1-Phenyl-3-[2-(4-sulfamoylphenyl)ethyl]thiourea | 10079-93-3

• 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: 1-Phenyl-3-[2-(4-sulfamoylphenyl)ethyl]thiourea
• CAS: 10079-93-3
• 化学式: C₁₅H₁₇N₃O₂S₂
• mdl: MFCD01975340
• 分子量: 335.451
• InChiKey: QOWRADOKRZQCAQ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2
• 重原子数：
  22
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.13
• 拓扑面积：
  125
• 氢给体数：
  3
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  1-Phenyl-3-[2-(4-sulfamoylphenyl)ethyl]thiourea 在 哌啶 、 sodium acetate 作用下， 以 甲醇 、 乙醇 为溶剂， 反应 36.0h， 生成 4-(2-((E)-5-((Z)-4-formylbenzylidene)-4-oxo-2-(phenylimino)thiazolidin-3-yl)ethyl)benzenesulfonamide
  参考文献：
  名称：

  磺酰胺-噻唑烷-4-酮杂化物的设计、合成、分子动力学模拟、DFT分析、计算药理学和解码抗糖尿病分子机制

  摘要：

  为了寻找新型抗糖尿病药物，该研究旨在杂交和合成基于苯磺酰胺和噻唑烷-4-酮支架的分子，高效合成（6小时），并通过 FTIR、H NMR、C NMR 和 HRMS 光谱进行结构表征。基于α-淀粉酶抑制、葡萄糖摄取测定和PPAR-γ转录因子测定评估抗糖尿病活性。化合物（4-（2-（（E）-5-（（Z）-2-羟基亚苄基）-4-氧代-2-（苯基亚氨基）噻唑烷-3-基）乙基）苯磺酰胺）对α-淀粉酶表现出良好的活性抑制作用的IC值为μg/ml。对化合物进行葡萄糖摄取测定6小时以评估葡萄糖摄取的能力。其中，Compound 在酵母细胞系中表现出显着的葡萄糖摄取率，达 88.71%。为了支持化合物的葡萄糖摄取结果，与吡格列酮相比，测量了化合物的PPAR-γ转录因子的表达。此外，进行诱导拟合对接以预测 α-淀粉酶结合口袋中合成化合物的精细姿势。 MD模拟研究证实了α-淀粉酶结合袋中化合物的稳定性。使用 B3LYP

  DOI：

  10.1016/j.molstruc.2024.138359
• 作为产物：
  描述：

  硫代异氰酸苯酯 、 4-(2-氨乙基)苯磺酰胺 在 三乙胺 作用下， 以 四氢呋喃 为溶剂， 生成 1-Phenyl-3-[2-(4-sulfamoylphenyl)ethyl]thiourea
  参考文献：
  名称：

  Carbonic anhydrase inhibitors - Part 49: Synthesis of substituted ureido and thioureido derivatives of aromatic/heterocyclic sulfonamides with increased affinities for isozyme I

  摘要：

  Reaction of nine aromatic/heterocyclic sulfonamides containing a free amino group with aryl isocyanates/isothiocyanates or allyl isothiocyanate afforded the corresponding urea/thiourea derivatives, which were characterized by standard physico-chemical procedures and assayed as inhibitors of three isozymes of carbonic anhydrase (CA), i.e. hCA I, hCA II and bCA IV (h = human, b = bovine isozyme). Another series of compounds, 1,5-disubstituted-2-thiobiuret derivatives, were prepared by reaction of 3,4-dichlorophenyl isocyanate with thioureido-containing aromatic/heterocyclic sulfonamides. Good inhibition of all these three CA isozymes was observed with the new compounds, but an exciting finding was that the ureas/thioureas and especially the above-mentioned thiobiurets reported here have an increased affinity to the slow isozyme hCA I, generally less susceptible to inhibition by sulfonamides, as compared to the rapid isozymes hCA II and bCA IV. Some of the new compounds might constitute good lead molecules for developing more selective CA I inhibitors. (C) Elsevier, Paris.

