Δ¹-11-deoxycorticosterone | 5508-55-4

• 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
• 英文名称: Δ¹-11-deoxycorticosterone
• 英文别名: (+)-21-hydroxy-3,20-dioxo-pregna-1,4-diene；21-hydroxypregna-1,4-diene-3,20-dione；21-hydroxy-pregna-1,4-diene-3,20-dione；21-Hydroxy-pregna-1,4-dien-3,20-dion；21-hydroxy-1,4-pregnadiene-3,20-dione；1-Dehydro-desoxycorticosteron；1,4-Pregnadien-21-ol-3,20-dione；(8S,9S,10R,13S,14S,17S)-17-(2-hydroxyacetyl)-10,13-dimethyl-6,7,8,9,11,12,14,15,16,17-decahydrocyclopenta[a]phenanthren-3-one
• CAS: 5508-55-4
• 化学式: C₂₁H₂₈O₃
• 分子量: 328.452
• InChiKey: ZDYFFPNLCUDFDB-YFWFAHHUSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  24
• 可旋转键数：
  2
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.71
• 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：

  Δ¹-11-deoxycorticosterone 在 sodium periodate 作用下， 以 1,4-二氧六环 、 水 为溶剂， 生成 (+)-3-oxoandrosta-1,4-diene-17β-carboxylic acid
  参考文献：
  名称：

  (+)-3-Oxoandrosta-1,4-diene-17β-carboxylic acid: catemeric hydrogen bonding in a steroidal keto acid

  摘要：

  The title keto acid, C20H26O3, forms translational carboxyl-ketone hydrogen-bonding catemers [O ... O = 2.665(3)Angstrom]. The cell contains two molecules screw-related in b, with opposite end-to-end orientation, yielding two parallel, counterdirectional screw-related hydrogen-bonding chains. Intermolecular C-H ... O = C close contacts to the carboxyl group were found, involving three different neighboring molecules.

  DOI：

  10.1107/s0108270199007519
• 作为产物：
  描述：

  progesterone 在 lead(IV) acetate 、 potassium hydrogencarbonate 、 溶剂黄146 作用下， 生成 Δ¹-11-deoxycorticosterone
  参考文献：
  名称：

  The Reaction of Lead Tetraacetate with Progesterone and Testosterone

  摘要：

  DOI：

  10.1021/ja01608a036

文献信息

• Mikrobiologische Herstellung von 1-Dehydro-Steroiden. Mikrobiologische Reaktionen, 6. Mitteilung
  作者：E. Vischer、Ch. Meystre、A. Wettstein

  DOI：10.1002/hlca.19550380328

  日期：——

  It has been shown that the compounds, the formation of which by incubation of cortisone and 17α-hydroxy-cortexone with molds of the genus Fusarium was mentioned in an earlier paper, are the corresponding 1-dehydro compounds.

  已经表明，在较早的论文中提到了通过将可的松和17α-羟基-皮质酮与镰孢属的霉菌一起孵育而形成的化合物，是相应的1-脱氢化合物。
• CYP260B1 acts as 9α-hydroxylase for 11-deoxycorticosterone
  作者：Martin Litzenburger、Rita Bernhardt

  DOI：10.1016/j.steroids.2017.08.006

  日期：2017.11

  cytochromes P450 play an important role for the functionalization of steroidal compounds. In this study, we elucidated the main product of 11‐deoxycorticosterone conversion formed by CYP260B1 from Sorangium cellulosum So ce56 as 9&agr;‐OH 11‐deoxycorticosterone by NMR spectroscopy. This is, to the best of our knowledge, the first identification of a 9&agr;‐hydroxylase for this substrate. In addition, the major

  亮点CYP260B1 充当11-脱氧皮质酮的9&agr;-羟化酶。CYP260B1 的T224A 突变体增加了选择性。可实现约0.25 g/l/d 的生产率。摘要 类固醇及其氧官能化对应物是制药行业的重要化合物。然而，氧的区域和立体选择性引入对于合成化学来说是一项具有挑战性的任务。因此，细胞色素 P450 在甾体化合物的功能化中起着重要作用。在这项研究中，我们通过 NMR 光谱阐明了 11-脱氧皮质酮转化的主要产物是 9&agr;-OH 11-脱氧皮质酮。据我们所知，这是首次鉴定出该底物的 9α-羟化酶。此外，主要副产物被鉴定为 21-OH pregna-1,4-diene-3,20-dione。使用 1&agr;-OH 11-脱氧皮质酮作为底物的研究表明，主要副产物是通过脱氢反应形成的。通过使用 CYP260B1-T224A 突变体，这种副反应显着减少，与野生型的 60% 相比，9α-羟基化选择性增加了约
• COMBINATION THERAPY OF ARTHRITIS WITH TRANILAST
  申请人：PEARLMAN Rodney

  公开号：US20100158905A1

  公开（公告）日：2010-06-24

  Combination therapy is disclosed herein for the treatment an arthritic condition (e.g. rheumatoid arthritis, osteoarthritis or psoriatic arthritis). The therapies disclosed herein comprise administering tranilast or an analogous compound in combination with a pharmaceutical agent, such as a non-steroidal anti-inflammatory drug, a disease-modifying drug, a COX-2 inhibitor, an antibiotic, an analgesic or combination thereof.

