(S)-2,3,4,9-四氢-1H-吡啶[3,4-b]吲哚-3-羧酸 | 42438-90-4

• 物质功能分类: 医药中间体 - 杂环化合物 - 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: (S)-2,3,4,9-四氢-1H-吡啶[3,4-b]吲哚-3-羧酸
• 中文别名: L-1,2,3,4-四氢正哈尔满碱-3-羧酸；(S)-2,3,4,9-四氢-1H-吡啶并[3,4-B]吲哚-3-羧酸；(S)-2,3,4,9-四氢-1H-吡啶[3,4-B]吲哚-3-羧酸
• 英文名称: 3-carboxy-1,2,3,4-tetrahydro-2-carboline
• 英文别名: 3S-1,2,3,4-tetrahydro-β-carboline-3-carboxylic acid；(3S)-tetrahydro-β-carboline-3-carboxylic acid；(3S)-2,3,4,9-tetrahydro-1H-pyrido[3,4-b]indol-2-ium-3-carboxylate
• CAS: 42438-90-4
• 化学式: C₁₂H₁₂N₂O₂
• mdl: MFCD00272641
• 分子量: 216.239
• InChiKey: FSNCEEGOMTYXKY-JTQLQIEISA-N

物化性质

• 熔点：
  289 °C (dec.)(lit.)
• 沸点：
  485.0±45.0 °C(Predicted)
• 密度：
  1.377±0.06 g/cm3(Predicted)
• 溶解度：
  可溶1.5mg/mL，澄清（溶剂：0.1N HCl:DMSO (1:1)；温热）
• 稳定性/保质期：
  常规情况下不会分解，没有危险反应。

计算性质

• 辛醇/水分配系数(LogP)：
  -1.2
• 重原子数：
  16
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  65.1
• 氢给体数：
  3
• 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
• WGK Germany：
  3
• 海关编码：
  2933990090
• 安全说明：
  S26,S36
• 危险性防范说明：
  P233,P260,P261,P264,P271,P280,P302+P352,P304,P304+P340,P305+P351+P338,P312,P321,P332+P313,P337+P313,P340,P362,P403,P403+P233,P405,P501
• 危险性描述：
  H315,H319,H335
• 储存条件：
  密封，在2°C至-8°C之间保存。

SDS

Material Safety Data Sheet

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Section 1. Identification of the substance
Product Name: L-1,2,3,4-Tetrahydronorharman-3-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: L-1,2,3,4-Tetrahydronorharman-3-carboxylic acid
CAS number: 42438-90-4

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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: C12H12N2O2
Molecular weight: 216.2

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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

制备方法与用途

(S)-2,3,4,9-四氢-1H-吡啶[3,4-B]吲哚-3-羧酸是一种吲哚类杂环化合物，主要应用于实验室研发过程中。

反应信息

• 作为反应物：
  描述：

  (S)-2,3,4,9-四氢-1H-吡啶[3,4-b]吲哚-3-羧酸 在 sodium tetrahydroborate 、 硫酸 作用下， 以 四氢呋喃 、 甲醇 为溶剂， 反应 36.0h， 生成 3S-1,2,3,4-tetrahydro-β-carboline-3-ol
  参考文献：
  名称：

  新型多功能抗坏血酸三唑衍生物，用于淀粉样蛋白途径抑制，抗炎和神经保护

  摘要：

  阿尔茨海默氏病（AD）是一种常见的神经退行性疾病。到2050年，患有AD的患者人数预计将达到1.52亿。多奈哌齐，卡巴拉汀，加兰他敏和美金刚是目前美国食品和药物管理局批准用于AD治疗的仅有的四种药物。但是，这些药物只能缓解AD症状。因此，本研究着重于发现具有与淀粉样蛋白级联有关的AD病因学的多靶点调控的新型先导化合物。由于多种特性，包括抗氧化剂活性，淀粉样蛋白聚集抑制以及被转运到大脑和神经元的能力，抗坏血酸结构已被指定为核心功能域。通过铜（I）催化的叠氮化物-炔烃环加成反应（点击化学反应）合成了多功能抗坏血酸衍生物。体外和基于细胞的测定表明，化合物2c和5c作为β-分泌酶1抑制剂，淀粉样蛋白聚集抑制剂以及抗氧化剂，神经保护剂和抗炎剂，表现出突出的多功能活性。在纳摩尔水平相当低的浓度下，观察到促进神经保护和抗发炎的活性发生了显着变化。此外，计算机模拟研究表明，化合物2c和5c能够被钠依赖性维生素C转运蛋白2穿过血脑屏障。

