2-amino-1-cyano-4,5-dihydronaphtho<2,1-b>thiophene | 37071-20-8

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: 2-amino-1-cyano-4,5-dihydronaphtho<2,1-b>thiophene
• 英文别名: 2-amino-4,5-dihydro-naphtho[2,1-b]thiophene-1-carbonitrile；2-amino-4,5-dihydronaphtho[2,1-b]thiophene-1-carbonitrile；2-amino-4,5-dihydro-naphtho[2,1-b]thiophene-1-carbonitrile；2-amino-4H,5H-naphtho[2,1-b]thiophene-1-carbonitrile；2-amino-4,5-dihydrobenzo[e][1]benzothiole-1-carbonitrile
• CAS: 37071-20-8
• 化学式: C₁₃H₁₀N₂S
• mdl: MFCD00128275
• 分子量: 226.302
• InChiKey: KMUDCZOBMKTNNP-UHFFFAOYSA-N

物化性质

• 熔点：
  140-142 °C
• 沸点：
  461.3±45.0 °C(Predicted)
• 密度：
  1.35±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.5
• 重原子数：
  16
• 可旋转键数：
  0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.153
• 拓扑面积：
  78
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  2-amino-1-cyano-4,5-dihydronaphtho<2,1-b>thiophene 在 PPA 、 磷酸 、 一水合肼 、 三氯氧磷 作用下， 以 乙醇 为溶剂， 反应 33.0h， 生成 8,9-dihydronaphtho[1',2':4,5]thieno[3,2-e][1,2,4]triazolo[4,3-c]pyrimidine
  参考文献：
  名称：

  具有潜在抗炎活性的噻吩并三唑并嘧啶和噻吩并四唑并嘧啶衍生物的合成和异构化

  摘要：

  从 2-氨基-4,5-二氢萘并 [2,1-b] 噻吩-1-甲腈 (1) 开始制备了几种含有噻吩并 [2,3-d] 嘧啶系统的衍生物。特别是8,9-二氢萘基-[1',2':4,5]噻吩并[3,2-e][1,2,4]三唑并[4,3-c]嘧啶的合成及结构表征衍生物 13-16 及其异构化为 8,9-二氢萘并[1',2':4,5]噻吩并[3,2-e][1,2,4]-三唑并[1,5-c]嘧啶衍生物17-20 在不同的合适反应条件下被报道并用 X 射线分析验证。此外，化合物 13、14 和 22 被测试为潜在的抗炎剂，衍生物 14 在角叉菜胶测试中显示出有效的活性。© 2005 Wiley Periodicals, Inc. 杂原子化学 16:226–234, 2005; 在线发表于 Wiley InterScience (www.interscience.wiley.com)。DOI 10.1002/hc

  DOI：

  10.1002/hc.20114
• 作为产物：
  描述：

  (1,2,3,4-四氢-1-亚萘基)丙二腈 在 sulfur 作用下， 反应 2.5h， 以48%的产率得到2-amino-1-cyano-4,5-dihydronaphtho<2,1-b>thiophene
  参考文献：
  名称：

  Some transformations of 1-(1,2,3,4-tetrahydronaphthylidene)-malononitrile or cyanoacetate

  摘要：

  DOI：

  10.1007/bf00809775

文献信息

• Synthesis and screening of some novel fused thiophene and thienopyrimidine derivatives for anti-avian influenza virus (H5N1) activity
  作者：Aymn E. Rashad、Ahmed H. Shamroukh、Randa E. Abdel-Megeid、Ahmed Mostafa、Rabeh El-Shesheny、Ahmed Kandeil、Mohamed A. Ali、Klaus Banert

  DOI：10.1016/j.ejmech.2010.08.044

  日期：2010.11

  1-b]thiophene-1-carbonitrile (1). Structure characterization of the thioxo derivative 7 was also performed and its reaction with some chloro and bromoalkyl reagents was studied. Moreover, the prepared products were tested for antiviral activity against H5N1 virus [A/chicken/Egypt/1/2006 (H5N1)] by determination of both EC50 and LD50 and confirmed by plaque reduction assay on MDCK cells. Compounds 5, 7 and 8 showed

