3β-acetoxy-5α-cholestan-6-one | 18642-27-8

• 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: 3β-acetoxy-5α-cholestan-6-one
• 英文别名: 3β-acetoxy-cholestan-6-one；3β-acetoxycholestan-6-one；3β-acetoxycholest-6-one；6-Ketocholestan-3β-ol Acetate；[(3S,8S,9S,10R,13R,14S,17R)-10,13-dimethyl-17-[(2R)-6-methylheptan-2-yl]-6-oxo-1,2,3,4,5,7,8,9,11,12,14,15,16,17-tetradecahydrocyclopenta[a]phenanthren-3-yl] acetate
• CAS: 18642-27-8
• 化学式: C₂₉H₄₈O₃
• 分子量: 444.698
• InChiKey: QGGRDHGCNNAWIE-PSQVSWQYSA-N

物化性质

• 熔点：
  128-129 °C
• 沸点：
  513.9±33.0 °C(predicted)
• 密度：
  1.02±0.1 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  8.3
• 重原子数：
  32
• 可旋转键数：
  7
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.93
• 拓扑面积：
  43.4
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  3β-acetoxy-5α-cholestan-6-one 在 吡啶 、 盐酸羟胺 作用下， 反应 5.0h， 以76%的产率得到3β-acetoxy-6-hydroxyiminocholestane
  参考文献：
  名称：

  Synthesis of spermidinylcholestanol and spermidinylcholesterol, squalamine analogues

  摘要：

  Several novel squalamine-related polyaminosterols are reported. The synthesis of 7alpha-N-[3N-(4-aminobutyl)aminopropyl]aminocholestanol I, 6alpha-N-[3N-(4-aminobutyl)aminopropyl]aminocholestanol II, 7alpha and 7beta-N-[3N-(4-aminobutyl)aminopropyl]aminocholesterol (III and IV), was accomplished from cholesterol, they provide the first examples in which spermidine is introduced in the B steroidal ring. These molecules showed comparable antibacteria and fungi activities to squalamine, and were cytotoxic on a human non-small cell bronchopulmonary carcinoma line (NSCLC-N6). Therefore, these molecules with antibiotic and cytotoxic activities are promising for immune-compromised patients in cancer chemotherapy. (C) 2004 Elsevier Ltd. All fights reserved.

  DOI：

  10.1016/j.tet.2004.09.055
• 作为产物：
  描述：

  6-硝基胆固醇乙酸酯 在 溶剂黄146 、 锌 作用下， 生成 3β-acetoxy-5α-cholestan-6-one
  参考文献：
  名称：

  类固醇的噻唑烷酮衍生物的合成及生物学评价

  摘要：

  甾体噻唑烷酮衍生物是通过类固醇的多步反应制备的。它是由甾族硫半脲与溴乙酸乙酯在二恶烷中制得的。通过使硫代氨基脲与甾族酮反应制备甾族硫代氨基脲。这些化合物的结构已通过IR（1）进行了阐明。通过元素分析证实了1 H NMR，Fab质谱及其纯度。通过圆盘扩散测定法评估了这些化合物对两种革兰氏阳性细菌和两种革兰氏阴性细菌的抗菌活性，然后确定了化合物的最小抑菌浓度（MIC）。结果表明，与两种细菌（革兰氏阳性和革兰氏阴性）的甾体硫代半碳酰胺衍生物相比，甾体噻唑烷酮衍生物具有更好的抑制生长的作用。与标准药物阿莫西林相比，化合物7和8是更好的抗菌剂。

  DOI：

  10.1016/j.ejmech.2008.09.004

文献信息

• Synthesis and<i>In Vitro</i>Antibacterial Activity of Novel Steroidal (6R)-Spiro-1,3,4-thiadiazoline Derivatives
  作者：Salman A. Khan、Abdullah M. Asiri

  DOI：10.1002/jhet.1014

  日期：2012.11

  Novel steroidal (6R)‐spiro‐1,3,4‐thiadiazoline derivatives were synthesized by the cyclization of steroidal thiosemicarbazones with acetic anhydride, screened in vitro against antibacterial activity using disc‐diffusion method and the minimum inhibitory concentration. The results showed that steroidal thiadiazoline derivatives exhibited better antibacterial activity than the steroidal thiosemicarbazone

