4-phenethyl-5-(thien-2-yl)-4H-3-mercapto-1,2,4-triazole | 525581-59-3

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 4-phenethyl-5-(thien-2-yl)-4H-3-mercapto-1,2,4-triazole
• 英文别名: 4-(2-phenylethyl)-5-(thiophen-2-yl)-4H-1,2,4-triazole-3-thiol；4-(2-phenylethyl)-3-thiophen-2-yl-1H-1,2,4-triazole-5-thione
• CAS: 525581-59-3
• 化学式: C₁₄H₁₃N₃S₂
• mdl: MFCD03801999
• 分子量: 287.409
• InChiKey: LJYFFCVWGYUOHC-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.6
• 重原子数：
  19
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.14
• 拓扑面积：
  88
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  4-phenethyl-5-(thien-2-yl)-4H-3-mercapto-1,2,4-triazole 、 溴甲苯 在 caesium carbonate 作用下， 以 乙腈 为溶剂， 生成 3-Benzylsulfanyl-4-(2-phenylethyl)-5-thiophen-2-yl-1,2,4-triazole
  参考文献：
  名称：

  Triazole derivatives as non-nucleoside inhibitors of HIV-1 reverse transcriptase—Structure–activity relationships and crystallographic analysis

  摘要：

  A series of 3,4,5-trisubstituted 1,2,4-4H triazole derivatives was synthesized and investigated for HIV-1 reverse transcriptase inhibition. An X-ray structure with HIV-1 RT secured the binding mode and allowed the key interactions with the enzyme to be identified.

  DOI：

  10.1016/j.bmcl.2007.11.127
• 作为产物：
  描述：

  N-(2-phenylethyl)-2-(thiophen-2-ylcarbonyl)hydrazinecarbothioamide 在 碳酸氢钠 作用下， 生成 4-phenethyl-5-(thien-2-yl)-4H-3-mercapto-1,2,4-triazole
  参考文献：
  名称：

  Triazole derivatives as non-nucleoside inhibitors of HIV-1 reverse transcriptase—Structure–activity relationships and crystallographic analysis

  摘要：

  A series of 3,4,5-trisubstituted 1,2,4-4H triazole derivatives was synthesized and investigated for HIV-1 reverse transcriptase inhibition. An X-ray structure with HIV-1 RT secured the binding mode and allowed the key interactions with the enzyme to be identified.

  DOI：

  10.1016/j.bmcl.2007.11.127

文献信息

• Asymmetric Synthesis of Enantiomerically Enriched a-Amino Acids Containing 2-Furyl- and 2-Thienyl-1,2,4-triazoles in the Side-Chain
  作者：Ashot S. Saghyan、Hayarpi M. Simonyan、Satenik G. Petrosyan、Anna F. Mkrtchyan、Lilit V. Khachatryan、Arpine V. Geolchanyan、Melanya A. Samvelyan、Tariel V. Ghochikyan、Nazken Kelzhanova、Amanzhan T. Saginayev、Peter Langer

  DOI：10.5560/znb.2014-3221

  日期：2014.4.1

  An efficient method for the asymmetric synthesis of a-amino acids, containing furyl- and thiophenyl-substituted triazoles in their side-chain, is reported. The strategy relies on Michael addition of 3,4,5-substituted 1,2,4-triazoles to the C=C bond of chiral NiII complexes containing the Schiff base formed from dehydroamino acids (dehydroalanine and (E + Z)-dehydroaminobutyric acid) and from chiral auxiliaries, i. e. (S)-2-N-(N0-benzylprolyl)aminobenzophenone and (S)-2-N- (N0-2-chlorobenzylprolyl) aminobenzophenone. The reactions proceeded with good to very good diastereoselectivity. Hydrolysis of the diastereomeric mixtures of metal complexes afforded the enantiomerically pure a-amino acids with high enantiomeric excess (ee> 98%).

  报告了一种高效的方法，用于不对称合成侧链中含有呋喃基和噻吩基取代的三唑的 a-氨基酸。该策略依赖于 3,4,5-取代的 1,2,4-三唑与含有由脱氢氨基酸（脱氢丙氨酸和 (E + Z)- 脱氢氨基丁酸）和手性助剂（即 (S)-2-N- N,N,N-三唑）形成的希夫碱的手性 NiII 复合物的 C=C 键的迈克尔加成。即(S)-2-N-(N0-苄基)氨基二苯甲酮和(S)-2-N-(N0-2-氯苄基)氨基二苯甲酮。这些反应的非对映选择性良好。水解非对映异构体混合物金属络合物可得到对映异构体纯度高（ee> 98%）的 a-氨基酸。
• COMPOUNDS FOR MODULATING RNA BINDING PROTEINS AND USES THEREFOR
  申请人：RYDER Sean

  公开号：US20110065704A1

  公开（公告）日：2011-03-17

  The invention relates to compositions and methods for inhibiting RNA binding proteins (e.g., MEX-3, MEX-5 and POS-1), as well as methods for treating and preventing disorders associated with parasitic infections and inflammatory disorders.
• US8377639B2
  申请人：——

  公开号：US8377639B2

  公开（公告）日：2013-02-19
• US8962244B2
  申请人：——

  公开号：US8962244B2

  公开（公告）日：2015-02-24
• [EN] COMPOUNDS FOR MODULATING RNA BINDING PROTEINS AND USES THEREFOR<br/>[FR] COMPOSÉS DE MODULATION DES PROTÉINES DE LIAISON À L'ARN ET APPLICATIONS ASSOCIÉES
  申请人：UNIV MASSACHUSETTS

  公开号：WO2010151797A2

  公开（公告）日：2010-12-29

  The invention relates to compositions and methods for inhibiting RNA binding proteins (e.g., MEX-3, MEX-5 and POS-1), as well as methods for treating and preventing disorders associated with parasitic infections and inflammatory disorders.