[(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] 4-[2-[(1-cyclopropyl-6-fluoro-4-oxo-7-piperazin-1-ylquinoline-3-carbonyl)amino]ethylamino]-4-oxobutanoate

• 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: [(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] 4-[2-[(1-cyclopropyl-6-fluoro-4-oxo-7-piperazin-1-ylquinoline-3-carbonyl)amino]ethylamino]-4-oxobutanoate
• 化学式: C₁₀H₉N₂O₅Pol
• 分子量: 745.9
• InChiKey: KGQXUOXQVZZSBG-RWGQXLQGSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.2
• 重原子数：
  54
• 可旋转键数：
  11
• 环数：
  8.0
• sp3杂化的碳原子比例：
  0.69
• 拓扑面积：
  137
• 氢给体数：
  3
• 氢受体数：
  10

反应信息

• 作为反应物：
  描述：

  D-赤式-鞘氨醇盐酸盐 、 [(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] 4-[2-[(1-cyclopropyl-6-fluoro-4-oxo-7-piperazin-1-ylquinoline-3-carbonyl)amino]ethylamino]-4-oxobutanoate 以 四氢呋喃 为溶剂， 反应 10.0h， 生成 N-乙酰基神经鞘氨醇
  参考文献：
  名称：

  手性组合制剂和独特的神经酰胺抑制鞘磷脂合成酶的生物学评估。

  摘要：

  手性生物活性化合物的对映异构体或非对映异构体通常表现出不同的生物学和毒理学性质。在这里，我们报告了鞘氨醇的四种立体异构体的有效合成，以及通过固相活化树脂酯的组合化学，将独特的手性神经酰胺衍生化。此外，为了测试神经酰胺的立体化学的有效性，我们证明了在手性独特神经酰胺存在下基于神经鞘磷脂合成酶抑制的细胞测定，这表明此类文库将是生物活性合成分子的丰富来源。

  DOI：

  10.1002/chir.23179
• 作为产物：
  描述：

  N-(2-aminoethyl)-1-cyclopropyl-6-fluoro-1,4-dihydro-4-oxo-7-(1-piperazinyl)quinoline-3-carboxamide 、 dihydrotestosterone hemisuccinate 在 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 作用下， 以 甲醇 、 水 为溶剂， 反应 72.0h， 以70%的产率得到[(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] 4-[2-[(1-cyclopropyl-6-fluoro-4-oxo-7-piperazin-1-ylquinoline-3-carbonyl)amino]ethylamino]-4-oxobutanoate
  参考文献：
  名称：

  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

  摘要：

  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.

  DOI：

  10.1007/s00706-010-0263-y

文献信息

• Solid phase combinatorial synthesis of a xanthone library using click chemistry and its application to an embryonic stem cell probe
  作者：Krishna Kanta Ghosh、Hyung-Ho Ha、Nam-Young Kang、Yogeswari Chandran、Young-Tae Chang

  DOI：10.1039/c1cc11962a

  日期：——

  We report the first solid phase synthesis of a xanthone library CX and its application to embryonic stem cell probe development. The CX library was further derivatised with an activated ester resin to provide an acetylated CX (CXAC) library. Screening of these libraries led to the discovery of a novel fluorescent mESC probe, CDb8.

  我们报告了x吨酮库CX的第一个固相合成及其在胚胎干细胞探针开发中的应用。CX库进一步用活化的酯树脂衍生化，以提供乙酰化的CX（CXAC）库。这些文库的筛选导致发现新型荧光mESC探针CDb8。
• 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.
• Chiral combinatorial preparation and biological evaluation of unique ceramides for inhibition of sphingomyelin synthase
  作者：Sajeer Koolath、Yuta Murai、Yoshiko Suga、Kenji Monde

  DOI：10.1002/chir.23179

  日期：2020.3

  Enantiomers or diastereomers of chiral bioactive compounds often exhibit different biological and toxicological properties. Here, we report the efficient synthesis of four stereoisomers of sphingosine and derivatization of unique chiral ceramides through a combinatorial chemistry by solid‐phase activated resin ester. In addition, to test the effectivity of stereochemistry of ceramide, we demonstrated

  手性生物活性化合物的对映异构体或非对映异构体通常表现出不同的生物学和毒理学性质。在这里，我们报告了鞘氨醇的四种立体异构体的有效合成，以及通过固相活化树脂酯的组合化学，将独特的手性神经酰胺衍生化。此外，为了测试神经酰胺的立体化学的有效性，我们证明了在手性独特神经酰胺存在下基于神经鞘磷脂合成酶抑制的细胞测定，这表明此类文库将是生物活性合成分子的丰富来源。