四氢可的松 | 53-05-4

• 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: 四氢可的松
• 英文名称: tetrahydrocortisone
• 英文别名: 3α,17,21-trihydroxy-5β-pregnane-11,20-dione；(3R,5R,8S,9S,10S,13S,14S,17R)-3,17-dihydroxy-17-(2-hydroxyacetyl)-10,13-dimethyl-2,3,4,5,6,7,8,9,12,14,15,16-dodecahydro-1H-cyclopenta[a]phenanthren-11-one
• CAS: 53-05-4
• 化学式: C₂₁H₃₂O₅
• 分子量: 364.482
• InChiKey: SYGWGHVTLUBCEM-ZIZPXRJBSA-N

物化性质

• 熔点：
  190°
• 比旋光度：
  D25 +85.5° (abs ethanol)
• 沸点：
  415.66°C (rough estimate)
• 密度：
  1.0666 (rough estimate)
• 溶解度：
  乙醇（微溶）、甲醇（微溶）

计算性质

• 辛醇/水分配系数(LogP)：
  2.2
• 重原子数：
  26
• 可旋转键数：
  2
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.9
• 拓扑面积：
  94.8
• 氢给体数：
  3
• 氢受体数：
  5

安全信息

• 储存条件：
  本品应密封存放在阴凉、干燥、避光的地方保存。

制备方法与用途

生物活性方面， Tetrahydrocortisone 是一种应激性激素，它是由 5-还原酶将 Cortisone 还原而成的 Cortisone 的尿液代谢产物。

反应信息

• 作为反应物：
  描述：

  四氢可的松 在 N-溴代乙酰胺 作用下， 生成 5-beta-二氢化可的松
  参考文献：
  名称：

  Partial Synthesis of Compounds Related to Adrenal Cortical Hormones. XVI. Preparation of Cortisone and Related Compounds¹

  摘要：

  DOI：

  10.1021/ja01122a060
• 作为产物：
  描述：

  可的松 生成 四氢可的松
  参考文献：
  名称：

  真菌Alternaria bataticola对Delta 4-3-酮孕烯化合物的微生物还原作用。

  摘要：

  DOI：

  10.1016/0003-9861(59)90473-4
• 作为试剂：
  描述：

  5-氰基邻苯二甲酰亚胺 在 i-PrEtN 、 四氢可的松 、 一水合肼 、 三乙胺 、 三氯氧磷 作用下， 以 乙醇 为溶剂， 反应 15.0h， 生成 4-chloro-1-(3-chloro-4-ethoxybenzyl)amino-6-cyano-phthalazine
  参考文献：
  名称：

  4-Benzylamino-1-chloro-6-substituted Phthalazines:  Synthesis and Inhibitory Activity toward Phosphodiesterase 5

  摘要：

  We synthesized various 4-benzylamino-1-chloro-6-substituted phthalazines (15) and 4-benzylamino-1-chloro-7-substituted phthalazines (16) and evaluated their inhibitory activity toward phosphodiesterase 5 (PDE5) purified from porcine platelets. The PDE5-inhibitory activities of 15 were greater than those of the isomers (16). The preferred substituent at the 4-position of phthalazine was a (3-chloro-4-methoxybenzyl)amino group, and those at the B-position were cyano, nitro, and trifluoromethyl groups. Compounds 15a (IC50 = 4.8 nM), 15f (3.5 nM), and 15i (5.3 nM) were more potent inhibitors than E4021 (8.6 nM). Compounds 15a and 15f also showed vasorelaxant activity in isolated porcine coronary arteries precontracted with prostaglandin F-2 alpha (10(-5) M). The EC50 values for vasorelaxant action of 15a, 15f, and E4021 were 150, 160, and 980 nM, respectively. These results show that novel PDE5 inhibitors possessing a potent vasorelaxant effect may exist among phthalazine derivatives.

