(3S,8R,9S,10R,13S,14S,16S)-3,16-二羟基-10,13-二甲基-1,2,3,4,7,8,9,11,12,14,15,16-十二氢环戊烯并[a]菲-17-酮 | 1159-68-8

• 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
• 中文名称: (3S,8R,9S,10R,13S,14S,16S)-3,16-二羟基-10,13-二甲基-1,2,3,4,7,8,9,11,12,14,15,16-十二氢环戊烯并[a]菲-17-酮
• 英文名称: 3β,16β-Dihydroxy-androst-5-en-17-on
• 英文别名: 16β-hydroxydehydroepiandrosterone；3β,16β-dihydroxyandrost-5-en-17-one；16beta-Hydroxydehydroepiandrosterone；(3S,8R,9S,10R,13S,14S,16S)-3,16-dihydroxy-10,13-dimethyl-1,2,3,4,7,8,9,11,12,14,15,16-dodecahydrocyclopenta[a]phenanthren-17-one
• CAS: 1159-68-8
• 化学式: C₁₉H₂₈O₃
• 分子量: 304.43
• InChiKey: QQIVKFZWLZJXJT-HLUDHZFRSA-N

物化性质

• 沸点：
  469.6±45.0 °C(Predicted)
• 密度：
  1.19±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  22
• 可旋转键数：
  0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.84
• 拓扑面积：
  57.5
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (3S,8R,9S,10R,13S,14S,16S)-3,16-二羟基-10,13-二甲基-1,2,3,4,7,8,9,11,12,14,15,16-十二氢环戊烯并[a]菲-17-酮 在 palladium on activated charcoal 氢气 作用下， 以 乙酸乙酯 为溶剂， 生成 16β-hydroxy-5α-androstan-17-one
  参考文献：
  名称：

  甾族邻域酮醇和相关化合物的碳13核磁共振光谱数据。

  摘要：

  报道了在环D处具有邻位氧化功能的31 3β-羟基和乙酰氧基雄烷衍生物的碳-13核磁共振光谱，在C-6处具有和不具有氧化功能。讨论了相对的取代基效应。

  DOI：

  10.1016/0039-128x(91)90077-9
• 作为产物：
  描述：

  去氢表雄酮 在 glucose dehydrogenase 、 2,3,4,5,6-pentahydroxy-hexanal 、 Bacillus megaterium P₄₅₀BM₃ enzyme GV A₁₈₄I variant 作用下， 以 aq. phosphate buffer 为溶剂， 反应 16.0h， 生成 (3S,8R,9S,10R,13S,14S,16S)-3,16-二羟基-10,13-二甲基-1,2,3,4,7,8,9,11,12,14,15,16-十二氢环戊烯并[a]菲-17-酮
  参考文献：
  名称：

  自然启发性扫描甘氨酸诱变P450BM3（CYP102A1）的类固醇的氧化多样化。

  摘要：

  甾族化合物是处方最广泛的药物，被指定用于治疗各种疾病，包括炎症，心脏病和癌症。功能化类固醇的合成方法对于产生用于药物筛选和开发的类固醇剂很重要。但是，由于类固醇中主要存在惰性的脂肪族CH键，因此化学活化具有挑战性。在这里，我们报道了来自巨大芽孢杆菌的稳定，高活性细菌细胞色素P450酶P450BM3（CYP102A1）的工程设计用于雄烯二酮（AD），脱氢表雄酮（DHEA）和睾丸激素（TST）的单羟基和二羟基化作用。为了设计改变的类固醇结合方向，我们比较了野生型P450BM3与类固醇C19-去甲基化酶CYP19A1的结构，其中AD结合在其活性位点，并鉴定了I螺旋和β4链区域，该区域阻止了P450BM3的这种结合方向。在这两个区域的11个残基上扫描甘氨酸诱变会导致以前未报道过P450BM3的类固醇氧化产物。在第二轮诱变中将这些甘氨酸突变结合在一起，形成了一个小的P450BM3变体文库，该变体能够

  DOI：

  10.1021/acscatal.0c02077

文献信息

• Oxa- or azasteroid derivatives
  申请人：Teikoku Hormone Mfg. Co., Ltd.

  公开号：US05519051A1

  公开（公告）日：1996-05-21

  Compounds are described having the formula ##STR1## wherein A denotes C.dbd.O, CH.sub.2, C.dbd.CH.sub.2 or C.dbd.CH-lower alkyl; B denotes O, NH or N-lower alkyl; X does not exist, or denotes C.dbd.O or CH.sub.2 ; n denotes 2 or 3 when X does not exist, or denotes 1 or 2 when X denotes C.dbd.O or CH.sub.2 ; and the broken line between the 1- and 2-positions of the steroid skeleton means that a double bond may optionally exist there. These compounds have an aromatase inhibition action and are useful for prophylaxis or treatment of diseases caused by excess of estrogens, for example, breast cancer, uterine cancer, prostatic hypertrophy, etc.

