19-羟孕酮 | 596-63-4

• 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: 19-羟孕酮
• 中文别名: 19-羟基黄体激素
• 英文名称: 19-Hydroxyprogesterone
• 英文别名: 19-Hydroxy-progesteron；(8S,9S,10S,13S,14S,17S)-17-acetyl-10-(hydroxymethyl)-13-methyl-1,2,6,7,8,9,11,12,14,15,16,17-dodecahydrocyclopenta[a]phenanthren-3-one
• CAS: 596-63-4
• 化学式: C₂₁H₃₀O₃
• 分子量: 330.467
• InChiKey: FIHWBGCIKMXLBI-NXMWLWCLSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  24
• 可旋转键数：
  2
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.809
• 拓扑面积：
  54.4
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  19-羟孕酮 在 吡啶 作用下， 以 丙酮 为溶剂， 反应 21.0h， 生成 Thioacetic acid S-((8S,9S,10S,13S,14S,17S)-17-acetyl-13-methyl-3-oxo-1,2,3,6,7,8,9,11,12,13,14,15,16,17-tetradecahydro-cyclopenta[a]phenanthren-10-ylmethyl) ester
  参考文献：
  名称：

  6,19-Sulfur-Bridged Progesterone Analogues with Antiimmunosuppressive Activity

  摘要：

  Sulfur-bridged pregnanes 6,19-epithioprogesterone, 21-hydroxy-6,19-epithioprogesterone, and the corresponding sulfoxides and sulfones were synthesized and tested as blockers of the immunosuppresive activity of dexamethasone in rat thymocytes. A new one-pot procedure is described for the preparation of 6,19-epithioprogesterone and related compounds by iodocyclization of a 19-sulfanylpregn-5-ene. Antiimmunosuppresive activity was evaluated by the ability of the different steroids to block dexamethasone-inediated apoptosis in thymocytes and dexamethasone-mediated inhibition of the NF kappa-B transcription factor activity. DNA fragmentation and annexin V-FITC positive cells were taken as parameters of apoptosis whereas NF kappa-B activity was tested by the expression of the reporter vector kappa B-luciferase by TNF-alpha in Hela cells. 21-Hydroxy-6,19-epithioprogesterone S,S-dioxide-had improved activity in both parameters, while 21-hydroxy-6,19-epithioprogesterone had improved activity only in blocking dexamethasone-induced programmed cell death.

  DOI：

  10.1021/jm049266x
• 作为产物：
  描述：

  孕烯醇酮醋酸酯 在 甲醇 、 N-溴代丁二酰亚胺(NBS) 、 高氯酸 、 碘 、 lead(IV) tetraacetate 、 碳酸氢钠 、 potassium carbonate 、 戴斯-马丁氧化剂 、 溶剂黄146 、 锌 作用下， 以 1,4-二氧六环 、 二氯甲烷 、 环己烷 、 水 、 异丙醇 为溶剂， 反应 18.67h， 生成 19-羟孕酮
  参考文献：
  名称：

  19-羟基孕酮的合成及6,19-环氧桥开环机制的深入研究

  摘要：

  摘要 通过七个步骤获得了高效且可规模化的19-羟基孕酮合成工艺，总收率34.5%，远高于文献报道的工艺（总收率11.0%）。首次提出了化合物7中 6,19-环氧桥的合理开环机理，并且反应混合物的 LC-MS 分析支持了中间体的结构。

  DOI：

  10.1080/10286020.2022.2144260

文献信息

• Synthesis of 6,19-cyclopregnanes. Constrained analogues of steroid hormones
  作者：Pablo H. Di Chenna、Adriana S. Veleiro、Juan M. Sonego、Nora R. Ceballos、M. Teresa Garland、Ricardo F. Baggio、Gerardo Burton

  DOI：10.1039/b706828j

  日期：——

  A procedure for the synthesis of 6,19-cyclopregnanes is described involving an intramolecular alkylation reaction of Delta(4)-3-keto steroids with a 19-mesylate in the presence of KOH in isopropanol. Three 6,19-cyclopregnanes were prepared (4, 5 ,9); in the rat, 6,19-cycloprogesterone (4) and its 21-hydroxy derivative 5 displaced [3H]-dexamethasone from glucocorticoid receptors, the former compound

  描述了合成6,19-环孕烷的方法，该方法涉及在异丙醇中存在KOH的情况下，Delta（4）-3-酮类固醇与19-甲磺酸酯的分子内烷基化反应。制备了三个6,19-环孕烷（4，5，9）; 在大鼠中，6,19-环孕酮（4）及其21-羟基衍生物5从糖皮质激素受体中置换了[3H]-地塞米松，前一种化合物的活性更高。两种化合物均未与[3H]-醛固酮竞争肾上腺皮质激素受体竞争，也未与[3H] -R5020竞争子宫孕激素受体竞争。
• Preparation and Properties of Three Immunogens with a Spacer on the β-Side of the Steroid Skeleton and the Effect of Immunogen Structure on Specificity of the Obtained Antisera
  作者：Alexander Kasal、Richard Hampl、Zdeněk Putz、Ladislav Kohout、Luboslav Stárka

