2-氨基-5,6-二氢-环戊烷并噻吩-3-羰酰胺 | 77651-38-8

• 物质功能分类: 医药中间体 - 杂环化合物 - 噻吩类化合物
• 分子结构分类: 有机化合物 - 有机杂环化合物 - 噻吩类
• 中文名称: 2-氨基-5,6-二氢-环戊烷并噻吩-3-羰酰胺
• 中文别名: 2-氨基-5,6-二氢-4H-环戊烯并噻吩-3-甲酰胺；2-氨基-5,6-二氢-4H-环五[B]噻吩-3-羧基酸酰胺
• 英文名称: 2-amino-5,6-dihydro-4H-cyclopenta[b]thiophene-3-carboxamide
• CAS: 77651-38-8
• 化学式: C₈H₁₀N₂OS
• mdl: MFCD00122463
• 分子量: 182.246
• InChiKey: CIYGFKXNRTYHLB-UHFFFAOYSA-N

物化性质

• 熔点：
  169-171℃
• 沸点：
  308.2±42.0 °C(Predicted)
• 密度：
  1.412

计算性质

• 辛醇/水分配系数(LogP)：
  1.4
• 重原子数：
  12
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.375
• 拓扑面积：
  97.4
• 氢给体数：
  2
• 氢受体数：
  3

安全信息

• 危险等级：
  IRRITANT
• 危险品标志：
  Xi
• 安全说明：
  S26,S36/37/39
• 危险类别码：
  R22,R36/37/38
• 海关编码：
  2934999090
• 危险性防范说明：
  P261,P305+P351+P338
• 危险性描述：
  H315,H319,H335
• 储存条件：
  2-8℃

SDS

Material Safety Data Sheet

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Section 1. Identification of the substance
Product Name: 2-Amino-4H,5H,6H-cyclopenta[b]thiophene-3-carboxamide
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: 2-Amino-4H,5H,6H-cyclopenta[b]thiophene-3-carboxamide
CAS number: 77651-38-8

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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: C8H10N2OS
Molecular weight: 182.2

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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, 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-5,6-二氢-环戊烷并噻吩-3-羰酰胺 在 溶剂黄146 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 8.0h， 生成
  参考文献：
  名称：

  2-Imino-2H-1-benzopyrans 与亲核试剂的再循环 - 2-Iminocoumarin-3-carboxamides 与 2-Aminothiophene-3-carboxamides 的反应

  摘要：

  在我们合成香豆素的研究过程中，研究了 2-亚氨基香豆素-3-羧酰胺与一系列 2-氨基噻吩-3-羧酰胺的相互作用。已确定初始产物 - 2-取代香豆素-3-羧酰胺 - 通过在 DMF 中回流可以重排为 2-(香豆素-3-基)噻吩并[2,3-d]嘧啶-4-酮。

  DOI：

  10.1055/s-2006-926333
• 作为产物：
  描述：

  2-氨基-5,6-二氢-4H-环戊烯并噻吩-3-甲腈 在 PPA 、 磷酸 作用下， 反应 5.0h， 以25%的产率得到2-氨基-5,6-二氢-环戊烷并噻吩-3-羰酰胺
  参考文献：
  名称：

  双环1,2,6-噻二嗪的合成

  摘要：

  来自吡咯、呋喃和噻吩系列的α-氨基酸酰胺转化为新的硫杂环。正在研究这些化合物的稳定性。

  DOI：

  10.1002/ardp.19813140213

文献信息

• 2-(3,4-Dihydro-4-Oxothieno[2,3-d]pyrimidin-2-ylthio) Acetamides as a New Class of Falcipain-2 Inhibitors. 3. Design, Synthesis and Biological Evaluation
  作者：Jin Zhu、Tong Chen、Jie Liu、Ruoqun Ma、Weiqiang Lu、Jin Huang、Honglin Li、Jian Li、Hualiang Jiang

