20-aLpha-二氢可的松 | 1719-79-5

• 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: 20-aLpha-二氢可的松
• 英文名称: 11β,17α,20β,21-tetrahydroxypregn-4-en-3-one
• 英文别名: 4-pregnen-11β,17α,20β,21-tetrol-3-one；11β,17,20α,21-tetrahydroxy-4-pregnen-3-one；20α-dihydrocortisol；dihydrocortisol；11β,17,20α_F,21-tetrahydroxy-pregn-4-en-3-one；11β,17,20α_F,21-Tetrahydroxy-pregn-4-en-3-on；20alpha-Dihydrocortisol；(8S,9S,10R,11S,13S,14S,17R)-17-[(1S)-1,2-dihydroxyethyl]-11,17-dihydroxy-10,13-dimethyl-2,6,7,8,9,11,12,14,15,16-decahydro-1H-cyclopenta[a]phenanthren-3-one
• CAS: 1719-79-5
• 化学式: C₂₁H₃₂O₅
• 分子量: 364.482
• InChiKey: AWWCEQOCFFQUKS-FJWDNACWSA-N

物化性质

• 熔点：
  250-252 °C
• 沸点：
  586.6±50.0 °C(Predicted)
• 密度：
  1.29±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.8
• 重原子数：
  26
• 可旋转键数：
  2
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.86
• 拓扑面积：
  98
• 氢给体数：
  4
• 氢受体数：
  5

上下游信息

• 上游原料

  中文名称	英文名称	CAS号	化学式	分子量
  氢化可的松	HYDROCORTISONE	50-23-7	C21H30O5	362.466

反应信息

• 作为反应物：
  描述：

  20-aLpha-二氢可的松 、 乙酸酐 在 吡啶 作用下， 生成 20α_F,21-diacetoxy-11β,17-dihydroxy-pregn-4-en-3-one
  参考文献：
  名称：

  从人的尿液中分离出delta 4-pregnene-11 beta，17 alpha，20 alpha，21-tetrol-3-one。

  摘要：

  DOI：

  10.1016/0003-9861(57)90149-2
• 作为产物：
  描述：

  D-葡萄糖-2-13C 生成 20-aLpha-二氢可的松
  参考文献：
  名称：

  Hogg et al., Journal of the American Chemical Society, 1955, vol. 77, p. 4436

  摘要：

  DOI：

文献信息

• Asymmetric reduction of steroidal 20-ketones: Chemical synthesis of corticosteroid derivatives containing and 20α, 21-diol and 17α, 20α, 21-triol side chains
  作者：C Arthur Han

  DOI：10.1016/0039-128x(83)90125-3

  日期：1983.12

  Abstract A method is presented for the chemical synthesis of corticosteroid derivatives containing the 20α, 21-diol and 17α, 20α, 21-triol side chains. The ketol side chains of cortisol, corticosterone, 11-deoxycortisol, and 11-deoxycorticosterone were reduced at C-20 with sodium borohydride in a two-phase system consisting of aqueous calcium chloride and an organic phase of chloroform or ethyl acetate

  摘要 提出了一种化学合成含有 20α, 21-二醇和 17α, 20α, 21-三醇侧链的皮质类固醇衍生物的方法。在由氯化钙水溶液和氯仿或乙酸乙酯的有机相组成的两相系统中，皮质醇、皮质酮、11-脱氧皮质醇和 11-脱氧皮质酮的酮醇侧链在 C-20 处用硼氢化钠还原。还原的立体选择性是 92% α 取向的皮质醇和 79% α 取向的 11-脱氧皮质醇在 -27°。随着温度的升高，20α-形式相对于20β-形式减少。对于 17-脱氧类固醇，11-脱氧皮质酮还原为 20α 形式的比例为 23%，皮质酮为 41%。17-脱氧类固醇的 20α 20β 比率在 0° 和 -27° 之间没有变化。钙离子增加了皮质类固醇在水相中的溶解度。我们建议钙离子通过与 17α-羟基类固醇的侧链形成双齿复合物，将它们固定在有利于 20α-还原的方向，并通过改变类固醇的相分配来影响还原的立体化学。
• C-20 ketone reduction of hydrocortisone by rice field microalga Chlorella vulgaris MCCS 013
  作者：Younes Ghasemi、Sara Rasoul-Amini、Mohammad Hossein Morowvat、Mohammad Bagher Ghoshoon、Mohammad Javad Raee、Soraya Khoubani、Narges Negintaji、Fatemeh Nouri、Rezvan Parvizi

  DOI：10.1007/s10600-010-9496-6

  日期：2009.11

  A unicellular microalga, Chlorella vulgaris, was isolated from rice field and applied in the biotransformation experiment of hydrocortisone (1). This strain has not been previously tested for hydrocortisone bioconversion. Fermentation was carried out in BG-11 medium supplemented with 0.05% substrate at 25°C for 14 days incubation. The products obtained were chromatographically purified followed by their characterization using spectroscopic methods. 11β,17α,20β,21-Tetrahydroxypregn-4-en-3-one (2), 11β,17β-dihydroxyandrost-4-en-3-one (3), and 11β-hydroxyandrost-4-ene-3,17-dione (4) were the main bioproducts in the hydrocortisone bioconversion. Bioreaction characteristics observed were 20-ketone reduction for accumulation of compound 2 and side chain degradation of the substrate to prepare compounds 3 and 4. Time course study showed the accumulation of the product 2 from the second day of the fermentation and 3 as well as 4 from the third day. All the metabolites reached their maximum concentration in seven days. Microalgal 18S rRNA gene was also amplified by PCR. PCR products were sequenced to confirm their authenticity as 18S rRNA gene of microalgae. The result of PCR blasted with other sequenced microalgae in NCBI showed 100% homology to the 18S small subunit rRNA of six strains of Chlorella vulgaris.

