3β,21-dihydroxy-9β,10α-pregna-5,7-dien-20-one | 86416-32-2

• 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: 3β,21-dihydroxy-9β,10α-pregna-5,7-dien-20-one
• 英文别名: 21-Hydroxy-9beta,10alpha-pregna-5,7-diene-3-ol-20-one；2-hydroxy-1-[(3S,9R,10S,13S,14R,17S)-3-hydroxy-10,13-dimethyl-2,3,4,9,11,12,14,15,16,17-decahydro-1H-cyclopenta[a]phenanthren-17-yl]ethanone
• CAS: 86416-32-2
• 化学式: C₂₁H₃₀O₃
• 分子量: 330.467
• InChiKey: MGYSTOQOSMRLQF-JZUJSFITSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  24
• 可旋转键数：
  2
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.76
• 拓扑面积：
  57.5
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  21-乙酰氧基孕烯醇酮 在 1,3-二溴-5,5-二甲基海因 、 偶氮二异丁腈 、 对甲苯磺酸一水合物 、 四丁基溴化铵 、 potassium carbonate 作用下， 以 四氢呋喃 、 甲醇 、 正己烷 、 苯 为溶剂， 反应 12.67h， 生成 3β,21-dihydroxy-9β,10α-pregna-5,7-dien-20-one 、 1-[(1S,7aR)-4-[(E)-2-[(3S)-3-hydroxy-6-methyl-7,8-dioxabicyclo[4.2.0]octan-1-yl]ethenyl]-7a-methyl-1,2,3,5,6,7-hexahydroinden-1-yl]-2-hydroxyethanone 、 (5Z,7E)-3β,21-dihydroxy-9,10-secopregna-5,7,10(19)-trien-20-one
  参考文献：
  名称：

  3beta,21-dihydroxypregna-5,7-dien-20-one 的合成和光化学转化为显示抗黑色素瘤活性的新型 secosteroid。

  摘要：

  我们合成了 3beta,21-dihydroxypregna-5,7-dien-20-one (21(OH) 7DHP) 并使用 UVB 辐射诱导其光转化为维生素 D (pD)、lumisterol (pL) 和 tachysterol (pT) 的类似物）。产品的数量和特性以及过程的动态取决于 UVB 剂量。主要产品：pD和pT化合物在RP-HPLC色谱后通过UV吸收、MS和NMR光谱进行表征。此外，检测到初级产物的多种氧化衍生物的形成，并且这些衍生物之一被表征为氧化的 21-羟基异速甾醇化合物 (21(OH)oxy-piT)。这些新合成的化合物以剂量依赖性方式抑制人类黑色素瘤细胞的生长，对骨化三醇具有更大或相等的效力。3beta,21-Dihydroxy-9beta,10alpha-pregna-5, 7-dien-20-one (21(OH)pL) 和 21(OH)oxy-piT 对

  DOI：

  10.1016/j.steroids.2010.10.009

文献信息

• Enzymatic Production or Chemical Synthesis and Uses for 5,7-Dienes and UVB Conversion Products Thereof
  申请人：Slominski Andrej

  公开号：US20120258938A1

  公开（公告）日：2012-10-11

  Provided herein are steroidal compounds that are androsta-5,7-dienes or pregna-5,7-dienes and ultraviolet B (UVB) conversion products thereof and cholecalciferol derivatives hydroxylated at one or more of C1, C17, C20, C23, C24, C25, and C26 which includes pharmaceutical, cosmeceutical or nutraceutical compositions of the steroidal compounds as shown in Tables 1A, 2A and 3. Also provided is a method for producing hydroxylated metabolites of cholecalciferol via CYP11A1, CYP24, CYP27A1, or CYP27B1 enzyme systems where the hydroxylase has an activity to hydroxylate position C1 or C20 or other position of the sidechain of a secosteroid or its 5,7-dieneal precursor and the hydroxylated metabolites so produced. Methods are provided for inhibiting proliferation of either a normally or abnormally proliferating cell, for modifying immune activity, or for treating a condition associated with the proliferating or quiescent cell or immune cells by contacting the cell with or administering any of the compounds described herein.

  本文提供的是雄甾-5,7-二烯或孕甾-5,7-二烯及其紫外线B（UVB）转化产物和羟化在C1、C17、C20、C23、C24、C25和C26上的胆钙醇衍生物，其中包括表1A、2A和3中所示的雄甾类化合物的制药、化妆品或营养品组合物。同时，本文还提供了一种通过CYP11A1、CYP24、CYP27A1或CYP27B1酶系统产生羟化代谢产物的方法，其中羟化酶具有羟化分裂素或其5,7-二烯前体的侧链的C1或C20或其他位置的活性，以及由此产生的羟化代谢产物。本文还提供了一种通过接触或给予本文所述的任何化合物来抑制正常或异常增殖细胞的增殖，修饰免疫活性或治疗与增殖或静止细胞或免疫细胞相关的疾病的方法。
• Enzymatic production or chemical synthesis and uses for 5,7-dienes and UVB conversion products thereof
  申请人：Slominski Andrzej

