L-3-(2-(5-溴噻吩))丙氨酸 | 154593-58-5

• 物质功能分类: 生物化工 - 氨基酸及其衍生物 - 丙氨酸类衍生物
• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 中文名称: L-3-(2-(5-溴噻吩))丙氨酸
• 中文别名: L-2-(5-溴噻吩基)丙氨酸；L-2-(5-溴噻吩)丙氨酸
• 英文名称: (S)-2-amino-3-(5-bromothiophen-2-yl)propanoic acid
• 英文别名: (2S)-2-amino-3-(5-bromo-2-thienyl)propanoic acid；(2S)-2-Amino-3-(5-bromo-thiophen-2-yl)-propionic Acid；(2S)-amino-3-(5-bromo-thiophen-2-yl)-propionic acid；L-3-(5-bromo-thien-2-yl)alanine；(2S)-2-azaniumyl-3-(5-bromothiophen-2-yl)propanoate
• CAS: 154593-58-5
• 化学式: C₇H₈BrNO₂S
• 分子量: 250.116
• InChiKey: LKORPMMOJAJYLC-YFKPBYRVSA-N

物化性质

• 熔点：
  262 °C
• 沸点：
  368.5±42.0 °C(Predicted)
• 密度：
  1.747±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -0.7
• 重原子数：
  12
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  91.6
• 氢给体数：
  2
• 氢受体数：
  4

安全信息

• 危险性防范说明：
  P261,P305+P351+P338
• 危险性描述：
  H302,H315,H319,H335

SDS

Material Safety Data Sheet

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Section 1. Identification of the substance
Product Name: L-2-(5-Bromothienyl)alanine
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-2-(5-Bromothienyl)alanine
CAS number: 154593-58-5

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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.
Storage: Store in closed vessels, refrigerated.

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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
Melting point: No data
Flash point: No data
Density: No data
Molecular formula: C7H8BrNO2S
Molecular weight: 250.1

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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, hydrogen bromide, sulfur 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：

  L-3-(2-(5-溴噻吩))丙氨酸 在 焦碳酸二乙酯 、 三氟乙酸 作用下， 以 二氯甲烷 为溶剂， 反应 2.25h， 生成 (S)-2-[(S)-2-Amino-3-(5-bromo-thiophen-2-yl)-propionylamino]-3-(1H-imidazol-4-yl)-propionic acid methyl ester
  参考文献：
  名称：

  Studies on cyclic dipeptides, I: Aryl modifications ofcyclo-[Phe-His]

  摘要：

  Seven new cyclic dipeptides have been synthesized and tested for their applicability as tools to elucidate the mechanism of formation of mandelonitrile with (SS)-cyclo-[Phe-His] type catalysts. Conformational analyses based on H-1 NMR spectra are presented for all prepared cyclic dipeptides.

  DOI：

  10.1007/bf00807581
• 作为产物：
  描述：

  (2E)-3-(5-溴(2-噻吩))-2-丙烯酸 在 phenylalanine ammonia lyase from Anabaena variabilis 、 氨基甲酸铵 作用下， 以 水 为溶剂， 反应 4.0h， 以56 mg的产率得到L-3-(2-(5-溴噻吩))丙氨酸
  参考文献：
  名称：

  生物催化加氢胺化合成对映体纯环取代的 l-吡啶基丙氨酸

  摘要：

  目前获得含氮杂芳基丙氨酸的路线涉及复杂的多步合成，并且通常依赖于保护/脱保护步骤和浪费的色谱纯化。为了补充现有方法，开发了一种方便的伸缩策略，用于从相应的醛开始合成l-吡啶基丙氨酸类似物（12 个实例）和其他l-杂芳基丙氨酸（5 个实例）。来自Anabaena variabilis的苯丙氨酸解氨酶 (PAL)被用作生物催化剂，通过在必要时使用额外的去消旋化级联反应，转化率在 88% 到 95% 之间，分离产率为 32-60% 和完美的对映纯度 (>99% ee) .

  DOI：

  10.1021/acs.orglett.6b02559

文献信息

• Aryl and heteroaryl compounds, compositions, methods of use
  申请人：Mjalli M.M. Adnan

  公开号：US20050171148A1

  公开（公告）日：2005-08-04

  This invention provides aryl and heteroaryl compounds, methods of their preparation, pharmaceutical compositions comprising the compounds, and their use in treating human or animal disorders. The compounds of the invention may be useful as antagonists, or partial antagonist of factor IX and/or factor XI and thus, may be used to inhibit the intrinsic pathway of blood coagulation. The compounds may be useful in a variety of applications including the management, treatment and/or control of diseases caused in part by the intrinsic clotting pathway utilizing factor IX and/or XI.

