2-氨基-3-氰基-4,7-二氢噻吩并-[2,3-c]吡啶-6(5H)-羧酸叔丁酯 | 150986-83-7

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 噻吩并吡啶类
• 中文名称: 2-氨基-3-氰基-4,7-二氢噻吩并-[2,3-c]吡啶-6(5H)-羧酸叔丁酯
• 英文名称: 2-amino-3-cyano-4,7-dihydro-5H-thieno[2,3-c]pyridine-6-carboxylic acid tert-butyl ester
• 英文别名: tert-butyl 2-amino-3-cyano-4,5-dihydrothieno[2,3-c]pyridine-6(7H)-carboxylate；tert-butyl 2-amino-3-cyano-4,7-dihydrothieno[2,3-c]pyridine-6(5H)-carboxylate；2-amino-3-cyano-4,7-dihydro-thieno[2,3-c]pyridine-6(5H)-carboxylic acid 1,1-dimethylethyl ester；2-Amino-3-Cyano-4,5,6,7-tetrahydro-5H-thieno[2,3-c]pyridine-6-carboxylic acid tert-butyl ester；2-amino-3-cyano-4,7-dihydro-5H-thieno[2,3-c]pyridine-6-carboxylic acid tertbutyl ester；tert-butyl 2-amino-3-cyano-5,7-dihydro-4H-thieno[2,3-c]pyridine-6-carboxylate
• CAS: 150986-83-7
• 化学式: C₁₃H₁₇N₃O₂S
• mdl: MFCD05664037
• 分子量: 279.363
• InChiKey: HFWVFBQVIXKINU-UHFFFAOYSA-N

物化性质

• 熔点：
  193-195°C
• 沸点：
  475.8±45.0 °C(Predicted)
• 密度：
  1.29±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  19
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.538
• 拓扑面积：
  108
• 氢给体数：
  1
• 氢受体数：
  5

安全信息

• 危险等级：
  IRRITANT
• 危险品标志：
  Xi
• 海关编码：
  2934999090

SDS

Material Safety Data Sheet

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Section 1. Identification of the substance
Product Name: tert-Butyl 2-amino-3-cyano-4,7-dihydrothieno[2,3-c]pyridine-6(5h)-carboxylate
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: tert-Butyl 2-amino-3-cyano-4,7-dihydrothieno[2,3-c]pyridine-6(5h)-carboxylate
CAS number: 150986-83-7

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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: C13H17N3O2S
Molecular weight: 279.4

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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, 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：

  2-氨基-3-氰基-4,7-二氢噻吩并-[2,3-c]吡啶-6(5H)-羧酸叔丁酯 在 N,N'-羰基二咪唑 、 三乙胺 作用下， 以 二氯甲烷 为溶剂， 生成 3-cyano-2-[3-(2-methoxy-phenyl)-propanoylamino]-4,7-dihydro-5H-thieno[2,3-c]pyridine-6-carboxylic acid tert-butyl ester
  参考文献：
  名称：

  WO2008/20024

  摘要：

  公开号：
• 作为产物：
  描述：

  4-氧代哌啶酮盐酸盐 在 吗啉 、 1,4-二氧六环 、 sulfur 、 三乙胺 作用下， 以 乙醇 、 水 为溶剂， 反应 2.0h， 生成 2-氨基-3-氰基-4,7-二氢噻吩并-[2,3-c]吡啶-6(5H)-羧酸叔丁酯
  参考文献：
  名称：

  Structure–activity relationships of new cyanothiophene inhibitors of the essential peptidoglycan biosynthesis enzyme MurF

  摘要：

  Peptidoglycan is an essential component of the bacterial cell wall, and enzymes involved in its biosynthesis represent validated targets for antibacterial drug discovery. MurF catalyzes the final intracellular peptidoglycan biosynthesis step: the addition of D-Ala-D-Ala to the nucleotide precursor UDP-MurNAc-L-Ala-gamma-D-Glu-meso-DAP (or L-Lys). As MurF has no human counterpart, it represents an attractive target for the development of new antibacterial drugs. Using recently published cyanothiophene inhibitors of MurF from Streptococcus pneumoniae as a starting point, we designed and synthesized a series of structurally related derivatives and investigated their inhibition of MurF enzymes from different bacterial species. Systematic structural modifications of the parent compounds resulted in a series of nanomolar inhibitors of MurF from S. pneumoniae and micromolar inhibitors of MurF from Escherichia coli and Staphylococcus aureus. Some of the inhibitors also show antibacterial activity against S. pneumoniae R6. These findings, together with two new co-crystal structures, represent an excellent starting point for further optimization toward effective novel antibacterials. (C) 2013 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2013.05.013

文献信息

• [EN] COMPOUNDS FOR TREATING VIRAL INFECTIONS<br/>[FR] COMPOSÉS POUR TRAITER DES INFECTIONS VIRALES
  申请人：PASTEUR INSTITUT KOREA

  公开号：WO2015158908A1

  公开（公告）日：2015-10-22

  The present invention relates to small molecule compounds and their use in the treatment of diseases, in particular viral diseases, in particular hepatitis C virus (HCV).

