octyl carbazate | 90796-71-7

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: octyl carbazate
• 英文别名: Carbazinsaeureoctylester；Hydrazin-carbonsaeure-octylester；octyl N-aminocarbamate
• CAS: 90796-71-7
• 化学式: C₉H₂₀N₂O₂
• 分子量: 188.27
• InChiKey: GUNYCYYPDJWVSY-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  13
• 可旋转键数：
  8
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.89
• 拓扑面积：
  64.4
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  octyl carbazate 、 (E)-3-(5-硝基-2-呋喃基)丙烯醛 在 对甲苯磺酸 作用下， 以 甲苯 为溶剂， 以15%的产率得到octyl N-[(E)-[(E)-3-(5-nitrofuran-2-yl)prop-2-enylidene]amino]carbamate
  参考文献：
  名称：

  New potent 5-nitrofuryl derivatives as inhibitors of Trypanosoma cruzi growth. 3D-QSAR (CoMFA) studies

  摘要：

  Growth inhibitory activity in vitro of sixteen new 5-nitrofuryl derivatives against the protozoan parasite Trypanosoma cruzi, the causative agent of American trypanosomiasis, was studied. The designed compounds combine in the same molecule the recognized 5-nitrofuryl group, an oxidative stress promoter, and lateral chains that could interact with biomolecules such as trypanothione reductase. Some of the derivatives were found to be very active against the epimastigote form of the parasite, being near to 3.0-fold more active than the reference compound, nifurtimox. Moreover, three-dimensional requirements for activity were clearly observed using a 3D-QSAR study based on a comparative molecular field analysis (CoMFA). The best CoMFA model, r(2) = 0.970 and q(2) = 0.725, points to the importance of a specific hydrogen-bonding pattern around the carbonyl or thiocarbonyl moieties, as well as the requirement for hydrophobic lateral chains. Theoretical pharmacokinetics (Lipinski's rule, PSA) supports further in vivo studies. (c) 2006 Elsevier SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2005.11.008

文献信息

• Design, synthesis and biological evaluation of new potent 5-nitrofuryl derivatives as anti-Trypanosoma cruzi agents. Studies of trypanothione binding site of trypanothione reductase as target for rational design
  作者：Gabriela Aguirre、Eliana Cabrera、Hugo Cerecetto、Rossanna Di Maio、Mercedes González、Gustavo Seoane、Adelina Duffaut、Ana Denicola、María J. Gil、Victor Martínez-Merino

  DOI：10.1016/j.ejmech.2004.02.007

  日期：2004.5

  Design, using force-field calculations on the catalytic site of trypanothione reductase from Trypanosoma cruzi, has led to the development of new 5-nitrofuryl derivatives as potential anti-trypanosomal agents. The synthesized compounds were tested in vitro against T cruzi and more than 75% of the prepared derivatives showed higher activity than nifurtimox. Compounds 5 and 11, hexyl 4-(5-nitrofurfurylidene)carbazate and N-hexyl 3-(5-nitrofuryl)propenamide, showed the highest in vitro trypanocidal effect reported to date for members of the nitrofuran family. Partition coefficients and energies for the single-electron reduction of compounds were theoretically determined. These properties could be not the major cause of the activities' differences. The physicochemical environment around E 19, W22, C53 and Y111 residues within the trypanothione binding site of trypanothione reductase resulted a valuable target for the rational design of anti-trypanosomal drugs. (C) 2004 Elsevier SAS. All rights reserved.