dihydrotestosterone hemisuccinate | 55115-27-0

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 类固醇和类固醇衍生物
• 英文名称: dihydrotestosterone hemisuccinate
• 英文别名: dihydrotestosterone 17β-succinate；succinic acid mono-(3-oxo-5α-androstan-17β-yl ester)；Bernsteinsaeure-mono-(3-oxo-5α-androstan-17β-ylester)；DHT half ester of succinic acid；4-[[(5S,8R,9S,10S,13S,14S,17S)-10,13-dimethyl-3-oxo-1,2,4,5,6,7,8,9,11,12,14,15,16,17-tetradecahydrocyclopenta[a]phenanthren-17-yl]oxy]-4-oxobutanoic acid
• CAS: 55115-27-0
• 化学式: C₂₃H₃₄O₅
• 分子量: 390.52
• InChiKey: XFNYGKWBCJHCQE-XMTZKCFKSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.7
• 重原子数：
  28
• 可旋转键数：
  5
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.87
• 拓扑面积：
  80.7
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  dihydrotestosterone hemisuccinate 在 吡啶 、 氯化亚砜 作用下， 反应 6.0h， 生成 dihydrotestosterone ester of N-(3-carboxypropanoyl)-β-phenyl-α-alanine
  参考文献：
  名称：

  Acylation of steroid alcohols with 3-carboxypropanamido acids

  摘要：

  DOI：

  10.1007/bf00579074
• 作为产物：
  描述：

  succinic acid mono-(3β-hydroxy-androsten-(5)-yl-(17β)-ester) 在 1,4-二氧六环 、 chromium(VI) oxide 、 溶剂黄146 、 铂 作用下， 生成 dihydrotestosterone hemisuccinate
  参考文献：
  名称：

  ÜberSteroide和性激素。（70.米特隆）。二氢-睾丸激素-伯恩斯坦斯-厄尔-哈伯斯特

  摘要：

  DOI：

  10.1002/hlca.194102401139

文献信息

• Cancer specific radiolabeled conjugates regulated by the cell cycle for the treatment and diagnosis of cancer
  申请人：Baranowska-Kortylewicz Janina

  公开号：US20050069495A1

  公开（公告）日：2005-03-31

  Radiolabeled conjugates are disclosed which have a component that is effective to target tumor cells, which cells selectively take up and degrade the conjugate, thereby delivering to the tumor cell nucleus a radioisotope capable of being incorporated into the nuclear material, so as to produce a cytotoxic effect and/or to render the cell detectable by radioimaging.

  揭示了具有一种有效靶向肿瘤细胞的成分的放射性标记结合物，这些细胞选择性地吸收和降解结合物，从而将能够被核物质吸收的放射性同位素传递至肿瘤细胞核，以产生细胞毒作用和/或使细胞可通过放射成像检测。
• Synthesis of a dihydrotestosterone–ciprofloxacin conjugate: relationship between descriptors logP, π, R m , and V m and its antibacterial activity in S. aureus and E. coli
  作者：Lauro Figueroa-Valverde、Francisco Díaz-Cedillo、Abelardo Camacho-Luis、Maria López Ramos、Elodia Garcia Cervera

  DOI：10.1007/s00706-010-0263-y

  日期：2010.3

  In this work a dihydrotestosterone-ciprofloxacin conjugate was synthesized. The route involved preparation of a ciprofloxacin-ethylenediamine derivative by the reaction of ciprofloxacin with ethylenediamine using a carbodiimide or boric acid as catalysts. Additionally, the ciprofloxacin derivative was bound to dihydrotestosterone hemisuccinate to form the dihydrotestosterone-ciprofloxacin conjugate in the presence of a carbodiimide. The antibacterial activity of dihydrotestosterone-ciprofloxacin, as well as ciprofloxacin-ethylenediamine and ciprofloxacin, was evaluated in vitro on S. aureus and E. coli using the dilution method and the minimum inhibitory concentration. To delineate the structural chemical requirements of the compounds ciprofloxacin, ciprofloxacin-ethylenediamine and dihydrotestosterone-ciprofloxacin conjugate as antibacterial agents on S. aureus and E. coli, other parameters such as the descriptors logP, pi, R-m, and V-m were calculated. The results showed that bacterial growth of the microorganisms studied was inhibited by ciprofloxacin, ciprofloxacin-ethylenediamine and dihydrotestosterone-ciprofloxacin in a dose-dependent manner. These data suggest that functional groups involved in the structure of the studied compounds are specific for their antibacterial activity.
• Radiolabeled 5-Iodo-3′-<i>O</i>-(17β-succinyl-5α-androstan-3-one)-2′-deoxyuridine and Its 5′-Monophosphate for Imaging and Therapy of Androgen Receptor-Positive Cancers: Synthesis and Biological Evaluation
  作者：Zbigniew P. Kortylewicz、Jessica Nearman、Janina Baranowska-Kortylewicz

  DOI：10.1021/jm9005803

  日期：2009.8.27

  High levels of androgen receptor (AR) are often indicative of recurrent, advanced, or metastatic cancers. These conditions are also characterized by a high proliferative fraction. 5-Radioiodo-3'-O-(17 beta-succinyl-5 alpha-androstan-3-one)-2'-deoxyuridine 8 and 5-radioiodo-3'-O-(17 beta-succinyl-5 alpha-androstan-3-one)-2'-deoxyuridin-5'-yl monophosphate 13 target AR. They are also degraded intracellularly to 5-radioiodo-2'-deoxyuridine 1 and its monophosphate 20. respectively, which can participate in the DNA synthesis. Both drugs were prepared at the no-carrier-added level. Precursors and methods are readily adaptable to radiolabeling with various radiohalides suitable for SPECT and PET imaging, its well as endoradiotherapy, In vitro and in vivo studies confirm the AR-dependent interactions. Both drugs bind to sex hormone binding globulin. This binding significantly improves their stability in serum. Biodistribution and imaging studies show preferential uptake and retention of 8 and 13 in ip xenografts of human ovarian adenocarcinoma cells NIH:OVCAR-3, which over express A R. When these drugs are administered at therapeutic dose levels, a significant tumor growth arrest is observed.
• Synthesis and androgen receptor binding of dihydrotestosterone hemisuccinate homologs
  作者：Mark E. Stobaugh、Robert T. Blickenstaff

  DOI：10.1016/0039-128x(90)90041-9

  日期：1990.6

  Dihydrotestosterone-succinyl-agarose is the most common form of androgen affinity column. To investigate the effect of variation in the number of methylene groups between the ester and amide functions, a homologous series, varying the number of methylenes between the functional groups, has been synthesized and evaluated. In addition, since structure studies show 17 alpha-methyldihydrotestosterone binds with high affinity, a 17 alpha-carboxymethyl ligand (3) was studied. Relative binding affinities of the dicarboxylates (assayed as the n-butyl amides) range from 0.003 to 0.044 (dihydrotestosterone = 1.00), while there was no detectable binding for 3. Only the suberate binds better than the much-used succinate, and it would be a likely candidate for an affinity ligand.
• Acylation of steroid alcohols with 3-carboxypropanamido acids
  作者：L. N. Volovel'skii、I. A. Rastrepina、N. V. Popova、V. N. Koryukina、S. P. Kustova

  DOI：10.1007/bf00579074

  日期：1985.9