  从2-氨基-4,5-二氢萘并[2,1- b ]噻吩-1开始，制备了几种含有二氢萘，萘[ 2,1- b ]噻吩和噻吩并[2,3- d ]嘧啶环系统的衍生物。腈（1）。还进行了thioxo衍生物7的结构表征，并研究了其与某些氯和溴代烷基试剂的反应。此外，通过确定EC 50和LD 50来测试制备的产物对H5N1病毒的抗病毒活性[A /鸡/埃及/ 1/2006（H5N1）]，并通过在MDCK细胞上的噬斑减少试验来证实。化合物5，7和8 与其他测试化合物相比，显示出最高的效果。
• A Convenient Synthesis of New 2-Cyanomethylthieno[3,2-e][1,2,4]- triazolo[1,5-c]pyrimidine Derivatives
  作者：Dhiab Jabli、Khaireddine Dridi、Mohamed L. El Efrit

  DOI：10.2174/1570178611666140311005612

  日期：2014.4

  A new series of 2-cyanomethylthienotriazolopyrimidines has been synthesized in good yield through a facile method using substituted aminothiophene-3-carbonitrile as building block and cyanoacetic acid hydrazide as reagent in one framework. The structure of the synthesized compounds was established on the basis of their mass and spectral data.

  以取代氨基噻吩-3-腈为结构单元，氰基乙酸酰肼为试剂的简便方法，通过简便的方法合成了一系列新的2-氰基甲基噻吩并三氮杂并嘧啶并以高收率合成。根据合成化合物的质量和光谱数据确定其结构。
• Thienopyrimidine Ureas as Novel and Potent Multitargeted Receptor Tyrosine Kinase Inhibitors
  作者：Yujia Dai、Yan Guo、Robin R. Frey、Zhiqin Ji、Michael L. Curtin、Asma A. Ahmed、Daniel H. Albert、Lee Arnold、Shannon S. Arries、Teresa Barlozzari、Joy L. Bauch、Jennifer J. Bouska、Peter F. Bousquet、George A. Cunha、Keith B. Glaser、Jun Guo、Junling Li、Patrick A. Marcotte、Kennan C. Marsh、Maria D. Moskey、Lori J. Pease、Kent D. Stewart、Vincent S. Stoll、Paul Tapang、Neil Wishart、Steven K. Davidsen、Michael R. Michaelides

  DOI：10.1021/jm050458h

  日期：2005.9.1

  A series of novel thienopyrimidine-based receptor tyrosine kinase inhibitors has been discovered. Investigation of structure-activity relationships at the 5- and 6-positions of the thienopyrimidine nucleus led to a series of N,N '-diaryl ureas that potently inhibit all of the vascular endothelial growth factor (VEGF) and platelet-derived growth factor (PDGF) receptor tyrosine kinases. A kinase insert domain-containing receptor (KDR) homology model suggests that these compounds bind to the "inactive conformation" of the enzyme with the urea portion extending into the back hydrophobic pocket adjacent to the adenosine 5 '-triphosphate (ATP) binding site. A number of compounds have been identified as displaying excellent in vivo potency. In particular, compounds 28 and 76 possess favorable pharmacokinetic (PK) profiles and demonstrate potent antitumor efficacy against the HT1080 human fibrosarcoma xenograft tumor growth model (tumor growth inhibition (TGI) = 75% at 25 mg/kg-day, per os (po)).
• 2,4-Diaminothieno[2,3-d]pyrimidines as antifolates and antimalarials. 3. Synthesis of 5,6-disubstituted derivatives and related tetracyclic analogs
  作者：A. Rosowsky、K. K. N. Chen、M. Lin

  DOI：10.1021/jm00261a004

  日期：1973.3
• Taylor,E.C.; Berger,J.G., Angewandte Chemie, 1966, vol. 78, p. 144
  作者：Taylor,E.C.、Berger,J.G.

  DOI：——

  日期：——