3β,17β-dihydroxy-17α-picolylandrost-5-ene

• 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,17β-dihydroxy-17α-picolylandrost-5-ene
• 英文别名: 17α-picolylandrost-5-en-3β,17β-diol；17-[2]pyridylmethyl-androst-5-ene-3β,17β-diol；17-[2]Pyridylmethyl-androst-5-en-3β,17β-diol；(3S,8R,9S,10R,13S,14S,17R)-10,13-dimethyl-17-(pyridin-2-ylmethyl)-1,2,3,4,7,8,9,11,12,14,15,16-dodecahydrocyclopenta[a]phenanthrene-3,17-diol
• 化学式: C₂₅H₃₅NO₂
• 分子量: 381.558
• InChiKey: OQIADEJTWJBWOL-SWLWOFJYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.3
• 重原子数：
  28
• 可旋转键数：
  2
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.72
• 拓扑面积：
  53.4
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  3β,17β-dihydroxy-17α-picolylandrost-5-ene 在 吡啶 、 甲醇 、 铂 作用下， 生成 3β-acetoxy-17-((Ξ)-1-acetyl-[2]piperidylmethyl)-5α-androstan-17β-ol
  参考文献：
  名称：

  17-(2-piperidylmethyl)-androstanediols

  摘要：

  公开号：

  US02853487A1
• 作为产物：
  描述：

  2-pyridylmethyllithium 、 醋酸去氢表雄酮 在 乙醚 、 苯 作用下， 生成 3β,17β-dihydroxy-17α-picolylandrost-5-ene
  参考文献：
  名称：

  关于吡啶类固醇。三，介绍一种新型吡咯啉类固醇。关于类固醇，第143部分

  摘要：

  描述了一种新型吡咯啉类固醇的合成及其氢化成去甲酚的方法。

  DOI：

  10.1002/hlca.19560390642

文献信息

• Synthesis and cytotoxic activity of some 17-picolyl and 17-picolinylidene androstane derivatives
  作者：Evgenija A. Djurendić、Jovana J. Ajduković、Marija N. Sakač、János J. Csanádi、Vesna V. Kojić、Gordana M. Bogdanović、Katarina M. Penov Gaši

  DOI：10.1016/j.ejmech.2012.06.030

  日期：2012.8

  elimination from 7 or 9 affords AB conjugated derivatives 8 and 10. Oppenauer oxidation of 1 and 2 yields 4-en-3-one derivatives 11 and 12, which, with H2O2 in 4 M NaOH, affords 4α,5α and 4β,5β-epoxides 13, 14, 16 and 17. New 4-methoxy-3-keto derivatives 15 and 18 were obtained from 13 and 14, or, with methanol in 4 M NaOH, from 16 and 17. Reduction of 11 with NaBH4 gives 22, which was then acetylated

  新的17吡啶甲基和17- picolinylidene雄甾烷衍生物，3 - 10，15，18，19，22和23，合成从17α吡啶甲基-雄甾-5-烯3β开始，17β二醇（1）和17（ Z）-吡啶甲基亚烷基-androst-5-en-3β-ol（2）。的反应1与米氯过氧酸给出5α，6α环氧N-氧化物衍生物3，或，用琼斯试剂，3,6-二酮衍生物4 ; 而17α-picolyl-androst-5-en-3β，4α，17β-triol（5）或3β，4β，17β-triol（6）衍生物可从1在二恶烷中使用SeO 2。从7或9除去碱催化的甲苯磺酰基，得到AB共轭衍生物8和10。的奥盆诺尔氧化1倍2的产率-4-烯-3-酮衍生物11和12，其中，用H 2 ö 2在4M的NaOH，得到4α，5α和4β，5β环氧化物13，14，16和17。从13和14获得了新的4-甲氧基-3-酮衍生物15和18，或在4 M
• Evaluation of A-ring fused pyridine <scp>d</scp>-modified androstane derivatives for antiproliferative and aldo–keto reductase 1C3 inhibitory activity
  作者：Marina P. Savić、Jovana J. Ajduković、Jovana J. Plavša、Sofija S. Bekić、Andjelka S. Ćelić、Olivera R. Klisurić、Dimitar S. Jakimov、Edward T. Petri、Evgenija A. Djurendić

  DOI：10.1039/c8md00077h

  日期：——

  New A-ring pyridine fused androstanes in 17a-homo-17-oxa (D-homo lactone), 17α-picolyl or 17(E)-picolinylidene series were synthesized and validated by X-ray crystallography, HRMS, IR and NMR spectroscopy. Novel compounds 3, 5, 8 and 12 were prepared by treatment of 4-en-3-one or 4-ene-3,6-dione D-modified androstane derivatives with propargylamine catalyzed by Cu(II), and evaluated for potential anticancer