  这项发明提供了芳基和杂环芳基化合物，以及它们的制备方法、包含这些化合物的药物组合物，以及它们在治疗人类或动物疾病中的应用。该发明的化合物可能用作因子IX和/或因子XI的拮抗剂或部分拮抗剂，因此可以用于抑制血液凝固的内在途径。这些化合物可能在多种应用中有用，包括利用因子IX和/或XI的内在凝血途径部分引起的疾病的管理、治疗和/或控制。
• [EN] NITRILE DERIVATIVE THAT ACTS AS INHIBITOR OF DIPEPTIDYL PEPTIDASE 1 AND USE THEREOF<br/>[FR] DÉRIVÉ DE NITRILE AGISSANT COMME INHIBITEUR DE LA DIPEPTIDYLE PEPTIDASE 1 ET SON UTILISATION<br/>[ZH] 一种作为二肽基肽酶1抑制剂的腈衍生物及其用途
  申请人：SICHUAN HAISCO PHARMACEUTICAL CO LTD

  公开号：WO2022042591A1

  公开（公告）日：2022-03-03

  提供一种式(I)所示的腈衍生物化合物、其立体异构体、氘代物、共晶、溶剂化物或药学上可接受的盐，其中各基团如说明书所定义。所述化合物具有二肽基肽酶1抑制活性，可用于制备治疗气道阻塞性疾病、支气管扩张、囊性纤维化、哮喘、肺气肿和慢性阻塞性肺病等疾病的药物。
• Thienylalanine derivatives as inhibitors of cell adhesion
  申请人：——

  公开号：US20030105080A1

  公开（公告）日：2003-06-05

  The present invention relates to compounds of formula (I), in which A, B, X, Y, R 1 , R 2 , R 3 and n have the meanings indicated in the claims. The compounds of formula (I) are valuable pharmacologically active compounds. They are vitronectin receptor antagonists and inhibitors of cell adhesion and are suitable for the therapy and prophylaxis of illnesses which are based on the interaction between vitronectin receptors and their ligands in cell-cell or cell-matrix interaction processes or which can be prevented, alleviated or cured by influencing such interactions. For example, they can be applied for inhibiting bone resorption by osteoclasts and thus for treating and preventing osteoporosis, or for inhibiting undesired angiogenesis or proliferation of cells of the vascular smooth musculature. The invention fruthermore relates to processes for the preparation of compounds of formula (I), their use, in particular as active ingredients in pharmaceuticals, and pharmaceutical compositions comprising them.

  本发明涉及式（I）的化合物，其中A、B、X、Y、R1、R2、R3和n具有所述索引中指示的含义。式（I）的化合物是有价值的药理活性化合物。它们是vitronectin受体拮抗剂和细胞黏附抑制剂，适用于基于细胞-细胞或细胞-基质相互作用过程中vitronectin受体和它们的配体之间相互作用的疾病的治疗和预防，或者可以通过影响这些相互作用来预防、缓解或治愈这些疾病。例如，它们可以应用于通过抑制骨吸收细胞破骨细胞来治疗和预防骨质疏松症，或者用于抑制不良血管生成或血管平滑肌细胞增殖。此外，本发明还涉及式（I）的化合物的制备过程，它们的使用，特别是作为药物中的活性成分，以及包含它们的药物组合物。
• Aryl and Heteroaryl Compounds, Compositions, Methods of Use
  申请人：Mjalli Adnan M.M.

  公开号：US20090124654A1

  公开（公告）日：2009-05-14

  This invention provides aryl and heteroaryl compounds of formula (X). The compounds of the invention may be useful as antagonists, or partial antagonist of factor IX and/or factor XI and thus, may be used to inhibit the intrinsic pathway of blood coagulation. Formula (X) wherein R 102 is selected from the group consisting of —C(O)OH, —C(O)OCH 3 , —C(O)O-t-butyl, —C(O)NH—OCH 2 -phenyl, C(O)NHOH, and —C(O)NHSO 2 CH 3 ; and wherein R 101 , R 103 , R 104 and Y are as defined herein.

  本发明提供了式（X）的芳基和杂芳基化合物。该发明的化合物可用作因子IX和/或因子XI的拮抗剂或部分拮抗剂，因此可用于抑制血液凝固的内在途径。式（X）中，R102选择自羧酸，甲氧基羰基，叔丁基氧羰基，氧化-苯基甲酰胺，氨基甲酰胺和磺酰甲基氨基甲酰胺等组成的群体；R101、R103、R104和Y的定义如本文所述。
• Aryl and heteroaryl compounds, compositions, and methods of use
  申请人：Mjalli M.M. Adnan

  公开号：US20070254916A1

  公开（公告）日：2007-11-01

  This invention provides aryl and heteroaryl compounds, methods of their preparation, pharmaceutical compositions comprising the compounds, and their use in treating human or animal disorders. The compounds of the invention may be useful as antagonists, or partial antagonist of factor IX and/or factor XI and thus, may be used to inhibit the intrinsic pathway of blood coagulation. The compounds may be useful in a variety of applications including the management, treatment and/or control of diseases caused in part by the intrinsic clotting pathway utilizing factor IX and/or XI.

  本发明提供了芳基和杂环芳基化合物，其制备方法，包含这些化合物的制药组合物以及它们在治疗人类或动物疾病中的应用。该发明的化合物可能作为因子IX和/或因子XI的拮抗剂或部分拮抗剂而有用，因此可以用于抑制血液凝固的内在途径。这些化合物可以用于各种应用，包括利用因子IX和/或XI的内在凝血途径引起的疾病的管理、治疗和/或控制。