  DOI：10.3390/molecules14020785

  日期：——

  The cysteine protease falcipain-2 (FP-2) of Plasmodium falciparum is a principal cysteine protease and an essential hemoglobinase of erythrocytic P. falciparum trophozoites, making it become an attractive target enzyme for developing anti-malarial drugs. In this study, a series of novel small molecule FP-2 inhibitors have been designed and synthesized based on compound 1, which was identified by using structure-based virtual screening in conjunction with an enzyme inhibition assay. All compounds showed high inhibitory effect against FP-2 with IC50s of 1.46-11.38 μM, and the inhibitory activity of compound 2a was ~2 times greater than that of prototype compound 1. The preliminary SARs are summarized and should be helpful for future inhibitor design, and the novel scaffold presented here, with its potent inhibitory activity against FP-2, also has potential application in discovery of new anti-malarial drugs.

  恶性疟原虫 (Plasmodium falciparum) 半胱氨酸蛋白酶 (falcipain-2， FP-2) 是原生质型疟原虫的主要半胱氨酸蛋白酶和必须的血红蛋白酶，这使得它成为研制抗疟药物的一个有吸引力的靶标酶。在本研究中，我们基于用酶抑制法结合基于结构的虚拟筛选得到的化合物 1，设计并合成了系列新型小分子 FP-2 抑制剂。所有化合物均为 FP-2的高效抑制剂，其半抑制浓度 (IC50) 值范围为 1.46 至 11.38 μM，化合物 2a 的抑制活性是母体化合物 1 的 2倍左右。本研究概括总结的初步构效关系将有助于未来抑制剂的设计，这里展示的新骨架以其对 FP-2的强效抑制活性，在发现新型抗疟药物方面也具有潜在的应用价值。
• Structure–activity relationships for inhibitors of Pseudomonas aeruginosa exoenzyme S ADP-ribosyltransferase activity
  作者：Michael Saleeb、Charlotta Sundin、Öznur Aglar、Ana Filipa Pinto、Mahsa Ebrahimi、Åke Forsberg、Herwig Schüler、Mikael Elofsson

  DOI：10.1016/j.ejmech.2017.11.036

  日期：2018.1

  recombinant ExoS ADPRT domain. Herein, we report structure–activity relationships of this compound class by comparing a total of 51 compounds based on a thieno [2,3-d]pyrimidin-4(3H)-one and 4-oxo-3,4-dihydroquinazoline scaffolds. Improved inhibitors with in vitro IC50 values of 6 μM were identified. Importantly, we demonstrated that the most potent inhibitors block ADPRT activity of native full-length

  在感染期间，革兰氏阴性机会性病原体铜绿假单胞菌利用其III型分泌系统将毒素外切酶S（ExoS）转移到真核宿主细胞的细胞质中。ExoS是一种必不可少的体内毒力因子，可使铜绿假单胞菌避免吞噬作用并最终杀死宿主细胞。ExoS主要通过ADP-核糖基转移酶（ADPRT）活性引起其致病性。我们最近鉴定了具有体外IC 50的新型ExoS ADPRT抑制剂使用重组ExoS ADPRT结构域进行酶促测定时，大约20μM的核酸。在这里，我们通过比较基于噻吩并[2,3- d ]嘧啶-4（3 H）-one和4-oxo-3,4-dihydroquinazoline支架的51种化合物来报告该化合物类别的结构-活性关系。鉴定出体外IC 50值为6μM的改良抑制剂。重要的是，我们证明了最有效的抑制剂在酶促试验中能阻断铜绿假单胞菌分泌的天然全长ExoS的ADPRT活性，IC 50值为1.3μM 。该化合物类别有望成为开发新型抗菌剂的起点。
• Exploiting Drug-Resistant Enzymes as Tools To Identify Thienopyrimidinone Inhibitors of Human Immunodeficiency Virus Reverse Transcriptase-Associated Ribonuclease H
  作者：Takashi Masaoka、Suhman Chung、Pierluigi Caboni、Jason W. Rausch、Jennifer A. Wilson、Humeyra Taskent-Sezgin、John A. Beutler、Graziella Tocco、Stuart F. J. Le Grice