  合成了 17a-homo-17-oxa ( D -homo lactone)、17α-甲基吡啶或 17( E )-甲基吡啶系列中的新型 A 环吡啶稠合雄甾烷，并通过 X 射线晶体学、HRMS、IR 和 NMR 光谱学进行了验证。新型化合物3 , 5 , 8和12通过 Cu( II )催化的炔丙基胺处理 4-en-3-one 或 4-ene-3,6-dione D-修饰的雄甾烷衍生物制备，并评估其潜在的抗癌作用体外活性使用人类癌细胞系和甾体抗癌药物的重组靶点。吡啶与 A 环的 3,4 位融合可显着增强 17α-吡啶甲基化合物对 CYP17 的亲和力，同时赋予对 PC-3 细胞的选择性抗增殖活性。类似地，吡啶与甾体D-同型内酯的 A 环融合导致发现了醛酮还原酶 1C3 的新抑制剂，这是一种针对急性髓性白血病、乳腺癌和前列腺癌的酶。一A-吡啶D-内酯类固醇5对 HT-29 结肠癌细胞还具有选择性
• Synthesis and biological evaluation of some 17-picolyl and 17-picolinylidene androst-5-ene derivatives
  作者：Katarina M. Penov Gaši、Maja Dj. Djurendić Brenesel、Evgenija A. Djurendić、Marija N. Sakač、Janoš J. Čanadi、Jovana J. Daljev、Thomas Armbruster、Silvana Andrić、Dušan M. Sladić、Tatjana T. Božić、Irena T. Novaković、Zorica D. Juranić

  DOI：10.1016/j.steroids.2006.10.002

  日期：2007.1

  Starting from dehydroepiandrosterone (1) 17-picolyl (2), 17-picolinylidene (7), 17-picolinylidene-16-one (10 and 11), and 17-picolyl-16-one (15) derivatives of androst-5-ene were synthesized in one, two, four and five steps respectively. By the Oppenauer oxidation or dehydration of 2, 7, 10, and 11 with 2,3-dichloro-5,6-dicyano-1,4-benzoquinone (DDQ), the corresponding A and B ring modified derivatives 3, 5, 6, 8, 9, and 12-14 were obtained. The structure of 2 was unambiguously proved by the appropriate X-ray structural analysis. Compounds 3, 5,9,12-14 showed inhibitory activity against the enzyme aromatase. Antibacterial activity toxicity to brine shrimp Artemia salina, antitumor activity against three tumor cell lines (human cervix carcinoma HeLa cells, human melanoma FemX cells, and human myelogenous leukemia K562 cells) and toxicity against peripheral blood mononuclear cells were evaluated. Three tested compounds, namely 11, 13, and 15, showed strong activity against all three cell lines, the IC50 values being in the range of 4-10 mu M. (c) 2006 Elsevier Inc. All rights reserved.
• Synthesis of some epoxy and/or N-oxy 17-picolyl and 17-picolinylidene-androst-5-ene derivatives and evaluation of their biological activity
  作者：Evgenija Djurendić、Jovana Daljev、Marija Sakač、Janoš Čanadi、Suzana Jovanović Šanta、Silvana Andrić、Olivera Klisurić、Vesna Kojić、Gordana Bogdanović、Maja Djurendić-Brenesel、Sladjana Novaković、Katarina Penov Gaši

  DOI：10.1016/j.steroids.2007.09.005

  日期：2008.1

  Steroidal epoxy and/or N-oxy 17-picolyl and 17-picolinylidene-androst-5-ene derivatives have been prepared using 3 beta,17 beta-dihydroxy-17 alpha-picolyl-androst-5-ene (1), 3 beta-acetoxy-17-picolinylidene-androst-5-ene (2), and 3 beta-hydroxy-17-picolinylidene-androst-5-ene (3) as synthetic precursors. The compounds 2 and/or 3 were reacted with m-chloroperoxybenzoic acid (MCPBA). The compounds synthesized from 2 were 17-picolinylidene-N-oxide 4, 5 alpha,6 alpha-epoxy and 5 beta,6 beta-epoxy-17-picolinylidene-N-oxide 5 and 6, and 5 alpha,6 alpha:17 alpha,2 alpha and 5 beta,6 beta:17 alpha,20 alpha-diepoxy-N-oxide 7 and 8. Starting from compound 3, a mixture of 5 alpha,6 alpha-epoxy and 5 beta,6 beta-epoxy-17-picolinylidene 9 and 10, 5 alpha,6 alpha-epoxy and 5 beta,6 beta-epoxy-17-picolinylidene-N-oxide 11 and 12, and 5 alpha,6 alpha:17 alpha,20 alpha- and 5 beta,6 beta:17 alpha,20 alpha-diepoxy-N-oxide 13 and 14 were obtained. From compounds 15 and 18, obtained from 1 and 3 by the Oppenauer oxidation, the 4 alpha,5 alpha-epoxy and 4 beta,5 beta-epoxy derivatives 16, 17 and 20, 21 were prepared by oxidation with 30% H2O2 Oxidation of 18 with MCPBA yielded only the N-oxide 19. The structures of compounds 15 and 18 were proved by the X-ray analysis. Compounds 1-6, 9, 15, 17, 18, and 21 were tested on activity against the enzyme aromatase. Antitumor activity against three tumor cell lines (human breast adenocarcinoma ER+, MCF-7, human breast adenocarcinoma ER-, MDA-MB-231, and prostate cancer PC3) was evaluated. Three tested compounds (1, 4, and 19) showed strong activity against PC3, the IC50 values being in the range 0.55-10 mu M, whereas compound 17 showed strong activity against MDA-MB-231 (IC50 10.4 mu M). (C) 2007 Elsevier Inc. All rights reserved.
• Über Pyridyl-Steroide. III. Darstellung eines neuartigen Pyrrocolin-Steroids. Über Steroide, 143. Mitteilung
  作者：J. Heer、K. Hoffmann

  DOI：10.1002/hlca.19560390642

  日期：——

  Es wird die Synthese eines neuartigen Pyrrocolin- Steroids und dessen Hydrierung zu einem Nor-solaniden beschrieben.

  描述了一种新型吡咯啉类固醇的合成及其氢化成去甲酚的方法。