21-乙酰氧基孕烯醇酮 | 566-78-9

• 物质功能分类: 有机原料 - 酮类化合物
• 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: 21-乙酰氧基孕烯醇酮
• 中文别名: 酒石酸苯茚胺
• 英文名称: 21-acetoxypregnenolone
• 英文别名: [2-[(3S,8S,9S,10R,13S,14S,17S)-3-hydroxy-10,13-dimethyl-2,3,4,7,8,9,11,12,14,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthren-17-yl]-2-oxoethyl] acetate
• CAS: 566-78-9
• 化学式: C₂₃H₃₄O₄
• 分子量: 374.521
• InChiKey: MDJRZSNPHZEMJH-MTMZYOSNSA-N

物化性质

• 溶解度：
  可溶于氯仿（少许）、甲醇（少许）

计算性质

• 辛醇/水分配系数(LogP)：
  4.1
• 重原子数：
  27
• 可旋转键数：
  4
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.83
• 拓扑面积：
  63.6
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  21-乙酰氧基孕烯醇酮 在 氧气 、 potassium carbonate 作用下， 以 四氢呋喃 、 甲醇 为溶剂， 以55%的产率得到3-羟基-10,13-二甲基-2,3,4,7,8,9,11,12,14,15,16,17-十二氢-1H-环戊二烯并[a]菲-17-羧酸
  参考文献：
  名称：

  A new steroidal 5,7-diene derivative, 3β-hydroxyandrosta-5,7-diene-17β-carboxylic acid, shows potent anti-proliferative activity

  摘要：

  The new steroidal 5,7-diene, 3 beta-hydroxyandrosta-5,7-diene-17 beta-carboxylic acid (17-COOH-7DA), was synthesized from 21-acetoxypregnenolone, with the oxidative cleavage of the side chain being dependent on the presence of oxygen. In human epidermal (HaCaT) keratinocytes, 17-COOH-7DA inhibited proliferation in a close-dependent manner, starting at a dose as low as 10(-11) M. This inhibition was accompanied by decreased expression of epidermal growth factor receptor, bcl2 and cyclin E2 mRNAs and by increased expression of involucrin mRNA. Inhibition of proliferation was associated with slowing of the cell cycle in G1/G0 phases but not with cell death. 17-COOH-7DA was significantly more potent than pregnenolone, 17-COOH-pregnenolone, 17-COOCH(3)-7DA and calcitriol. 17-COOH-7DA also inhibited proliferation of normal human epidermal melanocytes and human and hamster melanoma lines, however, with lower potency than for keratinocytes. In normal human dermal fibroblasts 17-COOH-7DA stimulated proliferation in serum-free media but inhibited it in the presence of 5% serum. 17-COOH-7DA inhibited cell colony formation of human and hamster melanoma cells, and induced monocyte-like differentiation of human HL60 leukemia cells. Thus, the new steroidal 5,7-diene, 17-COOH-7DA, can serve as an inhibitor of proliferation of normal keratinocytes and normal and malignant melanocytes, as a condition-dependent regulator of fibroblast proliferation and a stimulator of leukemia cell differentiation. (C) 2009 Elsevier Inc. All rights reserved.

  DOI：

  10.1016/j.steroids.2009.12.004
• 作为产物：
  描述：

  孕烯醇酮 在 N-碘代丁二酰亚胺 、 氟化氢吡啶 、 三乙胺 作用下， 以 二氯甲烷 、 丙酮 为溶剂， 反应 28.0h， 生成 21-乙酰氧基孕烯醇酮
  参考文献：
  名称：

  氟取代对细胞色素 P450 17A1 和 21A2 底物转化的影响

  摘要：

  细胞色素 P450 17A1 (CYP7A1) 和 21A2 (CYP21A2) 催化类固醇激素（包括盐皮质激素、糖皮质激素和雄激素）生成中的关键反应。最终目标是设计选择性代谢每种类固醇类型的探针，准备内源性底物孕烯醇酮和黄体酮的氟化衍生物来研究对 CYP17A1 和 CYP21A2 活性的影响。在功能测定中，当在代谢位点（分别为类固醇核心的位置 17 和 21）引入氟时，这些酶催化的羟化酶反应都会被阻断。此外，CYP17A1 在 21 位安装有氟的底物上进行 17,20-裂解酶反应。重要的是，如光谱结合测定所证明的，本文检查的取代均未阻止化合物进入 CYP17A1 或 CYP21A2 的活性位点。综上所述，结果表明氟可能用于将孕烯醇酮和黄体酮的代谢途径重定向至特定类型的类固醇。

  DOI：

  10.1039/d1ob01178b

文献信息

• [EN] DIPEPTIDE AND TRIPEPTIDE EPOXY KETONE PROTEASE INHIBITORS<br/>[FR] INHIBITEURS DE DIPEPTIDE ET DE TRIPEPTIDE ÉPOXY CÉTONE PROTÉASES
  申请人：ONYX THERAPEUTICS INC

  公开号：WO2014152127A1

  公开（公告）日：2014-09-25

  Provided herein are dipeptide and tripeptide epoxy ketone protease inhibitors, methods of their preparation, related pharmaceutical compositions, and methods of using the same. For example, provided herein are compounds of Formula (X): and pharmaceutically acceptable salts and compositions including the same. The compounds and compositions provided herein may be used, for example, in the treatment of proliferative diseases including cancer and autoimmune diseases.