  公开号：US20110118228A1

  公开（公告）日：2011-05-19

  Provided herein are steroidal compounds that are androsta-5,7-dienes or a pregna-5,7-dienes and ultraviolet B (UVB) conversion products thereof which includes pharmaceutical compositions of the steroidal compounds as shown in Tables 1 and 2. Also provided is a method for producing hydroxylated metabolites of cholecalciferol or ergocalciferol via the P450scc (CYP11A1) or CYP27B1 enzyme systems where the hydroxylase has an activity to hydroxylate position C20 of a secosteroid or its 5,7-dieneal precursor and the hydroxylated metabolites so produced. In addition, a method for inhibiting proliferation of either a normally or abnormally proliferating cell by contacting the cell with any of the compounds described herein. A related method is provided of treating a condition associated with the proliferating cell such as a cancer, a skin disorder, a defect in cell differentiation, cosmetic, prophylaxsis, or healthy cell maintenance.

  本文提供的是雄甾-5,7-二烯或孕甾-5,7-二烯及其紫外线B（UVB）转化产物的类固醇化合物，其中包括所示的表1和表2的类固醇化合物的药物组成。此外，还提供了一种通过P450scc（CYP11A1）或CYP27B1酶系统产生维生素D3或维生素D2的羟化代谢产物的方法，其中羟化酶具有羟化一个类固醇的C20位置或其5,7-二烯前体的活性，以及所产生的羟化代谢产物。此外，还提供了一种通过接触任何本文所述的化合物来抑制正常或异常增殖细胞增殖的方法。还提供了一种相关的方法，用于治疗与增殖细胞相关的疾病，例如癌症，皮肤疾病，细胞分化缺陷，美容，预防或维持健康的细胞。
• [EN] ENZYMATIC PRODUCTION OR CHEMICAL SYNTHESIS AND USES FOR 5,7-DIENES AND UVB CONVERSION PRODUCTS THEREOF<br/>[FR] PRODUCTION ENZYMATIQUE OU SYNTHÈSE CHIMIQUE ET UTILISATIONS POUR LES 5,7-DIÈNES ET PRODUITS DE CONVERSION UVB AINSI OBTENUS
  申请人：UNIV TENNESSEE RES FOUNDATION

  公开号：WO2009108388A2

  公开（公告）日：2009-09-03

  Provided herein are steroidal compounds that are androsta-5,7-dienes or a pregna-5,7-dienes and ultraviolet B (UVB) conversion products thereof which includes pharmaceutical compositions of the steroidal compounds. Also provided is a method for producing hydroxylated metabolites of cholecalciferol via the P450scc (CYPl IA 1) or CYP27B 1 enzyme systems and the hydroxylated metabolites so produced. In addition, a method for inhibiting proliferation of either a normally or abnormally proliferating cell by contacting the cell with any of the compounds described herein. A related method is provided of treating a condition associated with the proliferating cell such as a cancer, a skin disorder, a defect in cell differentiation, cosmetic, prophylaxsis, or healthy cell maintenance.
• Synthesis and photochemical transformation of 3β,21-dihydroxypregna-5,7-dien-20-one to novel secosteroids that show anti-melanoma activity
  作者：Michal A. Zmijewski、Wei Li、Jianjun Chen、Tae-Kang Kim、Jordan K. Zjawiony、Trevor W. Sweatman、Duane D. Miller、Andrzej T. Slominski

  DOI：10.1016/j.steroids.2010.10.009

  日期：2011.1

  We have synthesized 3beta,21-dihydroxypregna-5,7-dien-20-one (21(OH) 7DHP) and used UVB radiation to induce its photoconversion to analogues of vitamin D (pD), lumisterol (pL) and tachysterol (pT). The number and character of the products and the dynamics of the process were dependent on the UVB dose. The main products: pD and pT compounds were characterized by UV absorption, MS and NMR spectroscopy

  我们合成了 3beta,21-dihydroxypregna-5,7-dien-20-one (21(OH) 7DHP) 并使用 UVB 辐射诱导其光转化为维生素 D (pD)、lumisterol (pL) 和 tachysterol (pT) 的类似物）。产品的数量和特性以及过程的动态取决于 UVB 剂量。主要产品：pD和pT化合物在RP-HPLC色谱后通过UV吸收、MS和NMR光谱进行表征。此外，检测到初级产物的多种氧化衍生物的形成，并且这些衍生物之一被表征为氧化的 21-羟基异速甾醇化合物 (21(OH)oxy-piT)。这些新合成的化合物以剂量依赖性方式抑制人类黑色素瘤细胞的生长，对骨化三醇具有更大或相等的效力。3beta,21-Dihydroxy-9beta,10alpha-pregna-5, 7-dien-20-one (21(OH)pL) 和 21(OH)oxy-piT 对