5,6,7,8-四氢苯并[4,5]噻吩并[2,3-d]嘧啶-4-胺 | 4994-88-1

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 噻吩并嘧啶酮衍生物
• 中文名称: 5,6,7,8-四氢苯并[4,5]噻吩并[2,3-d]嘧啶-4-胺
• 中文别名: 5,6,7,8-四氢[1]苯并噻吩[2,3-D]嘧啶-4-胺
• 英文名称: 5,6,7,8-tetrahydrobenzo[b]thiopheno[2,3-d]pyrimidin-4-ylamine
• 英文别名: 5,6,7,8-tetrahydrobenzo[4,5]thieno[2,3-d]pyrimidin-4-amine；4-amino-5,6,7,8-tetrahydrobenzothieno-[2,3-d]-pyrimidine；4-amino-5,6,7,8-tetrahydrobenzothieno[3,2-d]pyrimidine；4-amino-5,6,7,8-tetrahydrobenzo[b]thiopheno[2,3-d]pyrimidine；5,6,7,8-tetrahydro-benzo[4,5]thieno[2,3-d]pyrimidin-4-ylamine；5,6,7,8-Tetrahydro[1]benzothieno[2,3-d]pyrimidin-4-amine；5,6,7,8-tetrahydro-[1]benzothiolo[2,3-d]pyrimidin-4-amine
• CAS: 4994-88-1
• 化学式: C₁₀H₁₁N₃S
• mdl: MFCD00203885
• 分子量: 205.283
• InChiKey: QXPQVUQBEBHHQP-UHFFFAOYSA-N

物化性质

• 熔点：
  265 °C(Solv: N,N-dimethylformamide (68-12-2))
• 沸点：
  424.9±40.0 °C(Predicted)
• 密度：
  1.381±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  14
• 可旋转键数：
  0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  80
• 氢给体数：
  1
• 氢受体数：
  4

安全信息

• 海关编码：
  2934999090

SDS

Material Safety Data Sheet

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Section 1. Identification of the substance
Product Name: 5,6,7,8-Tetrahydro-benzo[4,5]thieno[2,3-d]pyrimidin-4-ylamine
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: 5,6,7,8-Tetrahydro-benzo[4,5]thieno[2,3-d]pyrimidin-4-ylamine
CAS number: 4994-88-1

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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: C10H11N3S
Molecular weight: 205.3

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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, 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：

  5,6,7,8-四氢苯并[4,5]噻吩并[2,3-d]嘧啶-4-胺 在 二溴甲烷 、 亚硝酸异戊酯 作用下， 反应 1.0h， 以26%的产率得到4-Bromo-5,6,7,8-tetrahydro-[1]benzothiolo[2,3-d]pyrimidine
  参考文献：
  名称：

  Aroylation of Fused Pyrimidines; Synthesis of 4-Aroylfuro[2,3-d]-, 4-Aroylthieno[2,3-d]-, and 4-Aroylisoxazolo[5,4-d]pyrimidines

  摘要：

  4-Aroylfuro[2,3-d]-(4), 4-aroylthieno[2,3-d]-(7 and 8), and 4-aroylisoxazolo[5,4-d]pyrimidines (13) were synthesized by aroylation of the fused chloro-(3a and 12) or bromopyrimidines (3b, 5, and 6) with arenecarbaldehydes (2) catalyzed by an imidazolium salt (1a). The fused aroylpyrimidines (4 and 7) were also synthesized by oxidative decyanation of alpha-phenylheteroareneacetonitriles (10 and 11).

  DOI：

  10.3987/com-97-7914
• 作为产物：
  描述：

  5,6,7,8-四氢-[1]-苯并噻吩[2,3-d]嘧啶-4(1h)-酮 在 ammonium hydroxide 、 三氯氧磷 作用下， 以 1,4-二氧六环 、 水 为溶剂， 反应 4.0h， 生成 5,6,7,8-四氢苯并[4,5]噻吩并[2,3-d]嘧啶-4-胺
  参考文献：
  名称：

  鉴定5,6-取代的4-氨基噻吩并[2,3- d ]嘧啶为LIMK1抑制剂

  摘要：

  4-氨基苯并噻吩并[3,2- d ]嘧啶先前在高通量筛选活动中被鉴定为LIMK1抑制剂。支架逆转导致鉴定了一系列简单的5,6-取代的4-氨基噻吩并[2,3- d ]嘧啶，对LIMK1的抑制作用很小。

  DOI：

  10.1016/j.bmcl.2011.07.050

文献信息

• A One-Step, Atom Economical Synthesis of Thieno[2,3-<i>d</i> ]pyrimidin-4-amine Derivatives by a Four-Component Reaction
  作者：Taoda Shi、ChristopherJ. Zerio、Jared Sivinski、Andrew J. Ambrose、Kohlson T. Moore、Thomas Buckley、Lynn Kaneko、Mae Zhang、Donna D. Zhang、Eli Chapman

  DOI：10.1002/ejoc.201900414

  日期：2019.6.2

  A Na2HPO4-catalyzed four-component reaction between a ketone, malononitrile, S8 and formamide has been realized for the first time. This reaction provides a concise approach to thieno[2,3-d]pyrimidin-4-amines, previously requiring 5 steps. The utility of this reaction was validated by preparing a multi-targeted kinase inhibitor and an inhibitor of the NRF2 pathway with excellent atom- and step-economy