  新型甾体（6R）-螺环-1,3,4-噻二唑啉衍生物是通过甾体硫代半氨基甲酮与乙酸酐的环化反应合成的，采用圆盘扩散法和最小抑菌浓度体外筛选了其抗菌活性。结果表明，甾体噻二唑啉衍生物比甾体硫半碳carb酮衍生物表现出更好的抗菌活性。甾体噻二唑啉环3β位上的氯和乙酰氧基取代基增加了抗菌活性。在所有化合物中，化合物7和8与各自的药物阿莫西林相比，它们被发现是两种细菌（革兰氏阳性和革兰氏阴性）的更好抑制剂。所有合成的化合物都通过红外，1 H-NMR，13 C-NMR质谱，元素分析等光谱学方法进行了很好的表征，并对它们的立体化学进行了讨论。
• Cadmium chloride–magnesium–water: a new system for regioselective transformation of conjugated nitroalkenes to ketocompounds; conversion of 6-nitro-Δ⁵-steroids to 6-ketosteroids
  作者：Manobjyoti Bordoloi

  DOI：10.1039/c39930000922

  日期：——

  Reaction of 6-nitro-Δ5-steroids and nitroalkenes in tetrahydrofuran with CdCl2–Mg–H2O furnished 6-ketosteroids and ketocompounds, respectively, in good yield.

  的反应6-硝基Δ 5个-steroids和硝基烯烃在四氢呋喃中与氯化镉2 -Mg-H 2 ö布置-6-酮类固醇和ketocompounds分别以良好的收率。
• Microwave-assisted MgO NP catalyzed one-pot multicomponent synthesis of polysubstituted steroidal pyridines
  作者：Anam Ansari、Abad Ali、Mohd Asif、Shamsuzzaman Shamsuzzaman

  DOI：10.1039/c7nj03742b

  日期：——

  The present study reports a highly efficient and green synthetic route for the synthesis of steroidal pyridines. The synthetic methodology involves a microwave-assisted one-pot multicomponent reaction using MgO NPs as a heterogeneous, mild and reusable catalyst. The synthesized MgO NPs were characterized by FTIR, TGA/DTA and XRD analyses. The remarkable features of this protocol include simple operational

  本研究报告了合成甾族吡啶的高效和绿色合成路线。合成方法涉及使用MgO NPs作为异质，温和且可重复使用的催化剂的微波辅助单锅多组分反应。通过FTIR，TGA / DTA和XRD分析对合成的MgO纳米颗粒进行了表征。该方案的显着特点包括操作步骤简单，反应曲线更短，反应条件温和，化学废物最少以及经济可行性。催化剂的可回收性和高收率的产品使该方法成为可持续的替代方法。
• Synthesis of steroidal thiazolidinones as antibacterial agents based on the in vitro and quantum chemistry calculation
  作者：Salman A. Khan、Abdullah M. Asiri、Kamlesh Sharma

  DOI：10.1007/s00044-012-0155-2

  日期：2013.4

  Steroidal thiazolidinone derivatives were prepared from the reaction of steroidal thiosemicarbazones with ethyl bromoacetate in dioxane. Steroidal thiosemicarbazones were prepared by reacting thiosemicarbazide with steroidal ketones. The structures of these compounds were elucidated by IR, (HNMR)-H-1, (CNMR)-C-13, and mass spectral study, and their purities were confirmed by elemental analyses. The antibacterial activities of these compounds were evaluated by the disk diffusion assay against two Gram-positive and two Gram-negative bacteria, and then the minimum inhibitory concentration of compounds were determined. The results showed that steroidal thiazolidinone derivatives are better in inhibiting growth as compared with steroidal thiosemicarbazone derivatives of both types of the bacteria. Compounds 7 and 8 are better antibacterial agents as compared with standard drug, Amoxicillin. Based on the quantum chemistry calculation at the DFT/6-31G* level, the frontier molecular orbitals and electrostatic potential of compounds 7 and 8 were also discussed.
• Saikia, Anil K.; Barua, Nabin C.; Sharma, Ram P., Journal of Chemical Research - Part S, 1996, # 2, p. 124 - 125
  作者：Saikia, Anil K.、Barua, Nabin C.、Sharma, Ram P.、Ghosh, Anil C.

  DOI：——

  日期：——