  本文提供了二肽和三肽环氧酮蛋白酶抑制剂，其制备方法，相关的药物组合物，以及使用它们的方法。例如，本文提供了化合物的化学式（X）：及其药用盐和包括这些化合物的组合物。本文提供的化合物和组合物可以用于治疗增生性疾病，包括癌症和自身免疫疾病。
• BICYCLIC HETEROARYL COMPOUNDS AND USES THEREOF
  申请人：Revolution Medicines, Inc.

  公开号：US20210139517A1

  公开（公告）日：2021-05-13

  The present disclosure is directed to modulators of SOS1 and their use in the treatment of disease. Also disclosed are pharmaceutical compositions comprising the same.

  本公开涉及SOS1的调节剂及其在治疗疾病中的应用。还公开了包含相同成分的药物组合物。
• [EN] ISOTHIAZOLOQUINOLONES AND RELATED COMPOUNDS AS ANTI-INFECTIVE AGENTS<br/>[FR] ANTI-INFECTIEUX A BASE D'ISOTHIAZOLOQUINOLONES ET DE SELS CORRESPONDANTS
  申请人：ACHILLION PHARMACEUTICALS INC

  公开号：WO2005019228A1

  公开（公告）日：2005-03-03

  The invention provides compounds and salts of Formula (I) and Formula (II): which possess antimicrobial activity. The invention also provides novel synthetic intermediates useful in making compounds of Formula (I) and Formula (II). The variables A1, R2, R3, R5, R6, R7, A8 and R9 are defined herein. Certain compounds of Formula (I) and Formula (II) disclosed herein are potent and selective inhibitors of bacterial DNA synthesis and bacterial replication. The invention also provides antimicrobial compositions, including pharmaceutical compositions, containing one or more compounds of Formula (I) or Formula (II) and one or more carriers, excipients, or diluents. Such compositions may contain a compound of Formula (I) or Formula (II) as the only active agent or may contain a combination of a compound of Formula (I) or Formula (II) and one or more other active agents. The invention also provides methods for treating microbial infections in animals.

  本发明提供了具有抗菌活性的公式(I)和公式(II)的化合物及盐类：本发明还提供了用于制造公式(I)和公式(II)化合物的新的合成中间体。变量A1、R2、R3、R5、R6、R7、A8和R9在此文中定义。本文披露的某些公式(I)和公式(II)化合物是细菌DNA合成和细菌复制的强效和选择性抑制剂。本发明还提供了含有一种或多种公式(I)或公式(II)化合物以及一种或多种载体、辅料或稀释剂的抗菌组合物，包括药物组合物。这样的组合物可以只含有公式(I)或公式(II)的化合物作为唯一的活性成分，也可以含有公式(I)或公式(II)的化合物与一种或多种其他活性成分的组合。本发明还提供了用于治疗动物微生物感染的方法。
• [EN] MONO AND BICYCLIC RING BORONIC ACID, ESTER AND SALT COMPOUNDS AS INHIBITORS OF P97 COMPLEX<br/>[FR] COMPOSÉS D'ESTER, DE SEL ET D'ACIDE BORONIQUE À NOYAU MONOCYCLIQUE ET BICYCLIQUE EN TANT QU'INHIBITEURS DE COMPLEXE P97
  申请人：CLEAVE BIOSCIENCES INC

  公开号：WO2016200840A1

  公开（公告）日：2016-12-15

  Monocyclic or bicyclic ring boronic acid or ester compounds having an arylalkyi amine substituent at the 4 position and a substituted 5:6 bicyclic group at the 2 position of the mono or bicyclic ring boronic acid or ester as well as optional aliphatic, functional and/or aromatic components substituted at other positions of the mono or bicyclic boronic acid or ester compounds are disclosed. These compounds are inhibitors of the AAA proteasome complex containing p97 and are effective medicinal agents for treatment of diseases associated with the Valosin containing protein and p97 bioactivity such as cancer. Formula (I).

  单环或双环硼酸或硼酸酯化合物，在4位具有芳烷基胺取代基，在单环或双环硼酸或硼酸酯的2位具有取代的5:6双环基团，以及在单环或双环硼酸或硼酸酯化合物的其他位置可选地取代有脂肪族、功能性和/或芳香族组分。这些化合物是含有p97的AAA蛋白酶体的抑制剂，并且是治疗与含有Valosin蛋白和p97生物活性相关的疾病的有效药物，如癌症。公式(I)。
• FORMULATIONS FROM NATURAL PRODUCTS, TURMERIC, PACLITAXEL, AND ASPIRIN
  申请人：Jacob James N.

  公开号：US20150250844A1

  公开（公告）日：2015-09-10

  The invention provides novel compounds and formulations of turmeric oil, fish oil, aspirin and anti-cancer drugs (paclitaxel) having anti-inflammatory, analgesic and/or anti-cancer activity.

  本发明提供了具有抗炎、镇痛和/或抗癌活性的姜油、鱼油、阿司匹林和抗癌药物（紫杉醇）的新化合物和配方。