  DOI：

  10.1016/s0223-5234(98)80033-0

文献信息

• INHIBITORS OF CARBONIC ANHYDRASE IX
  申请人：Zimmerman Craig

  公开号：US20090175794A1

  公开（公告）日：2009-07-09

  Novel radiopharmaceuticals that are useful in diagnostic imaging and therapeutic treatment of disease characterized by over expression of CA-IX comprise a complex that contains a sulfonamide moiety which is capable of binding the active catalytic site of CA-IX, and a radionuclide adapted for radioimaging and/or radiotherapy:

  具有在诊断成像和治疗过度表达CA-IX疾病中有用的新型放射性药物，包括一种含有磺胺基团的复合物，该基团能够结合CA-IX的活性催化位点，以及适用于放射成像和/或放射治疗的放射性核素：
• Carbonic anhydrase inhibitors - Part 49: Synthesis of substituted ureido and thioureido derivatives of aromatic/heterocyclic sulfonamides with increased affinities for isozyme I
  作者：Claudiu T. Supuran、Andrea Scozzafava、Bogdan C. Jurca、Marc A. Ilies

  DOI：10.1016/s0223-5234(98)80033-0

  日期：1998.2

  Reaction of nine aromatic/heterocyclic sulfonamides containing a free amino group with aryl isocyanates/isothiocyanates or allyl isothiocyanate afforded the corresponding urea/thiourea derivatives, which were characterized by standard physico-chemical procedures and assayed as inhibitors of three isozymes of carbonic anhydrase (CA), i.e. hCA I, hCA II and bCA IV (h = human, b = bovine isozyme). Another series of compounds, 1,5-disubstituted-2-thiobiuret derivatives, were prepared by reaction of 3,4-dichlorophenyl isocyanate with thioureido-containing aromatic/heterocyclic sulfonamides. Good inhibition of all these three CA isozymes was observed with the new compounds, but an exciting finding was that the ureas/thioureas and especially the above-mentioned thiobiurets reported here have an increased affinity to the slow isozyme hCA I, generally less susceptible to inhibition by sulfonamides, as compared to the rapid isozymes hCA II and bCA IV. Some of the new compounds might constitute good lead molecules for developing more selective CA I inhibitors. (C) Elsevier, Paris.
• Design, synthesis, molecular dynamic simulation, DFT analysis, computational pharmacology and decoding the antidiabetic molecular mechanism of sulphonamide-thiazolidin-4-one hybrids
  作者：Shriram D. Ranade、Shankar G. Alegaon、Nayeem A. Khatib、Shankar Gharge、Rohini S. Kavalapure、B.R. Prashantha Kumar

  DOI：10.1016/j.molstruc.2024.138359

  日期：2024.9

  the refined pose of synthesized compounds in the α-amylase binding pocket. MD simulation studies confirmed the stability of compound in the α-amylase binding pocket. Molecules were geometrically optimized by DFT theory using B3LYP 6–31 G (d, p**) basis set, and electronic properties were studied. Network pharmacology analysis for compound identified key pathways involved in T2DM and postprandial hyperglycemia

  为了寻找新型抗糖尿病药物，该研究旨在杂交和合成基于苯磺酰胺和噻唑烷-4-酮支架的分子，高效合成（6小时），并通过 FTIR、H NMR、C NMR 和 HRMS 光谱进行结构表征。基于α-淀粉酶抑制、葡萄糖摄取测定和PPAR-γ转录因子测定评估抗糖尿病活性。化合物（4-（2-（（E）-5-（（Z）-2-羟基亚苄基）-4-氧代-2-（苯基亚氨基）噻唑烷-3-基）乙基）苯磺酰胺）对α-淀粉酶表现出良好的活性抑制作用的IC值为μg/ml。对化合物进行葡萄糖摄取测定6小时以评估葡萄糖摄取的能力。其中，Compound 在酵母细胞系中表现出显着的葡萄糖摄取率，达 88.71%。为了支持化合物的葡萄糖摄取结果，与吡格列酮相比，测量了化合物的PPAR-γ转录因子的表达。此外，进行诱导拟合对接以预测 α-淀粉酶结合口袋中合成化合物的精细姿势。 MD模拟研究证实了α-淀粉酶结合袋中化合物的稳定性。使用 B3LYP