cholest-5-en-3β-yl L-histidinate | 120032-74-8

• 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: cholest-5-en-3β-yl L-histidinate
• CAS: 120032-74-8
• 化学式: C₃₃H₅₃N₃O₂
• 分子量: 523.803
• InChiKey: DKSUUGOYUBRYHW-FWRFMQKPSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.23
• 重原子数：
  38.0
• 可旋转键数：
  9.0
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.82
• 拓扑面积：
  81.0
• 氢给体数：
  2.0
• 氢受体数：
  4.0

反应信息

• 作为产物：
  描述：

  cholest-5-en-3β-yl Nα,Nτ-bis(tert-butoxycarbonyl)-L-histidinate 在 三氟乙酸 作用下， 以 二氯甲烷 为溶剂， 反应 1.0h， 以84%的产率得到cholest-5-en-3β-yl L-histidinate
  参考文献：
  名称：

  Platinum(II) complexes with steroidal esters of l-methionine and l-histidine: Synthesis, characterization and cytotoxic activity

  摘要：

  Twelve steroidal platinum(II) complexes were synthesized by reaction of potassium tetrachloroplatinate with steroidal esters of L-methionine and L-histidine. The steroidal esters coordinated as bidentate ligands via S and N donor atoms of L-methionine and via two N donor atoms of L-histidine. Cholesterol, cholestanol, diosgenine, pregnenolone, dehydroepiandrosterone, testosterone, estrone, and estradiol were used as the steroidal compounds. The esters and complexes prepared were characterized by infrared, mass, and H-1 NMR spectroscopy and elemental analysis. Platinum complexes were tested for in vitro cytotoxicity against several cancer cell lines: T-lymphoblastic leukemia CEM, breast carcinoma MCF-7, lung carcinoma A-549, multiple myeloma RPMI 8226, and one normal cell line human. broblast BJ. (C) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2008.02.003

文献信息

• Synthesis and characterisation of steroidal inhibitors of α-amylase, α-glucosidase and oxidative species
  作者：Bamidele J. Okoli、Mthunzi Fanyana、James D. Habila、Ayo G. Rachael、Iloegbulam G. Ndukwe、Olugbemi T. Olaniyan、Johannes S. Modise

  DOI：10.3233/mnm-190333

  日期：2019.12.3

  BACKGROUND: Management of cellular metabolism and blood glucose levels are significant in the treatment of diabetes mellitus and oxidative diseases. Consequently, steroid and peptide hormone-based drugs such as methylprednisolone and insulin have been the most effective and safe methods of treatment.OBJECTIVE: Our study investigated the digestive enzymes and oxidative species inhibitory potentials of seven derived biologically important steroids.METHODS: Syntheses of the steroidal inhibitors (SIs) were accomplished by functional group transformations. Characterisation of SIs was achieved by spectroscopic techniques; followed by in-vitro enzyme and oxidative suppression studies.RESULTS: NMR data revealed the presence of a steroid backbone, azomethine, carbonyl, and oxymethine peaks while the vibrational bands were further confirmed by the FTIR. The enzyme suppression activities of the SIs were influenced by the presence of histidine residue and free proton groups. However, the antioxidant activities were solely dependent on the free proton groups on the steroid backbone or the number of the histidine side chain. SIs [3, 4, and 6] exhibited a potent inhibitory effect on the enzyme activities compared to SIs [1, 2, 5, and 7], while a potent antioxidant activity was reported by SI [5].CONCLUSIONS: Generally, SIs with hydroxyl and alpha-amino acid functionalities have a strong affinity for the enzyme active site than the substrate; hence, the hydrolysis of the alpha-1,4-glycosidic bonds of saccharide was hindered. In vivo administration of SIs [3, 4, and 6] should take into cognizance the suppression effect at doses <= 939.49 mu g/mL as well as the potential to induce abnormal bacterial fermentation of undigested carbohydrates in the colon at high concentration.