  从稻田中分离出一种单细胞微藻--普通小球藻，并将其应用于氢化可的松的生物转化实验（1）。该菌株以前从未进行过氢化可的松生物转化试验。发酵在添加了 0.05% 底物的 BG-11 培养基中进行，培养温度为 25°C，培养时间为 14 天。获得的产物经色谱纯化，然后用光谱方法进行表征。11β,17α,20β,21-四羟基孕甾-4-烯-3-酮（2）、11β,17β-二羟基雄甾-4-烯-3-酮（3）和 11β-羟基雄甾-4-烯-3,17-二酮（4）是氢化可的松生物转化过程中的主要生物产物。观察到的生物反应特征是 20 酮还原生成化合物 2，底物侧链降解生成化合物 3 和 4。时间进程研究表明，产物 2 从发酵的第二天开始积累，3 和 4 从发酵的第三天开始积累。所有代谢物都在七天内达到最大浓度。还通过 PCR 扩增了微藻 18S rRNA 基因。对 PCR 产物进行了测序，以确认其为微藻的 18S rRNA 基因。PCR 与 NCBI 中其他微藻的测序结果显示，与六株小球藻的 18S 小亚基 rRNA 有 100% 的同源性。
• HETERODIMER COMPOSITIONS AND METHODS FOR THE TREATMENT OF OCULAR DISORDERS
  申请人：Ripple Therapeutics Corporation

  公开号：US20210347809A1

  公开（公告）日：2021-11-11

  Described herein are processable compositions comprising at least one moiety that is processable in its free form. Also described herein are compositions and methods for the treatment of ocular diseases or disorders including glaucoma, blepharitis, ocular inflammation, diabetic macular edema, posterior inflammation, anterior inflammation, macular degeneration (e.g., wet macular degeneration (AMD) or dry AMD), post-cataract surgery, and retinal vein occlusion. Said compositions and methods comprise steroids and prostaglandins which demonstrate anti-inflammatory activity, intraocular pressure (IOP) lowering, and/or other desirable activities. Injection of said compositions in the eye provides therapeutic benefit to patients suffering from ocular disorders.

  本文描述了可加工的组合物，其中至少包含一个可在其自由形式下加工的成分。本文还描述了用于治疗眼部疾病或障碍的组合物和方法，包括青光眼、眼睑炎、眼部炎症、糖尿病性黄斑水肿、后部炎症、前部炎症、黄斑变性（如湿性黄斑变性（AMD）或干性AMD）、白内障手术后和视网膜静脉阻塞。所述组合物和方法包括表现出抗炎活性、降低眼内压力（IOP）和/或其他理想活性的类固醇和前列腺素。将所述组合物注射到眼中可为患有眼部障碍的患者提供治疗益处。
• Neuroactive steroid formulations and methods of treating CNS disorders
  申请人：Sage Therapeutics, Inc.

  公开号：US10322139B2

  公开（公告）日：2019-06-18

  Formulations of comprising a neuroactive steroid, e.g., allopregnanolone; and optionally a cyclodextrin, e.g., a β-cyclodextrin, e.g., a sulfo butyl ether β-cyclodextrin, e.g., a β-cyclodextrin, e.g., a sulfo butyl ether β-cyclodextrin, e.g., CAPTISOL®; and methods of use in treating CNS disorders.

  该配方包括一种神经活性类固醇，例如，孕酮醇；以及可选的环糊精，例如β-环糊精，例如磺酸丁基醚β-环糊精，例如β-环糊精，例如磺酸丁基醚β-环糊精，例如CAPTISOL®；以及在治疗中枢神经系统疾病方面的使用方法。
• Inhibition of migration inhibitory factor in the treatment of diseases involving cytokine mediated toxicity
  申请人：THE PICOWER INSTITUTE FOR MEDICAL RESEARCH

  公开号：EP1741779A2

  公开（公告）日：2007-01-10

  The present invention relates to compositions and methods for inhibiting the release and/or biological activity of migration inhibitory factor (MIF). In particular, the invention relates to the uses of such compositions and methods for the treatment of various conditions involving cytokine-mediated toxicity, which include, but are not limited to shock, inflammation, graft versus host disease, and/or autoimmune diseases.

  本发明涉及抑制迁移抑制因子（MIF）释放和/或其生物活性的组合物和方法。 特别是，本发明涉及将此类组合物和方法用于治疗涉及细胞因子介导的毒性的各种病症，其中包括但不限于休克、炎症、移植物抗宿主疾病和/或自身免疫性疾病。