1-[2-(Cyclohexen-1-yl)ethyl]-3-(4-propan-2-ylphenyl)thiourea | 885398-08-3

• 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-[2-(Cyclohexen-1-yl)ethyl]-3-(4-propan-2-ylphenyl)thiourea
• CAS: 885398-08-3
• 化学式: C₁₈H₂₆N₂S
• 分子量: 302.484
• InChiKey: HAOPMUDWCQUVFA-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.7
• 重原子数：
  21
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  56.2
• 氢给体数：
  2
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  1-[2-(Cyclohexen-1-yl)ethyl]-3-(4-propan-2-ylphenyl)thiourea 在 氢溴酸 作用下， 以75%的产率得到4-isopropylphenyl(1-selena-3-azaspiro[5.5]undec-2-en-2-yl)amine hydrobromide
  参考文献：
  名称：

  Solubility and Solution Thermodynamics of Novel Bicyclic Derivatives of 1,3-Selenazine in Biological Relevant Solvents

  摘要：

  Drug-like N-substituted 1-selena-3-azaspiro[5,5]undec-2-en-2-amine hydrobromides (1:1) have been synthesized. Phenyl, isopropylphenyl, and fluorophenyl substituents were used. The solubility of the obtained compounds in pharmaceutically relevant solvents within the temperature range from (298.15 to 318.15) K has been measured using the isothermal saturation technique. All of the compounds studied appear to have poor solubility of similar to 10(-6) mole fraction in phosphate buffer pH 7.4 and hexane. The solubility values enlarge substantially to similar to 10(-2) and 10(-4) mole fraction, respectively, in octanol and muriatic buffer solution pH 2.0. The solubility of the selenazines in aqueous media was shown to increase as the number of protonated forms grew. The high solubility of the compounds in octanol was found to depend on the formation of intermolecular solvent solute hydrogen bonds. Thermodynamic solubility functions for the substances in the solvents studied have been calculated. The solubility in all of the systems with the predominant enthalpy term of Gibbs energy was proved to increase as the dissolution enthalpy decreased.

  DOI：

  10.1021/je500363r
• 作为产物：
  描述：

  、 2-(1-环己烯基)乙胺 以 丙酮 为溶剂， 生成 1-[2-(Cyclohexen-1-yl)ethyl]-3-(4-propan-2-ylphenyl)thiourea
  参考文献：
  名称：

  Solubility and Solution Thermodynamics of Novel Bicyclic Derivatives of 1,3-Selenazine in Biological Relevant Solvents

  摘要：

  Drug-like N-substituted 1-selena-3-azaspiro[5,5]undec-2-en-2-amine hydrobromides (1:1) have been synthesized. Phenyl, isopropylphenyl, and fluorophenyl substituents were used. The solubility of the obtained compounds in pharmaceutically relevant solvents within the temperature range from (298.15 to 318.15) K has been measured using the isothermal saturation technique. All of the compounds studied appear to have poor solubility of similar to 10(-6) mole fraction in phosphate buffer pH 7.4 and hexane. The solubility values enlarge substantially to similar to 10(-2) and 10(-4) mole fraction, respectively, in octanol and muriatic buffer solution pH 2.0. The solubility of the selenazines in aqueous media was shown to increase as the number of protonated forms grew. The high solubility of the compounds in octanol was found to depend on the formation of intermolecular solvent solute hydrogen bonds. Thermodynamic solubility functions for the substances in the solvents studied have been calculated. The solubility in all of the systems with the predominant enthalpy term of Gibbs energy was proved to increase as the dissolution enthalpy decreased.

  DOI：

  10.1021/je500363r

文献信息

• Synthesis, biological activity, distribution and membrane permeability of novel spiro-thiazines as potent neuroprotectors
  作者：Svetlana V. Blokhina、Tatyana V. Volkova、Marina V. Ol'khovich、Angelica V. Sharapova、Alexey N. Proshin、Sergey O. Bachurin、German L. Perlovich

  DOI：10.1016/j.ejmech.2014.02.052

  日期：2014.4

  New spiro-derivatives of 1,3-thiazine-potential neuroprotectors have been synthesized. It has been determined that the obtained compounds are biologically active and capable of blocking the glutamate-induced calcium ion uptake into synaptosomes of rat brain cortex. The inhibitory activity of the test substances was shown to depend on the chemical nature and structure of the substituents bound with an exocyclic nitrogen atom. Non-polar alkyl and polar radicals with halogen, oxygen and nitrogen atoms were used as substituents. It is typical of the active spiro-thiazines to have alkyl substituents in ortho-and para-position of the benzene ring. Among the investigated spiro-thiazines it is the derivatives with ethyl- and isopropyl-groups in the aril part of the molecules that are the lead-compounds with a high inhibitory ability. We measured the distribution coefficients of the substances in octanol/buffer and hexane/buffer systems and made conclusions about the ability of the investigated drug-like compounds to penetrate the biological membranes. By using the parabolic model we derived a quadratic equation that allowed us to evaluate quantitatively the inhibitory activity of spiro-thiazines with hydrophobic substituents based on lipophilicity data. We also studied the permeability through the phospholipidic membrane and introduced a correlation equation describing the dependence of the investigated spiro-thiazines activity on the descriptors characterizing the donor acceptor properties. (C) 2014 Elsevier Masson SAS. All rights reserved.
• Solubility and Solution Thermodynamics of Novel Bicyclic Derivatives of 1,3-Selenazine in Biological Relevant Solvents
  作者：Svetlana V. Blokhina、Tatyana V. Volkova、Marina V. Ol’khovich、Angelika V. Sharapova、Alexey N. Proshin、German L. Perlovich

  DOI：10.1021/je500363r

  日期：2014.7.10

  Drug-like N-substituted 1-selena-3-azaspiro[5,5]undec-2-en-2-amine hydrobromides (1:1) have been synthesized. Phenyl, isopropylphenyl, and fluorophenyl substituents were used. The solubility of the obtained compounds in pharmaceutically relevant solvents within the temperature range from (298.15 to 318.15) K has been measured using the isothermal saturation technique. All of the compounds studied appear to have poor solubility of similar to 10(-6) mole fraction in phosphate buffer pH 7.4 and hexane. The solubility values enlarge substantially to similar to 10(-2) and 10(-4) mole fraction, respectively, in octanol and muriatic buffer solution pH 2.0. The solubility of the selenazines in aqueous media was shown to increase as the number of protonated forms grew. The high solubility of the compounds in octanol was found to depend on the formation of intermolecular solvent solute hydrogen bonds. Thermodynamic solubility functions for the substances in the solvents studied have been calculated. The solubility in all of the systems with the predominant enthalpy term of Gibbs energy was proved to increase as the dissolution enthalpy decreased.