(4-oxo-3-phenyl-3,4,5,6,7,8-hexahydro-benzo[4,5]thieno[2,3-d]pyrimidin-2-ylsulfanyl)-acetic acid ethyl ester | 59898-81-6

• 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-oxo-3-phenyl-3,4,5,6,7,8-hexahydro-benzo[4,5]thieno[2,3-d]pyrimidin-2-ylsulfanyl)-acetic acid ethyl ester
• 英文别名: Ethyl [(4-oxo-3-phenyl-3,4,5,6,7,8-hexahydro[1]benzothieno[2,3-d]pyrimidin-2-yl)sulfanyl]acetate；ethyl 2-[(4-oxo-3-phenyl-5,6,7,8-tetrahydro-[1]benzothiolo[2,3-d]pyrimidin-2-yl)sulfanyl]acetate
• CAS: 59898-81-6
• 化学式: C₂₀H₂₀N₂O₃S₂
• mdl: MFCD00128321
• 分子量: 400.522
• InChiKey: YBUVCMGKGINWPF-UHFFFAOYSA-N

物化性质

• 沸点：
  591.5±60.0 °C(Predicted)
• 密度：
  1.40±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.9
• 重原子数：
  27
• 可旋转键数：
  6
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.35
• 拓扑面积：
  113
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  环己酮 在 吗啉 、 sodium methylate 、 sulfur 作用下， 以 乙醇 为溶剂， 生成 (4-oxo-3-phenyl-3,4,5,6,7,8-hexahydro-benzo[4,5]thieno[2,3-d]pyrimidin-2-ylsulfanyl)-acetic acid ethyl ester
  参考文献：
  名称：

  Design, synthesis, molecular docking and biological evaluation of thiophen-2-iminothiazolidine derivatives for use against Trypanosoma cruzi

  摘要：

  In this study, we designed and synthesized a series of thiophen-2-iminothiazolidine derivatives from thiophen-2-thioureic with good anti-Trypanosoma cruzi activity. Several of the final compounds displayed remarkable trypanocidal activity. The ability of the new compounds to inhibit the activity of the enzyme cruzain, the major cysteine protease of T. cruzi, was also explored. The compounds 3b, 4b, 8b and 8c were the most active derivatives against amastigote form, with significant IC50 values between 9.7 and 6.03 mu M. The 8c derivative showed the highest potency against cruzain 9IC(50) = 2.4 mu M). Molecular docking study showed that this compound can interact with subsites S1 and S2 simultaneously, and the negative values for the theoretical energy binding (E-b = -7.39 kcal.mol(-1)) indicates interaction 9via dipol-dipole) between the hybridized sulfur sp(3) atom at the thiazolidine ring and Gly66. Finally, the results suggest that the thiophen-2-iminothiazolidines synthesized are important lead compounds for the continuing battle against Chagas disease. (C) 2016 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2016.07.013

文献信息

• Synthesis of 3‐substituted thieno[2,3‐d]pyrimidin‐4 (3H)‐one‐2‐mercaptoacetic acids and their ethyl esters for pharmacological screening
  作者：M.B. Devani、C.J. Shishoo、U.S. Pathak、S.H. Parikh、G.F. Shah、A.C. Padhya

  DOI：10.1002/jps.2600650507

  日期：1976.5

  3-Substituted thieno [2, 3-d] pyrimidin-4(3H)-one-2-mercaptoacetic acids and their ethyl esters were synthesized from 2-mercaptothieno [2, 3-d] pyrimidin-4(3H]-ones, which were obtained by cyclization of thienylthioureas in acidic medium. Analgesic, anti-inflammatory, and anticonvulsant activities were found in some of these compounds. Significant antimicrobial activity was exhibited by thienylthioureas

  由2-巯基噻吩并[2,3-d]嘧啶-4（3H）-合成3-取代的噻吩并[2,3-d]嘧啶-4（3H）-one-2-巯基乙酸及其乙酯。噻吩硫脲在酸性介质中环化获得的化合物具有镇痛，抗炎和抗惊厥活性，噻吩硫脲具有显着的抗菌活性。
• DEVANI M. B.; SHISHOO C. J.; PATHAK U. S.; PARIKH S. H.; SHAH G. F.; PADH+, J. PHARM. SCI., 1976, 65, NO 5, 660-664
  作者：DEVANI M. B.、 SHISHOO C. J.、 PATHAK U. S.、 PARIKH S. H.、 SHAH G. F.、 PADH+

  DOI：——

  日期：——
• Design, synthesis, molecular docking and biological evaluation of thiophen-2-iminothiazolidine derivatives for use against Trypanosoma cruzi
  作者：E.F. Silva-Júnior、E.P.S. Silva、P.H.B. França、J.P.N. Silva、E.O. Barreto、E.B. Silva、R.S. Ferreira、C.C. Gatto、D.R.M. Moreira、J.L. Siqueira-Neto、F.J.B. Mendonça-Júnior、M.C.A. Lima、J.H. Bortoluzzi、M.T. Scotti、L. Scotti、M.R. Meneghetti、T.M. Aquino、J.X. Araújo-Júnior

  DOI：10.1016/j.bmc.2016.07.013

  日期：2016.9

  In this study, we designed and synthesized a series of thiophen-2-iminothiazolidine derivatives from thiophen-2-thioureic with good anti-Trypanosoma cruzi activity. Several of the final compounds displayed remarkable trypanocidal activity. The ability of the new compounds to inhibit the activity of the enzyme cruzain, the major cysteine protease of T. cruzi, was also explored. The compounds 3b, 4b, 8b and 8c were the most active derivatives against amastigote form, with significant IC50 values between 9.7 and 6.03 mu M. The 8c derivative showed the highest potency against cruzain 9IC(50) = 2.4 mu M). Molecular docking study showed that this compound can interact with subsites S1 and S2 simultaneously, and the negative values for the theoretical energy binding (E-b = -7.39 kcal.mol(-1)) indicates interaction 9via dipol-dipole) between the hybridized sulfur sp(3) atom at the thiazolidine ring and Gly66. Finally, the results suggest that the thiophen-2-iminothiazolidines synthesized are important lead compounds for the continuing battle against Chagas disease. (C) 2016 Elsevier Ltd. All rights reserved.