-b]吲哚衍生物的新途径。 NaNH 2或KNH 2的“复杂碱基” 。该程序是在可变的反应条件下，在惰性无质子溶剂（例如THF，二恶烷，1,2-二甲氧基乙烷，甲苯和二甲苯）中，在20°C至所用溶剂的沸点之间变化的温度下进行的。避免了在经典的Fischer吲哚合成中出现的有毒芳基肼中间体。
• [EN] PYRIDO (4,3-B) INDOLES CONTAINING RIGID MOIETIES<br/>[FR] PYRIDO[4,3-B]INDOLES CONTENANT DES FRAGMENTS RIGIDES
  申请人：MEDIVATION TECHNOLOGIES INC

  公开号：WO2010051501A1

  公开（公告）日：2010-05-06

  This disclosure is directed to pyrido[4,3-b]indoles having rigid moieties. The compounds in one embodiment are pyrido[4,3-b]indoles having an unsaturated hydrocarbon moiety. The compounds in another embodiment are pyrido[4,3-b]indoles having a cycloalkyl, cycloalkenyl or heterocyclyl moiety. Pharmaceutical compositions comprising the compounds are also provided, as are methods of using the compounds in a variety of therapeutic applications, including the treatment of a cognitive disorder, psychotic disorder, neurotransmitter-mediated disorder and/or a neuronal disorder.

  本公开涉及具有刚性基团的吡啶并[4,3-b]吲哚化合物。在一个实施例中，这些化合物是具有不饱和碳氢基团的吡啶并[4,3-b]吲哚化合物。在另一个实施例中，这些化合物是具有环烷基、环烯基或杂环基团的吡啶并[4,3-b]吲哚化合物。还提供了包括这些化合物的药物组合物，以及使用这些化合物在各种治疗应用中的方法，包括治疗认知障碍、精神障碍、神经递质介导的障碍和/或神经元障碍。
• Design and Synthesis of Neuroprotective Methylthiazoles and Modification as NO-Chimeras for Neurodegenerative Therapy
  作者：Zhihui Qin、Jia Luo、Lawren VandeVrede、Ehsan Tavassoli、Mauro Fa’、Andrew F. Teich、Ottavio Arancio、Gregory R. J. Thatcher

  DOI：10.1021/jm300353r

  日期：2012.8.9

  Learning and memory deficits in Alzheimer’s disease (AD) result from synaptic failure and neuronal loss, the latter caused in part by excitotoxicity and oxidative stress. A therapeutic approach is described that uses NO-chimeras directed at restoration of both synaptic function and neuroprotection. 4-Methylthiazole (MZ) derivatives were synthesized, based upon a lead neuroprotective pharmacophore acting

  阿尔茨海默病 (AD) 的学习和记忆缺陷由突触衰竭和神经元丢失引起，后者部分由兴奋性毒性和氧化应激引起。描述了一种治疗方法，它使用 NO 嵌合体来修复突触功能和神经保护。合成了 4-甲基噻唑 (MZ) 衍生物，基于部分由 GABA A起作用的先导神经保护药效团受体增强。分析了 MZ 衍生物对初级神经元的保护作用，使其免受氧-葡萄糖剥夺和兴奋性毒性的影响。选定的神经保护衍生物被纳入 NO 嵌合体前药，创造了诺美噻唑。为了提供诺美噻唑药物类别的概念证明，对选定的例子进行了分析，以恢复 AD 转基因小鼠海马切片中的突触功能，逆转认知缺陷，以及前药及其神经保护性 MZ 代谢物的脑生物利用度。总之，分析数据表明这些嵌合诺美噻唑可用于治疗神经退行性疾病的多种成分，例如 AD。
• Modification of biologically active amides and amines with fluorine-containing heterocycles 8. γ-Carbolines modified with the 2-(2-trifluoromethylimidazo[1,2-a]pyridin-6-yl)ethyl fragment
  作者：V. B. Sokolov、A. Yu. Aksinenko、V. V. Grigoriev、S. O. Bachurin

  DOI：10.1007/s11172-013-0029-x

  日期：2013.1

  An approach to modification of biologically active g-carbolines with the 2-(2-trifluoromethylimidazo[1,2-a]pyridin-6-yl)ethyl fragment was proposed. The modification involves a reaction of 2-trifluoromethyl-6-vinylimidazo[1,2-a]pyridine with g-carbolines. The effect of the compounds obtained on neuronal NMDA receptors was studied by the radioligand binding method.

  提出了一种通过引入2-(2-三氟甲基咪唑并[1,2-a]吡啶-6-基)乙基片段来修饰生物活性γ-咔啉的方法。该修饰涉及2-三氟甲基-6-乙烯基咪唑并[1,2-a]吡啶与γ-咔啉的反应。利用放射性配体结合法研究了所得化合物对神经元NMDA受体的影响。
• COMPOUNDS AND METHODS FOR TREATMENT OF HYPERTENSION
  申请人：Medivation Technologies, Inc.

  公开号：US20150266884A1

  公开（公告）日：2015-09-24

  Hydrogenated pyrido[4,3-b]indoles, pyrido[3,4-b]indoles and azepino[4,5-b]indoles are described. The compounds may bind to and are adrenergic receptor α 2B antagonists. The compounds may also bind to and antagonize adrenergic receptor α 1B . The compounds may find use in therapy, e.g., to (i) reduce blood pressure and/or (ii) promote renal blood flow and/or (iii) decrease or inhibit sodium reabsorption. The compounds may also be used to treat diseases or conditions that are, or are expected to be, responsive to a decrease in blood pressure. Use of the compounds to treat cardiovascular and renal disorders is particularly described.

  氢化吡啶并[4,3-b]吲哚，吡啶[3,4-b]吲哚和氮杂七元[4,5-b]吲哚被描述。这些化合物可能与肾上腺素受体α2B结合并拮抗。这些化合物也可能与肾上腺素受体α1B结合并拮抗。这些化合物可能在治疗中发挥作用，例如（i）降低血压和/或（ii）促进肾脏血流和/或（iii）减少或抑制钠重吸收。这些化合物也可用于治疗对降低血压有反应或预期会有反应的疾病或症状。特别描述了使用这些化合物治疗心血管和肾脏疾病。