DTIB | 300627-68-3

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑烷类
• 英文名称: DTIB
• 英文别名: 4-[3-(4-Hydroxy-butyl)-4,4-dimethyl-5-oxo-2-thioxo-imidazolidin-1-yl]-2-iodo-benzonitrile；4-[3-(4-hydroxybutyl)-4,4-dimethyl-5-oxo-2-sulfanylideneimidazolidin-1-yl]-2-iodobenzonitrile
• CAS: 300627-68-3
• 化学式: C₁₆H₁₈IN₃O₂S
• 分子量: 443.308
• InChiKey: COLBUQNTUDHMHF-UHFFFAOYSA-N

物化性质

• 沸点：
  538.0±60.0 °C(Predicted)
• 密度：
  1.69±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  23
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.44
• 拓扑面积：
  99.7
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  DTIB 在 硫酸氢铵 、 sodium iodide 作用下， 生成 4-[3-(4-hydroxybutyl)-4,4-dimethyl-5-oxo-2-sulfanylideneimidazolidin-1-yl]-2-(125I)iodanylbenzonitrile
  参考文献：
  名称：

  Dort, M. E. Van; Jung, Y.-W.; Sherman, P. S., Journal of Labelled Compounds and Radiopharmaceuticals, 2001, vol. 44, p. S327 - S329

  摘要：

  DOI：
• 作为产物：
  描述：

  2-碘-4-硝基苯甲酸 在 盐酸 、 ammonium hydroxide 、 氯化亚砜 、 三乙胺 、 tin(ll) chloride 作用下， 以 四氢呋喃 、 乙醇 、 水 为溶剂， 反应 15.0h， 生成 DTIB
  参考文献：
  名称：

  Design, Synthesis, and Pharmacological Characterization of 4-[4,4-Dimethyl-3-(4-hydroxybutyl)-5-oxo-2-thioxo-1-imidazolidinyl]- 2-iodobenzonitrile as a High-Affinity Nonsteroidal Androgen Receptor Ligand

  摘要：

  4-[4,4-Dimethyl-3-(4-hydroxybutyl)-5-oxo-2-thioxo-1-imidazolidinyl]-2-trifluoromethylbenzonitrile (RU 59063) is a prototype of a new class of high-affinity nonsteroidal androgen receptor (AR) ligands. The search for a radioiodinated AR ligand prompted us to synthesize 4-[4,4-dimethyl-3-(4-hydroxybutyl)-5-oxo-2-thioxo-1-imidazolidinyl]-2-iodobenzonitrile (DTIB) wherein the trifluoromethyl group of RU 59063 was substituted with the similarly hydrophobic iodine atom. DTIB displayed subnanomolar binding affinity (K-i = 0.71 +/- 0.22 nM) for the rat AR in competitive binding assays. Additionally, DTIB demonstrated potent agonist activity, comparable to that of the natural androgen 5 alpha-dihydrotestosterone (DHT), in a cell-based functional assay (cotransfection assay). DTIB represents a new lead for the development of high-affinity radioiodinated AR radioligands.

  DOI：

  10.1021/jm000163y

文献信息

• Synthesis and structure–activity investigation of iodinated arylhydantoins and arylthiohydantoins for development as androgen receptor radioligands
  作者：Marcian E. Van Dort、Yong-Woon Jung

  DOI：10.1016/j.bmcl.2004.08.031

  日期：2004.11

  A series of side-chain derivatives of the arylhydantoin RU 58841 and the arylthiohydantoin RU 59063, wherein the aromatic trifluoromethyl group was replaced with iodine, was synthesized for possible development as radioiodinated androgon receptor (AR) ligands. Derivatives containing the cyanomethyl, methoxyethyl and propenyl side-chains displayed moderately high affinity (K-i = 20-59 nM) towards the rat AR. Side-chains containing bulky lipophilic groups such as, benzyl and phenylpropyl, were poorly tolerated (K-i > 219 nM). Superior AR binding affinities (0.71 nM < Ki < 11 nM) were displayed by arylhydantoins and arylthiohydantom derivatives containing hydroxybutyl or methyl side-chains. The latter compounds are potential candidates for development as radioiodinated AR ligands. (C) 2004 Elsevier Ltd. All rights reserved.
• Design, Synthesis, and Pharmacological Characterization of 4-[4,4-Dimethyl-3-(4-hydroxybutyl)-5-oxo-2-thioxo-1-imidazolidinyl]- 2-iodobenzonitrile as a High-Affinity Nonsteroidal Androgen Receptor Ligand
  作者：Marcian E. Van Dort、Diane M. Robins、Bess Wayburn

  DOI：10.1021/jm000163y

  日期：2000.8.1

  4-[4,4-Dimethyl-3-(4-hydroxybutyl)-5-oxo-2-thioxo-1-imidazolidinyl]-2-trifluoromethylbenzonitrile (RU 59063) is a prototype of a new class of high-affinity nonsteroidal androgen receptor (AR) ligands. The search for a radioiodinated AR ligand prompted us to synthesize 4-[4,4-dimethyl-3-(4-hydroxybutyl)-5-oxo-2-thioxo-1-imidazolidinyl]-2-iodobenzonitrile (DTIB) wherein the trifluoromethyl group of RU 59063 was substituted with the similarly hydrophobic iodine atom. DTIB displayed subnanomolar binding affinity (K-i = 0.71 +/- 0.22 nM) for the rat AR in competitive binding assays. Additionally, DTIB demonstrated potent agonist activity, comparable to that of the natural androgen 5 alpha-dihydrotestosterone (DHT), in a cell-based functional assay (cotransfection assay). DTIB represents a new lead for the development of high-affinity radioiodinated AR radioligands.
• Dort, M. E. Van; Jung, Y.-W.; Sherman, P. S., Journal of Labelled Compounds and Radiopharmaceuticals, 2001, vol. 44, p. S327 - S329
  作者：Dort, M. E. Van、Jung, Y.-W.、Sherman, P. S.、Kuszpit, K. K.

  DOI：——

  日期：——