  本文披露了一种治疗关节炎症状（例如类风湿性关节炎、骨关节炎或银屑病性关节炎）的联合治疗方案。本文所披露的治疗方案包括与药物剂量联合使用曲安那或类似化合物，例如非甾体抗炎药、疾病修饰药、COX-2抑制剂、抗生素、镇痛药或以上药物的联合使用。
• 4-Halo-pregn-4-enes, their preparation and pharmaceutical use
  申请人：SYNTEX (U.S.A.) INC.

  公开号：EP0004766A2

  公开（公告）日：1979-10-17

  4-Halo-pregn-4-enee of the formula: wherein X' is fluoro or chloro; X2 is hydrogen, fluoro or chloro; X3 is hydrogen, fluoro, chloro or bromo; X4 is =C=O or or may be when X3 is chloro; R' is hydrogen, fluoro, chloro, bromo, hydroxy or methoxy; R2 is fluoro, chloro, hydroxy or alkanoyloxy of 2 to 6 carbon atoms when R' is hydrogen or R2 is the same as R1 when R' is fluoro, chloro, hydroxy or methoxy; R3 is hydroxy or alkanoyloxy of 2 to 6 carbon atoms when R4 is a-methyl or β-methyl or R3 and R4 together are and the solid and broken lines between the 1- and 2-positions in the A ring of the steroid nucleus represents a single or a double bond; have topical anti-inflammatory activity in mammals. They can be prepared by contacting the corresponding A5 compound with a base. The 17a-alkanoyloxy compound can be prepared by esterifying the corresponding 17a-hydroxy compound.

  式中的 4-卤代-4-孕烯： 其中 X'是氟或氯 X2 是氢、氟或氯 X3 是氢、氟、氯或溴； X4 是 =C=O 或 或可以是 当 X3 为氯时； R' 是氢、氟、氯、溴、羟基或甲氧基； R2 是氟代、氯代、羟基或 2 至 6 个碳原子的烷酰氧基。 当 R' 为氢或 R2 与 R1 相同时，R2 为氟、氯、羟基或 2 至 6 个碳原子的烷酰氧基 当 R' 为氟、氯、羟基或甲氧基时； 当 R4 为 a-甲基或 β-甲基时，R3 为羟基或 2 至 6 个碳原子的烷酰氧基，或 R3 和 R4 合在一起为 和 类固醇核 A 环上 1 位和 2 位之间的实线和断线代表单键或双键；对哺乳动物具有局部抗炎活性。它们可以通过将相应的 A5 化合物与碱接触来制备。17a-alkanoyloxy 化合物可通过酯化相应的 17a-hydroxy 化合物制备。
• 16,17-Acetal-substituted androstane-17-beta-carboxylic-acid esters, process for their preparation and pharmaceutical compound containing them
  申请人：Aktiebolaget Draco

  公开号：EP0197018A1

  公开（公告）日：1986-10-08

  The invention refers to compounds having anti- inflammetory activity characterized by the formula or a stereoisomeric component thereof, in which formula the 1,2-position is saturated or is a double band X, is selected from hydrogen, fluorine, chlorine and bromine X2 is selected from hydrogen, fluorine, chlorine and bromine R1 is selected from hydrogen or a straight or branched hydrocarbon chain having 1-4 carbon atoms R2 is selected from hydrogen or straight and branched hydrocarbon chains having 1-10 carbon atoms and R3 is selected from Y is O or S R4 is selected from hydrogen, straight or branched hydrocarbon chains having 1-10 carbon atoms or from phenyl R5 is selected from hydrogen or methyl and R6 is selected from hydrogen, straight or branched, saturated or unsaturated hydrocarbon chains having 1-10 carbon atoms, an alkyl group substituted by at least one halogen atom, a heterocyclic ring system containing 3-10 atoms in the ring system, -(CH2)m CH(CH2)n (m=0,1,2; n=2,3,4,5,6), phenyl or benzyl groups which are unsubstituted or substituted by one or more alkyl, nitro, carboxy, alkoxy, halogen, cyano, carbalkoxy or trifluoromethyl group(s), provided that when R2 is hydrogen R1 is methyl. The invention also refers to a process and intermediates for the preparation of these compounds, a pharmaceutical preparation containing one of the compounds and a method for the treatment of inflammatory conditions.

  本发明涉及具有抗炎活性的化合物，其特征为式 或其立体异构体成分，其中式中 1,2 位饱和或为双带 X，选自氢、氟、氯和溴 X2 选自氢、氟、氯和溴 R1 选自氢或具有 1-4 个碳原子的直链或支链烃链 R2 选自氢或具有 1-10 个碳原子的直链或支链烃链，以及 R3 选自 Y 是 O 或 S R4 选自氢、具有 1-10 个碳原子的直链或支链烃链或苯基 R5 选自氢或甲基 R6 选自氢、具有 1-10 个碳原子的直链或支链饱和或不饱和烃链、被至少一个卤素原子取代的烷基、环系中含有 3-10 个原子的杂环、-(CH2)m CH(CH2)n （m=0,1,2；n=2,3,4,5,6）、未被取代或被一个或多个烷基、硝基、羧基、烷氧基、卤素、氰基、碳烷氧基或三氟甲基取代的苯基或苄基，条件是当 R2 为氢时，R1 为甲基。 本发明还涉及制备这些化合物的工艺和中间体、含有其中一种化合物的药物制剂以及治疗炎症的方法。