  DOI：

  10.3390/molecules26061562
• 作为产物：
  描述：

  9-(tert-butyl) 3-methyl (S)-1,2,3,4-tetrahydro-9H-pyrido[3,4-b]indole-3,9-dicarboxylate 在 盐酸 、 水 、 lithium hydroxide 作用下， 以 四氢呋喃 、 1,4-二氧六环 、 甲醇 为溶剂， 反应 8.0h， 生成 (S)-2,3,4,9-四氢-1H-吡啶[3,4-b]吲哚-3-羧酸
  参考文献：
  名称：

  （R / S）-BINOL-α-磷酸乙内酰胺氨基甲酸酯和（R / S）-钛（IV）双酚酸酯-催化的对映选择性分子内Heck / Aza-Diels-Alder环加成（IHADA）：一种简便的方法

  摘要：

  的（R / S） -钛（IV）BINOLate催化对映选择性高分子内的Heck /氮杂狄尔斯-阿尔德环加成（IHADA）级联的开发是为了从制备tetrahydropyridoindoles（THPS）和octahydropyrazinopyridoindoles（oHPPs）原位生成的（- [R /小号一锅中的BINOLα-磷酰氧基氨基甲酸酯（αPPC2）。观察到（R / S）-αPPC2与（R / S）-钛（IV）BINOLate之间的手性协同作用，并成功地用于构建各种t​​HP（7个实例）和oHPP（17个实例）。

  DOI：

  10.1002/adsc.201300522

文献信息

• PAR4 AGONIST PEPTIDES
  申请人：Bristol-Myers Squibb Company

  公开号：US20130289238A1

  公开（公告）日：2013-10-31

  The present invention provides PAR4 agonist peptides. These peptides are useful for developing robust PAR4 receptor assays.

  本发明提供PAR4激动肽。这些肽对于开发强大的PAR4受体测定方法非常有用。
• A new class of anti-thrombosis hexahydropyrazino-[1′,2′:1,6]pyrido-[3,4-b]-indole-1,4-dions: Design, synthesis, logK determination, and QSAR analysis
  作者：Jiawang Liu、Guofeng Wu、Guohui Cui、Wei-Xuan Wang、Ming Zhao、Chao Wang、Ziding Zhang、Shiqi Peng

  DOI：10.1016/j.bmc.2007.06.012

  日期：2007.9.1

  (tetrahydro-beta-carboline-3-carboxy-l-amino acid benzylesters, 2-aminoacyltetrahydro-beta-carboline-3-carboxylic acid benzylesters) were prepared and used for the cyclization to form 5a-t. Coupling hydrochloric acid salt of tetrahydro-beta-carboline-3-carboxylic acid esters and Boc-amino acids in the reported literature usually generates very low yield products accompanied by racemization. However, in our case, the

  基于N-[（3S）]-1,2,3,4-四氢-β-咔啉-3-羧基] -1-赖氨酸在乙酸水溶液（5％）和大鼠中的环化血浆给出了相同的产物，并假设环化产物具有抗血栓活性，我们报道了20种六氢吡嗪并[1'，2'：1,6]吡啶并[ 3,4-b]吲哚-1,4-dion（5a-t）作为潜在的抗血栓形成剂。制备了两种中间体（四氢-β-咔啉-3-羧基-1-氨基酸苄酯，2-氨基酰基四氢-β-咔啉-3-羧酸苄酯），并用于环化形成5a-t。在已报道的文献中，四氢-β-咔啉-3-羧酸酯的盐酸盐与Boc-氨基酸的偶联通常产生非常低的收率产物，并伴随着消旋作用。然而，在我们的情况下，四氢-β-咔啉-3-羧酸苄酯的游离碱以高收率且没有外消旋作用产生了所需的产物。来自体外和体内研究的抗血栓形成结果表明，5a-t可能是一类新型的抗血栓形成剂，口服有效有效浓度为0.5μmol/ kg。此外，使用e-dragon服务器生成的分子
• Carboline-3-carboxylic acid modified related sequences of Ala-Arg-Pro-Ala-Lys, their synthesis and use as thromobolytic agent
  申请人：Peng Shiqi

