3-Cyano-5,8-ethano-5,6,7,8-tetrahydro-1,5-naphthyridine-2(1H)-thione | 125366-05-4

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二氮杂萘
• 英文名称: 3-Cyano-5,8-ethano-5,6,7,8-tetrahydro-1,5-naphthyridine-2(1H)-thione
• 英文别名: 6-thioxo-3,4,5,6-tetrahydro-2H-1,4-ethano-1,5-naphthyridine-7-carbonitrile；5-sulfanylidene-1,6-diazatricyclo[6.2.2.02,7]dodeca-2(7),3-diene-4-carbonitrile
• CAS: 125366-05-4
• 化学式: C₁₁H₁₁N₃S
• 分子量: 217.294
• InChiKey: QAXCWVKHXLELBY-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.9
• 重原子数：
  15
• 可旋转键数：
  0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.45
• 拓扑面积：
  71.2
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  3-Cyano-5,8-ethano-5,6,7,8-tetrahydro-1,5-naphthyridine-2(1H)-thione 在 氢氧化钾 、 碘 作用下， 以 氯仿 、 N,N-二甲基甲酰胺 为溶剂， 反应 12.0h， 生成
  参考文献：
  名称：

  Stereochemistry of electrophilic annelation of 2-allyl- (and 2-cyclohexen-1-yl)thio-1,5-naphthyridines to thiazolo]3,2-a]-1,5-naphthyridinium salts

  摘要：

  DOI：

  10.1007/bf00480768
• 作为产物：
  描述：

  2-氰基硫代乙酰胺 、 sodium;(3-oxo-1-azabicyclo[2.2.2]octan-2-ylidene)methanolate 在 溶剂黄146 作用下， 以 乙醇 为溶剂， 反应 0.5h， 以65%的产率得到3-Cyano-5,8-ethano-5,6,7,8-tetrahydro-1,5-naphthyridine-2(1H)-thione
  参考文献：
  名称：

  Stereochemistry of electrophilic annelation of 2-allyl- (and 2-cyclohexen-1-yl)thio-1,5-naphthyridines to thiazolo]3,2-a]-1,5-naphthyridinium salts

  摘要：

  DOI：

  10.1007/bf00480768

文献信息

• N-Cyanochloroacetamidine — A convenient reagent for the regioselective synthesis of fused diaminopyrimidines
  作者：Vasilii A Artyomov、Lyudmila A Rodinovskaya、Anatolii M Shestopalov、Viktor P Litvinov

  DOI：10.1016/0040-4020(95)00935-3

  日期：1996.1

  enaminocyanamidines form pyrimidine rings under acid or base catalysis forming fused diaminopyrimidines. According to this common scheme, functionally substituted thieno[3,2-d]pyrimidines, thiazolo[4,5-d]pyrimidines, pyrimido[4″,5″:4′,5′]thieno[3′,2′:4,5]thieno[3,2-d]pyrimidine, pyrido[3′,2′4,5]thieno(selenopheno)[3,2-d]pyrimidines, their hydrogenated analogues, and pyrimido-[4′,5′:4,5]thieno[2,3-d]pyrimidine were synthesized

  N-氰基氯乙酰胺与共轭的巯基（硒代）腈反应，生成区域选择性S（Se）烷基化产物，该产物随后可参与Thorpe反应。所得的烯氨基氰在酸或碱催化下形成嘧啶环，形成稠合的二氨基嘧啶。根据该通用方案，功能性取代的噻吩并[3,2- d ]嘧啶，噻唑并[4,5- d ]嘧啶，嘧啶并[4“，5”：4'，5']噻吩并[3'，2'： 4,5] thieno [3,2- d ]嘧啶，吡啶基[3'，2'4,5] thieno（硒代苯酚）[3,2- d ]嘧啶，它们的氢化类似物和嘧啶-[4'，5 ′：4，5]噻吩并[2，3- d ]嘧啶。
• Regioselective synthesis of substituted thieno[2,3-b]pyrimidines and pyrido[3?,2?:4,5]thienopyrimidines and their [3,2-d]selenopheno analogs from 3-cyanopyridine-2(1H)-thiones, 3-cyano-pyridine-2(1H)-selenones, and N-cyanochloracetamidine
  作者：V. A. Artemov、L. A. Rodinovskaya、A. M. Shestopalov、V. P. Litvinov

  DOI：10.1007/bf01164746

  日期：1994.1
• 3-Amino-thieno[2,3-b]pyridines as microtubule-destabilising agents: Molecular modelling and biological evaluation in the sea urchin embryo and human cancer cells
  作者：Chatchakorn Eurtivong、Victor Semenov、Marina Semenova、Leonid Konyushkin、Olga Atamanenko、Jóhannes Reynisson、Alex Kiselyov

  DOI：10.1016/j.bmc.2016.11.041

  日期：2017.1

  A series of 3-amino-thieno[2,3-b]pyridines was prepared and tested in a phenotypic sea urchin embryo assay to identify potent and specific molecules that affect tubulin dynamics. The most active compounds featured a tricyclic core ring system with a fused cycloheptyl or cyclohexyl substituent and unsubstituted or alkyl-substituted phenyl moiety tethered via a carboxamide. Low nano-molar potency was observed in the sea urchin embryos for the most active compounds (1-5) suggestive of a microtubule-destabilising effect. The molecular modelling studies indicated that the tubulin colchicine site is inhibited, which often leads to microtubule-destabilisation in line with the sea urchin embryo results. Finally, the identified hits displayed a robust growth inhibition (GI(50) of 50-250 nM) of multidrug-resistant melanoma MDA-MB-435 and breast MDA-MB-468 human cancer cell lines. This work demonstrates that for the thieno[2,3-b]pyridines the most effective mechanism of action is microtubule-destabilisation initiated by binding to the colchicine pocket. (C) 2016 Elsevier Ltd. All rights reserved.
• SHESTOPALOV, A. M.;NESTEROV, V. N.;SHARANIN, YU. A.;LITVINOV, V. P.;MORTI+, XIMIYA GETEROTSIKL. SOED.,(1989) N, S. 557-563
  作者：SHESTOPALOV, A. M.、NESTEROV, V. N.、SHARANIN, YU. A.、LITVINOV, V. P.、MORTI+

  DOI：——

  日期：——
• Stereochemistry of electrophilic annelation of 2-allyl- (and 2-cyclohexen-1-yl)thio-1,5-naphthyridines to thiazolo]3,2-a]-1,5-naphthyridinium salts
  作者：A. M. Shestopalov、V. N. Nesterov、Yu. A. Sharanin、V. P. Litvinov、V. Yu. Mortikov、V. E. Shklover、Yu. T. Struchkov

  DOI：10.1007/bf00480768

  日期：1989.4