  化合物的结构式为##STR1##其中A代表C.dbd.O、CH.sub.2、C.dbd.CH.sub.2或C.dbd.CH-较低烷基；B代表O、NH或N-较低烷基；X不存在，或代表C.dbd.O或CH.sub.2；当X不存在时，n代表2或3，或当X代表C.dbd.O或CH.sub.2时，n代表1或2；在类固醇骨架的1-和2-位置之间的虚线表示那里可能存在一个双键。这些化合物具有抑制芳香化酶的作用，可用于预防或治疗由雌激素过多引起的疾病，例如乳腺癌、子宫癌、前列腺肥大等。
• Preparation of 3β,16β-dihydroxyandrost-5-en-17-one: Stabilization of its α-ketolic group toward alkali by formation of a semicarbazone
  作者：Vernon R. Mattox、Albert N. Nelson

  DOI：10.1016/0039-128x(76)90143-4

  日期：1976.6

  Abstract Alkaline hydrolysis of a 16β-acetoxy-17-oxo steroid is accompanied by almost complete rearrangement of the product to a 16-oxo-17β-hydroxy steroid. Hydrolysis can be achieved without rearrangement by 1) formation of a C-17 semicarbazone, 2) alkaline removal of the acetate group, and 3) removal of the semicarbazone group in the presence of pyruvic acid-acetic acid. By employing this technique

  摘要 16β-乙酰氧基-17-氧代类固醇的碱性水解伴随着产物几乎完全重排为16-氧代-17β-羟基类固醇。水解可以在不重排的情况下通过 1) 形成 C-17 缩氨基脲，2) 碱去除乙酸酯基团，和 3) 在丙酮酸-乙酸存在下去除缩氨基脲基团而实现。通过使用该技术，从其二乙酸盐以65%的产率获得标题化合物。
• REMEDY FOR HORMONE-DEPENDENT CANCER
  申请人：KYOWA HAKKO KOGYO CO., LTD.

  公开号：EP1568381A1

  公开（公告）日：2005-08-31

  A therapeutic agent for a hormone-dependent cancer, which comprises (a) a steroid-sulfatase inhibitor and (b) an agent for hormone therapy and/or an agent for chemotherapy, which may be administered together or separately at an interval, is provided. A method for treating a hormone-dependent cancer, which comprises administering (a) a steroid-sulfatase inhibitor and (b) an agent for hormone therapy and/or an agent for chemotherapy together or separately at an interval, is also provided. A steroid-sulfatase inhibitor which is used in combination with an agent for hormone therapy and/or an agent for chemotherapy, and which is administered together therewith or separately therefrom at an interval, is also provided. A kit for treating a hormone-dependent cancer, which comprises a first component comprising (a) a steroid-sulfatase inhibitor and a second component comprising (b) an agent for hormone therapy and/or an agent for chemotherapy, is also provided. A pharmaceutical composition, which comprises (a) a steroid-sulfatase inhibitor and (b) an agent for hormone therapy and/or an agent for chemotherapy, is also provided. Further, use of (a) a steroid-sulfatase inhibitor and (b) an agent for hormone therapy and/or an agent for chemotherapy for the manufacture of a therapeutic agent for a hormone-dependent cancer is provided.

  本发明提供了一种激素依赖性癌症的治疗剂，它包括(a)类固醇硫酸酯酶抑制剂和(b)激素治疗剂和/或化疗剂，这两种药物可以一起给药，也可以间隔一段时间分别给药。还提供了一种治疗激素依赖性癌症的方法，该方法包括(a)类固醇-硫酸酯酶抑制剂和(b)激素治疗制剂和/或化疗制剂，它们可以一起给药，也可以间隔一段时间分别给药。还提供了一种类固醇硫酸酯酶抑制剂，该抑制剂与激素治疗剂和/或化疗剂联合使用，并在一定间隔时间内一起或分开给药。还提供了一种用于治疗激素依赖性癌症的试剂盒，它包括由(a)类固醇硫酸酯酶抑制剂组成的第一组分和由(b)激素治疗剂和/或化疗剂组成的第二组分。还提供了一种药物组合物，它包含(a)类固醇硫酸酯酶抑制剂和(b)激素治疗剂和/或化疗剂。此外，还提供了使用(a)类固醇硫酸酯酶抑制剂和(b)激素治疗剂和/或化疗剂制造激素依赖性癌症治疗剂的方法。
• Remedy for hormone-dependent cancer
  申请人：Shiotsu Yukimasa

  公开号：US20060035875A1

  公开（公告）日：2006-02-16

  A therapeutic agent for a hormone-dependent cancer, which comprises (a) a steroid-sulfatase inhibitor and (b) an agent for hormone therapy and/or an agent for chemotherapy, which may be administered together or separately at an interval, is provided. A method for treating a hormone-dependent cancer, which comprises administering (a) a steroid-sulfatase inhibitor and (b) an agent for hormone therapy and/or an agent for chemotherapy together or separately at an interval, is also provided. A steroid-sulfatase inhibitor which is used in combination with an agent for hormone therapy and/or an agent for chemotherapy, and which is administered together therewith or separately therefrom at an interval, is also provided. A kit for treating a hormone-dependent cancer, which comprises a first component comprising (a) a steroid-sulfatase inhibitor and a second component comprising (b) an agent for hormone therapy and/or an agent for chemotherapy, is also provided. A pharmaceutical composition, which comprises (a) a steroid-sulfatase inhibitor and (b) an agent for hormone therapy and/or an agent for chemotherapy, is also provided. Further, use of (a) a steroid-sulfatase inhibitor and (b) an agent for hormone therapy and/or an agent for chemotherapy for the manufacture of a therapeutic agent for a hormone-dependent cancer is provided.
• US4898694A
  申请人：——

  公开号：US4898694A

  公开（公告）日：1990-02-06