cholest-5-ene-3,7-dione | 17974-82-2

• 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-ene-3,7-dione
• 英文别名: 3,7-diketocholestene；7-Oxo-cholestenone；(8S,9S,10R,13R,14S,17R)-10,13-dimethyl-17-[(2R)-6-methylheptan-2-yl]-2,4,8,9,11,12,14,15,16,17-decahydro-1H-cyclopenta[a]phenanthrene-3,7-dione
• CAS: 17974-82-2
• 化学式: C₂₇H₄₂O₂
• 分子量: 398.629
• InChiKey: SQPQMCUHNOULQL-KRQCSNJGSA-N

物化性质

• 熔点：
  91 °C
• 沸点：
  513.7±29.0 °C(Predicted)
• 密度：
  1.02±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  7.1
• 重原子数：
  29
• 可旋转键数：
  5
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.85
• 拓扑面积：
  34.1
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  cholest-5-ene-3,7-dione 在 cerium(III) chloride 、 硼氘化钠 作用下， 以 四氢呋喃 、 甲醇 为溶剂， 反应 1.0h， 以90%的产率得到[3α,7α-²H2]-cholest-5-ene-3β,7β-diol
  参考文献：
  名称：

  Synthesis of deuterium and tritium labelled 7-hydroxy- and 7-oxosterols

  摘要：

  Deuterium and tritium 3,7-bis-labelled 7-hydroxysterols 3 - 5 were prepared by reduction of the 3,7-dioxosterols 1, 2 with (NaBH4)-H-2 and (NaBH4)-H-3. Regioselective oxidation of the deuterium 3,7-bis-labelled 7-hydroxysterols 3, 4 with CrO3/DMP led to the 3-labelled 7-oxosterols 6, 7. The 3,7-dioxosterols 1, 2 were synthesized starting from cholesterol and beta-sitosterol.

  DOI：

  10.1002/(sici)1099-1344(199804)41:4<329::aid-jlcr82>3.0.co;2-x
• 作为产物：
  描述：

  胆固醇 在 chromium(VI) oxide 、 过氧乙酸 、 2,4-dimethyl-2,4-pentanediol 作用下， 以 四氯化碳 、 二氯甲烷 为溶剂， 反应 48.0h， 以45%的产率得到cholest-5-ene-3,7-dione
  参考文献：
  名称：

  Synthesis and antifungal activity of oxygenated cholesterol derivatives

  摘要：

  A series of oxygenated cholesterol derivatives were prepared from new synthetic methods and evaluated for their in vitro antimicrobial properties against human pathogens. The activity was highly dependent on the structure of the different compounds involved. The best results were obtained with hydroxy ketones 2, 4 and 5 and diketone 7 exhibiting activities against S. cerevisiae (ATCC 28383) and Candida albicans (CIP 1663-86). For example, compound 2 exhibited high activities against C. albicans (CIP 1663-86) and Amphotericine B and miconazole resistant strain C. albicans (CIP 1180-79) at a concentration of 1.5 mu g/mL. (c) 2005 Elsevier Inc. All rights reserved.

  DOI：

  10.1016/j.steroids.2005.06.007

文献信息

• Squalamine and Aminosterol Mimics Inhibit the Peptidoglycan Glycosyltransferase Activity of PBP1b
  作者：Adrien Boes、Jean Michel Brunel、Adeline Derouaux、Frédéric Kerff、Ahmed Bouhss、Thierry Touze、Eefjan Breukink、Mohammed Terrak

  DOI：10.3390/antibiotics9070373

  日期：——

  Peptidoglycan (PG) is an essential polymer of the bacterial cell wall and a major antibacterial target. Its synthesis requires glycosyltransferase (GTase) and transpeptidase enzymes that, respectively, catalyze glycan chain elongation and their cross-linking to form the protective sacculus of the bacterial cell. The GTase domain of bifunctional penicillin-binding proteins (PBPs) of class A, such as

  肽聚糖（PG）是细菌细胞壁的主要聚合物，也是主要的抗菌靶标。它的合成需要糖基转移酶（GTase）和转肽酶，它们分别催化聚糖链的延长及其交联形成细菌细胞的保护囊。A类双功能青霉素结合蛋白（PBP）的GTase域，例如大肠杆菌PBP1b，属于GTase 51家族。这些酶在PG合成中起着至关重要的作用，并且它们被莫诺霉素的特异性抑制作用导致细菌细胞死亡。在这项工作中，我们报告氨基固醇角鲨胺和模拟化合物呈现出意想不到的作用方式，该作用方式包括抑制模型酶PBP1b的GTase活性。另外，在荧光各向异性测定中，所选化合物能够从活性位点特异性置换脂质II，表明它们起竞争性抑制剂的作用。
• Synthesis and antifungal activity of cholesterol-hydrazone derivatives
  作者：Céline Loncle、Jean Michel Brunel、Nicolas Vidal、Michel Dherbomez、Yves Letourneux

  DOI：10.1016/j.ejmech.2004.07.005

  日期：2004.12

  A series of hydrazones synthesized from various cholesterol derivatives were evaluated for their in vitro antimicrobial properties against human pathogens. The activity was highly dependent on the structure of the different compounds involved. The best results have been obtained with tosylhydrazone cholesterol derivatives 8 and 9 exhibiting activities against Candida albicans (CIP 1663-80) at a concentration of 1.5 mug/ml. (C) 2004 Elsevier SAS. All rights reserved.
• Synthesis and antifungal activity of oxygenated cholesterol derivatives
  作者：J BRUNEL、C LONCLE、N VIDAL、M DHERBOMEZ、Y LETOURNEUX

  DOI：10.1016/j.steroids.2005.06.007

  日期：2005.12.1

  A series of oxygenated cholesterol derivatives were prepared from new synthetic methods and evaluated for their in vitro antimicrobial properties against human pathogens. The activity was highly dependent on the structure of the different compounds involved. The best results were obtained with hydroxy ketones 2, 4 and 5 and diketone 7 exhibiting activities against S. cerevisiae (ATCC 28383) and Candida albicans (CIP 1663-86). For example, compound 2 exhibited high activities against C. albicans (CIP 1663-86) and Amphotericine B and miconazole resistant strain C. albicans (CIP 1180-79) at a concentration of 1.5 mu g/mL. (c) 2005 Elsevier Inc. All rights reserved.
• Synthesis of deuterium and tritium labelled 7-hydroxy- and 7-oxosterols
  作者：H. Schabdach、J. Schröder、K. Seifert

  DOI：10.1002/(sici)1099-1344(199804)41:4<329::aid-jlcr82>3.0.co;2-x

  日期：1998.4

  Deuterium and tritium 3,7-bis-labelled 7-hydroxysterols 3 - 5 were prepared by reduction of the 3,7-dioxosterols 1, 2 with (NaBH4)-H-2 and (NaBH4)-H-3. Regioselective oxidation of the deuterium 3,7-bis-labelled 7-hydroxysterols 3, 4 with CrO3/DMP led to the 3-labelled 7-oxosterols 6, 7. The 3,7-dioxosterols 1, 2 were synthesized starting from cholesterol and beta-sitosterol.