4-amino-6,7,8,9-tetrahydro-5H-cyclohepta[4,5]thieno[2,3-d]pyrimidine

• 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
• 英文名称: 4-amino-6,7,8,9-tetrahydro-5H-cyclohepta[4,5]thieno[2,3-d]pyrimidine
• 英文别名: 6,7,8,9-tetrahydro-5H-cyclohepta[4,5]thieno[2,3-d]pyrimidin-4-amine；1,2-dihydro-1-aminocyclohepta(b)thieno[2,3-d]pyrimidine；8-thia-4,6-diazatricyclo[7.5.0.02,7]tetradeca-1(9),2,4,6-tetraen-3-amine
• 化学式: C₁₁H₁₃N₃S
• mdl: MFCD00126447
• 分子量: 219.31
• InChiKey: WKVBWBRXKVWYEO-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3
• 重原子数：
  15
• 可旋转键数：
  0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.454
• 拓扑面积：
  80
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  2-氨基-5,6,7,8-四氢-4H-环庚基[b]噻吩-3-甲腈 在 ammonium hydroxide 、 sodium ethanolate 、 乙酸酐 作用下， 以 甲醇 、 乙醇 为溶剂， 反应 21.0h， 生成 4-amino-6,7,8,9-tetrahydro-5H-cyclohepta[4,5]thieno[2,3-d]pyrimidine
  参考文献：
  名称：

  Studies with Polyfunctionality Substituted Heterocycles: Novel Syntheses of Thienopyrimido-1,2,4-triazoles

  摘要：

  Several 3-substituted-(un)-cyclohepta(b)thieno[2,3-d]pyrimido[3,4-a]-1,2,4-triazoles 10, 11, 12, 13, and 14 were prepared by reaction of an appropriate substituted 2-amino-3-cyanothiophene 1 with aliphatic acids or benzoyl chloride. Also the fusion of 1 with urea, thiourea to give the corresponding 2-oxo or thioxo-4-aminopyrimidine derivatives 6a, b and other reactions of compound 1 are reported.

  DOI：

  10.1080/10426500210219

文献信息

• Identification of 5,6-substituted 4-aminothieno[2,3-d]pyrimidines as LIMK1 inhibitors
  作者：Brad E. Sleebs、George Nikolakopoulos、Ian P. Street、Hendrik Falk、Jonathan B. Baell

  DOI：10.1016/j.bmcl.2011.07.050

  日期：2011.10

  4-Aminobenzothieno[3,2-d]pyrimidines were previously identified in a high throughput screening campaign as LIMK1 inhibitors. Scaffold reversal led to the identification of a series of simple 5,6-substituted 4-aminothieno[2,3-d]pyrimidines with low micromolar inhibition of LIMK1.

  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。
• Synthesis, Characterization and Biological Studies of Some Novel Thieno[2,3-d]pyrimidines
  作者：Khulud M. Al-Taisan、Hassan M. A. Al-Hazimi、Shar S. Al-Shihry

  DOI：10.3390/molecules15063932

  日期：——

  Several 2-unsubstituted thieno[2,3-d]pyrimidines have been prepared from 2-aminothiophene-3-carboxylic acid esters and their carbonitrile analogs. Some triazolo-thienopyrimidine and 2-thioxothienopyrimidine representatives have also been synthesized using thermal and microwave (MW) irradiation techniques. Structures of the prepared compounds were elucidated on the basis of IR, NMR, 2D NMR and mass

  已经从 2-氨基噻吩-3-羧酸酯及其腈类似物制备了几种 2-未取代的噻吩并 [2,3-d] 嘧啶。一些三唑并噻吩并嘧啶和 2-硫代噻吩并嘧啶的代表也已使用热和微波 (MW) 辐射技术合成。基于红外、核磁共振、二维核磁共振和质谱数据阐明了所制备化合物的结构。还检查了一些选定的合成化合物的生物活性。
• Efficient Constructions of the Four Different Thienopyrimidinone Skeletons via Various Cyclocondensation of o-Aminothienonitrile with Carbonyl Compounds
  作者：Jiarong Li、Junjuan Yang、Daxin Shi、Kai Zhang、Zhangtao Zhao、Fadong Qiu、Yujiao Bi

  DOI：10.3987/com-16-13427

  日期：——

  A series of new thienopyrimidinone derivatives were synthesized via a novel, straightforward and efficient tandem cyclo condensation of o-aminothienonitrile 1 and carbonyl compounds 2 in different conditions. The synthesized four thienopyrimidinone skeletons were thieno[2,3-d]pyrimidinone 3, tert-hydroxythieno[2,3-d]pyrimidinone 4, symmetrical tetracycle thienothiophene-pyrimidone 5 and thienopyrimidine 6 respectively. Their plausible mechanisms were proposed. The properties of compound 5 were investigated.