  DOI：10.1021/jm400405z

  日期：2013.7.11

  The thienopyrimidinone 5,6-dimethyl-2-(4-nitrophenyl)thieno[2,3-d]pyrimidin-4(3H)-one (DNTP) occupies the interface between the p66 ribonuclease H (RNase H) domain and p51 thumb of human immunodeficiency virus reverse transcriptase (HIV RT), thereby inducing a conformational change incompatible with catalysis. Here, we combined biochemical characterization of 39 DNTP derivatives with antiviral testing

  噻吩并嘧啶酮5,6-二甲基-2-(4-硝基苯基)噻吩并[2,3 - d ]嘧啶-4(3 H)-one (DNTP) 占据 p66 核糖核酸酶 H (RNase H) 域和人类免疫缺陷病毒逆转录酶 (HIV RT) 的 p51 拇指之间的界面，从而导致与催化不相容的构象变化。在这里，我们将 39 种 DNTP 衍生物的生化表征与所选化合物的抗病毒测试相结合。除了野生型 HIV-1 RT，还使用合理设计的 p66/p51 异二聚体对衍生物进行了评估，这些异二聚体表现出高水平的 DNTP 敏感性或抗性。该策略鉴定了 3',4'-二羟基苯基（儿茶酚）取代的噻吩并嘧啶酮，对野生型 HIV-1 RT 和耐药变体具有亚微摩尔的体外活性。热位移分析表明，与活性位点 RNase H 抑制剂相比，这些噻吩并嘧啶酮会破坏稳定酶，在某些情况下将T m降低 5 °C。重要的是，含有儿茶酚的噻吩并嘧啶酮还抑制细胞中的
• Cyclopentathiophene/cyclohexathiophene DNA methyltransferase inhibitors
  申请人：Vankayalapati Hariprasad

  公开号：US20100222381A1

  公开（公告）日：2010-09-02

  Compounds represented by Formula (I): are useful in treating diseases, such as cancer, that are mediated and/or associated (at least in part) with DNMT3b activity. The compounds can be formulated as pharmaceutically acceptable compositions for administration to a subject in need thereof.

  由式（I）表示的化合物在治疗疾病方面很有用，例如癌症，这些疾病与DNMT3b活性有关。这些化合物可以制备成药学上可接受的组合物，用于向需要的受试者施用。
• [EN] SMALL MOLECULE REGULATORS OF MITOCHONDRIAL FUSION AND METHODS OF USE THEREOF<br/>[FR] RÉGULATEURS DE TYPE PETITE MOLÉCULE DE FUSION MITOCHONDRIALE ET PROCÉDÉS D'UTILISATION DE CEUX-CI
  申请人：UNIV WASHINGTON

  公开号：WO2018200323A1

  公开（公告）日：2018-11-01

  Compositions comprising small molecule mitofusin agonists are described. The mitofusin modulating agents are useful for treating diseases or disorders associated with a mitochondria-associated disease, disorder, or condition such as diseases or disorders associated with mitofusin 1 (Mfn1) and/or mitofusin 2 (Mfn2), or mitochondrial dysfunction. Methods of treatment, pharmaceutical formulations, and screening methods for identifying compounds that regulate mitochondrial function are also described.

  描述了包含小分子线粒体融合蛋白激动剂的组合物。这些线粒体融合蛋白调节剂对于治疗与线粒体相关疾病、紊乱或状况有关的疾病或紊乱非常有用，例如与线粒体融合蛋白1（Mfn1）和/或线粒体融合蛋白2（Mfn2）有关的疾病或紊乱，或线粒体功能障碍。还描述了治疗方法、药物配方以及用于识别调节线粒体功能的化合物的筛选方法。