  本发明涉及小分子化合物及其在治疗疾病中的应用，特别是病毒性疾病，尤其是丙型肝炎病毒（HCV）。
• Novel tetrahydrobenzo[b]thiophen-2-yl)urea derivatives as novel α-glucosidase inhibitors: Synthesis, kinetics study, molecular docking, and in vivo anti-hyperglycemic evaluation
  作者：Hong-Xu Xie、Juan Zhang、Yue Li、Jin-He Zhang、Shan-Kui Liu、Jie Zhang、Hua Zheng、Gui-Zhou Hao、Kong-Kai Zhu、Cheng-Shi Jiang

  DOI：10.1016/j.bioorg.2021.105236

  日期：2021.10

  α-Glucosidase inhibitors, which can inhibit the digestion of carbohydrates into glucose, are one of important groups of anti-type 2 diabetic drugs. In the present study, we report our effort on the discovery and optimization of α-glucosidase inhibitors with tetrahydrobenzo[b]thiophen-2-yl)urea core. Screening of an in-house library revealed a moderated α-glucosidase inhibitors, 5a, and then the following

  α-葡萄糖苷酶抑制剂是一类重要的抗2型糖尿病药物，可抑制碳水化合物消化为葡萄糖。在本研究中，我们报告了我们在发现和优化具有四氢苯并[ b ]噻吩-2-基)脲核心的α-葡萄糖苷酶抑制剂方面的努力。内部文库的筛选揭示了一种缓和的 α-葡萄糖苷酶抑制剂，5a，然后进行以下结构优化以获得更有效的衍生物。与亲本化合物5a (IC 50为 26.71 ± 1.80 μM) 和阳性对照阿卡波糖 (IC 50为 258.53 ± 1.27 μM)相比，大多数这些衍生物对 α-葡萄糖苷酶的抑制活性增加。其中，化合物8r (IC 50  = 0.59 ± 0.02 μM) 和8s (IC 50  = 0.65 ± 0.03 μM) 是最有效的抑制剂，并且表现出优于 α-淀粉酶的选择性。荧光猝灭实验证实了两种化合物与α-葡萄糖苷酶的直接结合。动力学研究表明，这些化合物是非竞争性抑制剂，这与分子对接结果一致，即化
• Discovery of Selective Phosphodiesterase 1 Inhibitors with Memory Enhancing Properties
  作者：Brian Dyck、Bryan Branstetter、Tawfik Gharbaoui、Andrew R. Hudson、J. Guy Breitenbucher、Laurent Gomez、Iriny Botrous、Tami Marrone、Richard Barido、Charles K. Allerston、E. Peder Cedervall、Rui Xu、Vandana Sridhar、Ryan Barker、Kathleen Aertgeerts、Kara Schmelzer、David Neul、Dong Lee、Mark Eben Massari、Carsten B. Andersen、Kristen Sebring、Xianbo Zhou、Robert Petroski、James Limberis、Martin Augustin、Lawrence E. Chun、Thomas E. Edwards、Marco Peters、Ali Tabatabaei

  DOI：10.1021/acs.jmedchem.7b00302

  日期：2017.4.27

  A series of potent thienotriazolopyrimidinone-based PDE1 inhibitors was discovered. X-ray crystal structures of example compounds from this series in complex with the catalytic domain of PDE1B and PDE10A were determined, allowing optimization of PDE1B potency and PDE selectivity. Reduction of hERG affinity led to greater than a 3000-fold selectivity for PDE1B over hERG. 6-(4-Methoxybenzyl)-9-((tet

  发现了一系列基于硫杂三氮杂吡喃二酮的有效PDE1抑制剂。确定了该系列示例化合物与PDE1B和PDE10A催化结构域复合的X射线晶体结构，从而优化了PDE1B的效力和PDE的选择性。hERG亲和力的降低导致对PDE1B的选择性是hERG的3000倍以上。6-（4-甲氧基苄基）-9-（（（四氢-2 H-吡喃-4-基）甲基）-8,9,10,11-四氢吡啶基[4'，3'：4,5]噻吩并[3， 2- e ] [1,2,4]三唑并[1,5- c ]嘧啶-5（6 H）-1被确定为口服生物可利用的且可穿透脑的PDE1B酶抑制剂，在大鼠模型中具有有效的记忆增强作用对象识别存储器。
• Novel Tetrahydropyridothiophenes
  申请人：Pekari Klaus

  公开号：US20080260749A1

  公开（公告）日：2008-10-23

  Compounds of a certain formula (I) in which Ra and Rb have the meanings indicated in the description, are novel effective compounds with anti-proliferative and apoptosis inducing activity.

  具有某种化学式（I）的化合物，在其中Ra和Rb具有描述中指示的含义，是具有抗增殖和诱导凋亡活性的新型有效化合物。
• Novel substituted 3-cyanothiophene acetamides as glucagon receptor antagonists
  申请人：——

  公开号：US20040209943A1

  公开（公告）日：2004-10-21

  The present invention relates to compounds of formula (I) 1 wherein R1, R2, R3, R4 and n are as defined in the description and claims, and pharmaceutically acceptable salts thereof. The compounds are useful for the treatment and/or prophylaxis of diseases which are associated with the antagonism of the glucagon receptor, such as diabetes.

  本发明涉及式(I)1的化合物，其中R1、R2、R3、R4和n如描述和索赔中所定义，并且其药学上可接受的盐。这些化合物对于治疗和/或预防与胰高血糖素受体拮抗有关的疾病，如糖尿病，是有用的。