16α-bromoandrost-5-en-17-one | 112859-75-3

• 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: 16α-bromoandrost-5-en-17-one
• 英文别名: 16α-bromo-5-androsten-17-one；16alpha-Bromo-5-androsten-17-one；(8R,9S,10R,13S,14S,16R)-16-bromo-10,13-dimethyl-1,2,3,4,7,8,9,11,12,14,15,16-dodecahydrocyclopenta[a]phenanthren-17-one
• CAS: 112859-75-3
• 化学式: C₁₉H₂₇BrO
• 分子量: 351.327
• InChiKey: LXSRYCCKGWATML-NBBHSKLNSA-N

物化性质

• 沸点：
  419.7±45.0 °C(Predicted)
• 密度：
  1.28±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  5.5
• 重原子数：
  21
• 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：
  17.1
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  16α-bromoandrost-5-en-17-one 在 盐酸 、 sodium hydroxide 作用下， 以 吡啶 、 (2S)-N-methyl-1-phenylpropan-2-amine hydrate 、 水 为溶剂， 生成 16α-hydroxy-5-androsten-17-one
  参考文献：
  名称：

  Method for prophylaxis of obesity

  摘要：

  ##STR1## 作为抗癌、抗肥胖、抗高血糖、抗自身免疫和抗高胆固醇药物是有用的。

  公开号：

  US05157031A1
• 作为产物：
  描述：

  5-androsten-17-one 在 copper(ll) bromide 作用下， 以 甲醇 为溶剂， 反应 3.0h， 以29%的产率得到16α-bromoandrost-5-en-17-one
  参考文献：
  名称：

  Synthesis of Androst-5-en-7-ones and Androsta-3,5-dien-7-ones and Their Related 7-Deoxy Analogs as Conformational and Catalytic Probes for the Active Site of Aromatase

  摘要：

  A series of androst-5-en-7-ones and androsta-3,5-dien-7-ones and their 7-deoxy derivatives, respectively, were synthesized and tested for their abilities to inhibit aromatase in human placental microsomes. All the steroids inhibited the enzyme in a competitive manner with K-i's ranging from 0.058 to 45 mu M. The inhibitory activities of 17-oxo compounds were much more potent than those of the corresponding 17 beta-alcohols in each series. Steroids having an oxygen function (hydroxy or carbonyl) at C-19 were less potent inhibitors than the corresponding parent compounds having a 19-methyl group. 3,5-Dien-7-one 24 and its 19-hydroxy and 19-oxo derivatives (12 and 13) as well as 19-oxo-5-en-7-one 3 caused a time-dependent inactivation of aromatase only in the presence of NADPH in which the k(inact) values of 19-als 3 and 13 (0.143 and 0.189 min(-1), respectively) were larger than those of the corresponding 19-methyl (23 and 24) and 19-hydroxy (1 and 12) steroids, respectively. 19-Nor-5-en-7-one 4 but not its 3,5-diene derivative 14 also inactivated the enzyme in a time-dependent manner. In contrast, 7-deoxy steroids 21 and 27, having a 19-methyl group, did not cause it. The inactivations were prevented by the substrate androstenedione, and no significant effects of L-cysteine on the inactivations were observed in each case. The results suggest that oxygenation at C-19 would be at least in part involved in the inactivations caused by the inhibitors 23 and 24. The conjugated enone structures should play a critical role in the inactivation sequences.

  DOI：

  10.1021/jm00040a012

文献信息

• 17-Hydroxy-steroids
  申请人：——

  公开号：US04898694A1

  公开（公告）日：1990-02-06

  Compounds of the formulae: ##STR1## are useful as anti-cancer, anti-obesity, anti-diabetic, anti-coronary agents, anti-aging agents, anti-hypolipidemic agents and anti-autoimmune agents.

  式为##STR1##的化合物可用作抗癌、抗肥胖、抗糖尿病、抗冠心病、抗衰老、抗低脂血症和抗自身免疫药物。
• アンドステロン誘導体を含む慢性喘息の治療剤
  申请人：シャーロット‐メクレンバーグ・ホスピタル・ドゥーイング・ビジネス・アズ・キャロライナズ・メディカル・センター

  公开号：JP2006342180A

  公开（公告）日：2006-12-21

  【課題】 気道平滑筋の増殖を阻害し、気道平滑筋の弛緩、気管支拡張作用を有し、さらに気道上皮からの炎症性サイトカインの分泌を阻害する、動物の慢性喘息の治療剤を提供する。【解決手段】 １６α−ブロモアンドロスト−５−エン−１７−オン、１６α−ブロモ−５−アンドロスタン−１７−オン、１６α−フルオロアンドロスト−５−エン−１７−オン、１６α−フルオロ−５−アンドロスタン−１７−オン、１６β−ブロモアンドロスト−５−エン−１７−オン、１６β−ブロモ−５−アンドロスタン−１７−オン、１６β−フルオロアンドロステ−５−エン−１７−オン、１６β−フルオロ−５−アンドスタン−１７−オン等の化合物を有効成分として含有する。【選択図】 なし

  目的]提供一种用于治疗动物慢性哮喘的治疗剂，它能抑制气道平滑肌的增殖，松弛气道平滑肌，具有支气管扩张作用，还能抑制气道上皮分泌炎性细胞因子。解决方法】16α-溴雄甾烷-5-烯-17-酮、16α-溴-5Androstan-17-one, 16α-fluoro-androst-5-en-17-one, 16α-fluoro-androst-5-en-17-酮，16α-氟-5-雄甾烷-17-酮，16β-溴-雄甾烷-5-en-17-one, 16β-bromo-5-androstan-17-one, 16β-bromo-5-androstan-17-酮、16β-氟-5-雄甾烯-17-酮、16β-氟-5-雄甾烷-17-酮和 16β-氟-5-雄甾烷-17-酮。-5-雄甾烷-17-酮和其他化合物作为活性成分。无。
• Steroids useful as anti-cancer and anti-obesity agents, a therapeutic composition containing them and use thereof for the preparation of a therapeutic composition
  申请人：RESEARCH CORPORATION TECHNOLOGIES, INC.

  公开号：EP0246650B1

  公开（公告）日：1992-01-02
• Use of androsterone derivatives for inhibiting DNA binding of ap-1 and airway smooth muscle proliferation
  申请人：CHARLOTTE-MECKLENBURG HOSPITAL doing business as Carolinas Medical Center

  公开号：EP0934745B1

  公开（公告）日：2004-04-28
• System of interdependent anticancer antisense oligonucleotides targeting mRNAs the targets of which are NADPH-dependent, combined with one or more inhibitors of the Pentose Phosphate Pathway to deplete NADPH
  申请人：Nyce Jonathan Wesley

  公开号：US20170009238A1

  公开（公告）日：2017-01-12

  It is becoming increasingly clear that the genome and epigenome of another particular cancer cell represents the end product of a vast array of selection events, creating an extremely heterogeneous metabolic landscape. Since genomic and epigenomic variability exists between different cells in a tumor, the target complexity becomes even more extreme when the entire cancer cell population is considered. The only way to overcome this target complexity is by developing complex treatment modalities capable of simultaneously interdicting multiple pathways critical to the growth and survival of the cancer cell population. We have developed a method to couple suppression of NADPH levels (by inhibition of the Pentose Phosphate Pathway) with a system of antisense oligonucleotides targeting NADPH-dependent enzymes critical to the cancer cell. In the preferred embodiment of this invention, the PPP inhibitor is administered systemically, and the antisense oligonucleotides locally, directly to the tumor.