  首次实现了Na2HPO4催化酮、丙二腈、S8和甲酰胺之间的四组分反应。该反应提供了一种制备噻吩并[2,3-d]嘧啶-4-胺的简洁方法，之前需要 5 个步骤。通过制备具有优异原子经济性和步骤经济性的多靶点激酶抑制剂和 NRF2 途径抑制剂，验证了该反应的实用性。
• Synthesis and anticonvulsive activity of a series of new pyrano(thiopyrano,pyrido)-[4′,3′:4,5]thieno[2,3-d]pyrimidines
  作者：A. P. Mkrtchyan、S. G. Kazaryan、A. S. Noravyan、I. A. Dzhagatspanyan、I. M. Nazaryan、A. G. Akopyan

  DOI：10.1007/bf02539219

  日期：1998.9

  and -pyridines ( I IV) [5, 6] and 2-alkyl, 3-, or 4-aminothieno[2,3-d]pyrimidines [4, 5, 7] for the synthesis of new 2-amino-3-ethoxycarbonylthiophene derivatives (V, VI), 2,3-substituted (VIIIX, XIII XVII) and 2,4substituted thieno[2,3-d]pyrimidines (XX, XXI, XXIIIXXIX), and 3,4-(XXXI, XXXII) and 2,3-condensed (XXXIII XL) compounds of the latter pyrimidines. The synthesized compounds were characterized

  之前我们已经建立了噻吩并[2,3-d]嘧啶的化学结构与其药理活性之间的一些关系[1 -4]。在这项工作中，我们使用了缩合 2-amino-3-ethoxyearbonylthieno[2,3-c]pyrans、-thiopyrans 和 -pyridines (I IV) [5, 6] 和 2-烷基、3- 或 4-氨基噻吩并 [2,3-d] 嘧啶 [4, 5, 7] 用于合成新的 2-氨基-3-乙氧基羰基噻吩衍生物 (V, VI)、2,3-取代 (VIIIX, XIII XVII) 和 2,4-取代噻吩并 [2,3-d] 嘧啶 (XX, XXI, XXIIIXXIX)，以及后者嘧啶的 3,4-(XXXI, XXXII) 和 2,3-缩合 (XXXIII XL) 化合物。合成的化合物的特征在于它们的抗惊厥活性。酰化衍生物 V 和 VI 是通过化合物 II 与相应的酸氯酐相互作用获得的。
• Synthesis of 5-Thioxo-hexahydrobenzo[<i>b</i>]thiopheno[2,3-<i>d</i>]-1,2,4-triazolo[1,5-<i>c</i>]pyrimidines and Related Compounds Based on Cyclocondensations of 2-Isothiocyanato-3-cyano-4,5,6,7-tetrahydrobenzo[<i>b</i>]thiophene
  作者：Wolf-Diethard Pfeiffer、Horst Dollinger、Peter Langer

  DOI：10.1080/10426500802243216

  日期：2009.3.10

  5-Thioxo-4,6,8,9,10,11-hexahydro-benzo[b]thiopheno[2,3-d]-1,2,4-triazolo[1,5-c]pyrimidines and related compounds were prepared based on cyclizations of 2-isothiocyanato-3-cyano-4,5,6,7-tetrahydrobenzo[b]thiophene with aminoketones and carboxylic hydrazides.

  5-Thioxo-4,6,8,9,10,11-hexahydro-benzo[b]thiopheno[2,3-d]-1,2,4-triazolo[1,5-c] 嘧啶和相关化合物是基于 2-isothiocyanato-3-cyano-4,5,6,7-四氢苯并[b]噻吩与氨基酮和羧酰肼的环化反应制备。
• Pharmacophore‐based, rationale design, and efficient synthesis of novel tetrahydrobenzo[b]thiophene candidates as potential dual Topo I/II inhibitors and DNA intercalators
  作者：Hager R. Nofal、Ahmed A. Al‐Karmalawy、Ayman Abo Elmaaty、Mahmoud F. Ismail、Ali Khalil Ali、Eslam M. Abbass

  DOI：10.1002/ardp.202400217

  日期：2024.9

  tetrahydrobenzo[b]thiophene derivatives was designed and synthesized as dual topoisomerase (Topo) I/II inhibitors implicating potential DNA intercalation. Ethyl-2-amino-3-cyano-4,5,6,7-tetrahydrobenzo[b]thiophene-4-carboxylate (1) was prepared by modification of the Gewald reaction procedure using a Fe2O3 nanocatalyst and then it was used as a building block for the synthesis of tetrahydrobenzo[b]thiophene candidates

  设计并合成了一系列四氢苯并[ b ]噻吩衍生物作为双拓扑异构酶 (Topo) I/II 抑制剂，涉及潜在的 DNA 嵌入。 2-氨基-3-氰基-4,5,6,7-四氢苯并[ b ]噻吩-4-甲酸乙酯( 1 )是通过使用Fe 2 O 3纳米催化剂改进Gewald反应程序来制备的，然后将其用作合成四氢苯并[ b ]噻吩候选物的结构单元 ( 2-14 )。有趣的是，化合物14对肝细胞、结直肠和乳腺癌细胞系表现出最佳的细胞毒性潜力（IC 50 = 7.79、8.10 和 3.53 µM），分别超过多柔比星对乳腺癌的作用（IC 50 = 4.17 µM）。同时，Topo I 和 II 抑制测定显示，与喜树碱 (IC 50 = 28.34 nM) 和阿霉素 (IC 50 = 28.34 nM) 相比，化合物3在所研究的候选药物中表现出最佳的抑制潜力 (IC 50 = 25.26 和 10.01 nM)。
• Robba,M. et al., Comptes Rendus des Seances de l'Academie des Sciences, Serie C: Sciences Chimiques, 1973, vol. 276, p. 93 - 95
  作者：Robba,M. et al.

  DOI：——

  日期：——