  公开号：US20050080015A1

  公开（公告）日：2005-04-14

  The present invention relates to the protected intermediates and the deprotected products of P6A, related to the protected pseudopeptides introducing the protected intermediateds of P6A to 3S-(2-Boc)-1,2,3,4-tetrahydro-β-carboline-3-carboxylic acid and the deprotected pseudopeptides, related to the protected pseudopeptides introducing the protected intermediateds of P6A to 3S-1,2,3,4-tetrahydro-β-carboline-3-carboxylic acid benzyl ester, related to the methods for their preparation, and related to their use as the thrombolytic agents.

  本发明涉及P6A的保护中间体和去保护产物，涉及将P6A的保护伪肽引入到3S-(2-Boc)-1,2,3,4-四氢-β-咔啉-3-羧酸的保护中间体和去保护伪肽，涉及将P6A的保护伪肽引入到3S-1,2,3,4-四氢-β-咔啉-3-羧酸苄酯的保护中间体，涉及它们的制备方法，以及它们作为溶栓剂的用途。
• PhI(OAc)₂-mediated one-pot oxidative decarboxylation and aromatization of tetrahydro-β-carbolines: synthesis of norharmane, harmane, eudistomin U and eudistomin I
  作者：Ahmed Kamal、Yellaiah Tangella、Kesari Lakshmi Manasa、Manda Sathish、Vunnam Srinivasulu、Jadala Chetna、Abdullah Alarifi

  DOI：10.1039/c5ob00871a

  日期：——

  A new strategy for synthesis of β-carbolines via one-pot oxidative decarboxylation at room temperature is developed for the first time.

  首次开发了一种在室温下通过一锅法氧化脱羧合成β-咔啉的新策略。

• Design and synthesis of β-carboline derivatives with nitrogen mustard moieties against breast cancer
  作者：Jianan Sun、Jiesen Wang、Xinyan Wang、Xu Hu、Hao Cao、Jiao Bai、Dahong Li、Huiming Hua

  DOI：10.1016/j.bmc.2021.116341

  日期：2021.9

  To discover the promising antitumor agents, a series of β-carboline derivatives with nitrogen mustard moieties were designed and synthesized. Most target derivatives showed antiproliferative activity against MCF-7 and MDA-MB-231 cells. Among them, (1-methyl-9H-pyrido[3,4-b]indol-3-yl)methyl (S)-3-(4-(bis(2-chloroethyl)amino)phenyl)-2-formamidopropanoate possessed the most potent antiproliferative activity

  为了发现有前景的抗肿瘤剂，设计并合成了一系列具有氮芥部分的β-咔啉衍生物。大多数目标衍生物对 MCF-7 和 MDA-MB-231 细胞显示出抗增殖活性。其中，（1-甲基-9- ħ -吡啶并[3,4- b ]吲哚-3-基）甲基（小号）-3-（4-（双（2-氯乙基）氨基）苯基）-2- formamidopropanoate具有最强的抗增殖活性，IC 50值分别为 1.79 μM 和 4.96 μM，显着高于母体化合物，功效与阳性对照阿霉素相当。更重要的是，它对人正常乳腺细胞系 MCF-10A（IC50  > 20 μM)，表现出一定的选择性。随后，进一步的机制探索表明它在MDA-MB-231细胞中诱导了G2/M期细胞周期阻滞和凋亡。DCFH-DA 荧光探针试验和彗星试验表明，该化合物可导致细胞内 ROS 积累和 DNA 损伤。此外，它在体外对MDA-MB-231细胞的迁移、侵袭和粘附发挥了强效抑制作用。简而言之，(1-甲基-9