  DOI：10.1135/cccc19922166

  日期：——

  Three haptenes for the determination of Reichstein's compound S and progesterone were prepared in which hemisuccinyloxy group was attached to the β-side of the steroid skeleton (compounds VII, XIII and XV). These haptenes were bound to BSA and used for preparation of antisera. The specificity of these antisera was compared with that of antisera obtained with usual immunogens.

  为了测定Reichstein的化合物S和孕酮，制备了三种半抗原，其中半琥珀酰氧基团附着在类固醇骨架的β侧（化合物VII、XIII和XV）。这些半抗原被结合到BSA上，并用于制备抗血清。将这些抗血清的特异性与通常免疫原获得的抗血清进行了比较。
• 19-Nor and aromatic steroids. Part II. Cleavage of 3-oxygenated 4β,19-ethers in the pregnane series leading to 19-norprogesterone
  作者：Ruth E. Gall (Née Lack)、Jacques E. Nemorin、Leonard Tarasoff

  DOI：10.1039/p19740000881

  日期：——

  Treatment of pregn-4-ene-3β,20β-diol with m-chloroperbenzoic acid gave the 4β,5β-epoxide (IIa), which was separated from the 4α,5α-isomer by recrystallisation. Acetylation of the β-epoxide (IIa) followed by hydrogenation over platinum oxide in acetic acid gave 3β,20β-diacetoxy-5α-pregnan-4β-ol, readily converted into the 4β,19-epoxide (XIIa) by reaction with lead tetra-acetate. Oxidation then gave

  孕甾-4-烯-3β处理，20β二醇与米氯过苯甲酸，得到4β，5β-环氧化物（II a）中，将其从4α，5α异构体通过重结晶分离。β型环氧化物（乙酰化II随后氢化过乙酸氧化铂），得到3β，20β二乙酰氧基5α孕4β醇，容易地转化成4β，19-环氧化物（XII由反应a）用四乙酸铅。然后氧化，得到环氧二酮（XIII），将其用三氟化硼在乙酸酐中裂解，主要得到4α，19-二乙酰氧基戊烯-3，20-二酮。在甲醇中小心水解10分钟，得到4α，19-二醇（XIVb）; 可以将其转化为19-羟基孕酮（Ic），也可以将其转化为19-正孕酮。
• Sulphur analogues of 21-hydroxy-6,19-oxidoprogesterone (21oh-6op) for treating excess of glucocorticoids
  申请人：——

  公开号：US20040029846A1

  公开（公告）日：2004-02-12

  The present invention is related to novel 21-hydroxy-6,19-oxidoprogesterone (21OH-6OP) analogues, their use as antiglucocorticoids for the treatment and/or prophylaxis of diseases associated to an excess of glucocorticoids. In particular, the invention relates to the use of novel 21-hydroxy-6,19-oxidoprogesterone (21OH-6OP) analogues having the formula FORMULAwherein X is S, SO and SO2, and R is either M or OH, for treating Cushing's syndrome, iatrogenic hypercortisolism or depression. Also the present invention is related to methods of preparing the novel 21-hydroxy-6,19-oxidoprogesterone (21OH-6OP) analogues. 1

  本发明涉及新型21-羟基-6,19-氧代孕酮（21OH-6OP）类似物，其用作抗糖皮质激素治疗和/或预防与糖皮质激素过量相关的疾病。具体来说，本发明涉及使用具有以下公式的新型21-羟基-6,19-氧代孕酮（21OH-6OP）类似物，其中X为S、SO和SO2，R为M或OH，用于治疗库欣综合征、医源性高皮质醇血症或抑郁症。此外，本发明还涉及制备新型21-羟基-6,19-氧代孕酮（21OH-6OP）类似物的方法。
• 19-substituted progesterone derivatives useful as 19-hydroxylase
  申请人：Merrell Dow Pharmaceuticals Inc.

  公开号：US04910191A1

  公开（公告）日：1990-03-20

  19-Substituted progesterone derivatives and related compounds which are active as 19-hydroxylase inhibitors and useful as antihypertensive agents are described herein. The compounds are prepared using appropriate synthetic pathways which will vary according to the nature of the specific 19-substituted progesterone or related compound desired.

  本文描述了作为19-羟化酶抑制剂活性并且作为降压药物有用的19-取代孕酮衍生物及相关化合物。这些化合物是使用适当的合成途径制备的，这些途径将根据所需的特定19-取代孕酮或相关化合物的性质而有所不同。