  DOI：

  10.1021/jm970815r

文献信息

• NEW STEROIDS HAVING INCREASED WATER SOLUBILITY AND RESISTANCE AGAINST METABOLISM, AND METHODS FOR THEIR PRODUCTION
  申请人：BACKSTROM Torbjorn

  公开号：US20080119416A1

  公开（公告）日：2008-05-22

  Steroid compounds having increased resistance against metabolism and increased water solubility are disclosed, together with methods for their production. These substances are suitable for the manufacture of pharmaceuticals for the treatment of steroid related or steroid induced CNS disorders and for use in methods of prevention, alleviation or treatment of such disorders.

  揭示了具有增加代谢抵抗力和增加水溶性的类固醇化合物，以及它们的生产方法。这些物质适用于制造用于治疗与类固醇相关或类固醇诱导的中枢神经系统疾病的药物，并用于预防、缓解或治疗此类疾病的方法。
• Modulators of 11- beta hydroxyl steroid dehydrogenase type 1, pharmaceutical compositions thereof, and methods of using the same
  申请人：Zhuo Jincong

  公开号：US20070208001A1

  公开（公告）日：2007-09-06

  The present invention relates to inhibitors of 11-β hydroxyl steroid dehydrogenase type 1 and pharmaceutical compositions thereof. The compounds of the invention can be useful in the treatment of various diseases associated with expression or activity of 11-β hydroxyl steroid dehydrogenase type 1.

  本发明涉及11-β羟基类固醇脱氢酶1型的抑制剂及其药物组合物。本发明的化合物可用于治疗与11-β羟基类固醇脱氢酶1型的表达或活性相关的各种疾病。
• 2-Methylprop anamides and their use as pharmaceuticals
  申请人：Yao Wenqing

  公开号：US20050288329A1

  公开（公告）日：2005-12-29

  The present invention relates to inhibitors of 11-β hydroxyl steroid dehydrogenase type 1, antagonists of the mineralocorticoid receptor (MR), and pharmaceutical compositions thereof. The compounds of the invention can be useful in the treatment of various diseases associated with expression or activity of 11-β hydroxyl steroid dehydrogenase type 1 and/or diseases associated with aldosterone excess.

  本发明涉及11-β羟基类固醇脱氢酶1型的抑制剂、矿物皮质激素受体（MR）的拮抗剂以及其药物组合物。本发明的化合物可用于治疗与11-β羟基类固醇脱氢酶1型的表达或活性以及与醛固酮过量相关的各种疾病。
• Modulators of 11-beta hydroxyl steroid dehydrogenase type 1, pharmaceutical compositions thereof, and methods of using the same
  申请人：Yao Wenqing

  公开号：US20070197506A1

  公开（公告）日：2007-08-23

  The present invention relates to inhibitors of 11-β hydroxyl steroid dehydrogenase type 1 and pharmaceutical compositions thereof. The compounds of the invention can be useful in the treatment of various diseases associated with expression or activity of 11-β hydroxyl steroid dehydrogenase type 1 such as obesity and diabetes.

  本发明涉及11-β羟基类固醇脱氢酶1型的抑制剂及其药物组合物。本发明的化合物可用于治疗与11-β羟基类固醇脱氢酶1型的表达或活性相关的各种疾病，如肥胖和糖尿病。
• Arylpyrrole insecticidal acaricidal and nematicidal agents and methods
  申请人：American Cyanamid Company

  公开号：US05010098A1

  公开（公告）日：1991-04-23

  This invention is directed to certain novel insecticidal, acaricidal and nematicidal arylpyrrole agents and a method for controlling insects, acarids and nematodes therewith. The invention also is directed to a method for protecting growing plants from insect, acarid and nematode attack by applying to said plants or the soil in which they are growing, an insecticidally, acaricidally or nematicidally effective amount of a novel arylpyrrole compound. The present invention further is directed to a method for the preparation of the arylpyrrole compounds.

  该发明涉及一种新型的杀虫、杀螨和杀线虫的芳基吡咯烷类药剂，以及一种通过使用这些药剂来控制昆虫、螨虫和线虫的方法。该发明还涉及一种通过向生长中的植物或其生长的土壤施加一定量的新型芳基吡咯烷类化合物来保护植物免受昆虫、螨虫和线虫侵害的方法。本发明还涉及一种制备芳基吡咯烷类化合物的方法。

表征谱图