2-hydroxymethylenetestosterone | 131831-23-7

• 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: 2-hydroxymethylenetestosterone
• 英文别名: (2Z,8R,9S,10R,13S,14S,17S)-17-hydroxy-2-(hydroxymethylidene)-10,13-dimethyl-6,7,8,9,11,12,14,15,16,17-decahydro-1H-cyclopenta[a]phenanthren-3-one
• CAS: 131831-23-7
• 化学式: C₂₀H₂₈O₃
• 分子量: 316.441
• InChiKey: WBQHPGBBOIFJLF-BLUUCWDVSA-N

物化性质

• 沸点：
  488.3±45.0 °C(Predicted)
• 密度：
  1.19±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.7
• 重原子数：
  23
• 可旋转键数：
  0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.75
• 拓扑面积：
  57.5
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  2-hydroxymethylenetestosterone 在 对甲苯磺酸 作用下， 以 二苯醚 为溶剂， 反应 0.5h， 生成 5'-deaza-17β-hydroxy-8'-methyl-5α-androst-2-eno[2,3-g]pteridine-2',4'(3'H,8'H)dione
  参考文献：
  名称：

  New Synthesis and Biologically Active Molecular Design of Deazapteridine-Steroid Hybrid Compounds

  摘要：

  This paper describes a facile and general synthesis of a new class of the hybrid compounds (4, 5 and 16), possessing 5-deazapteridine and steroid in the same ring system, by condensation of 6-(monosubstituted amino)uracils (9) or 6-(monosubstituted amino)-2-phenylpyrimidin-4(3H)-ones (14) with 2-hydroxymethyleneandrostanolone (10) or 2-hydroxymethylenetestosterone (15) under heating in the presence of p-toluenesulfonic acid monohydrate and their potential unti-coccidiosis activities.

  DOI：

  10.3987/com-03-9925

文献信息

• Keto/Enol Epoxy Steroids as HIV-1 Tat Inhibitors: Structure-Activity Relationships and Pharmacophore Localization
  作者：William F. Michne、Joseph D. Schroeder、Thomas R. Bailey、Helmut C. Neumann、Debra Cooke、Dorothy C. Young、Joseph V. Hughes、Susan D. Kingsley、Kathryn A. Ryan、Henry S. Putz、Lucinda J. Shaw、Frank J. Dutko

  DOI：10.1021/jm00017a003

  日期：1995.8

  Inhibition of the HIV-1 nuclear regulatory protein tat could potentially yield particularly useful drugs because it functions as an activator of transcription. It has no known cellular counterpart, and deletions in the tat gene destroy the ability of HIV-1 to replicate. We recently reported that a structurally unique class of tat inhibitors, 3-keto/enol 4,5-alpha-epoxy steroids bearing electron-withdrawing

  抑制HIV-1核调节蛋白tat可能会产生特别有用的药物，因为它起着转录激活剂的作用。它没有已知的细胞对应物，并且tat基因的缺失破坏了HIV-1复制的能力。我们最近报道，在结构上独特的一类tat抑制剂，在位置2带有吸电子取代基的3-酮/烯醇4,5-α-环氧类固醇，在无病毒转染的SW480细胞中特异性抑制tat诱导的基因表达。在本文中，我们报告了类固醇系列的其他SAR（结构-活性关系）和药效团定位于A环功能的情况。对天然类固醇立体化学的对映选择性偏弱，并且在吸电子基团中存在额外的SAR提示。
• Sequential Addition/Elimination/Annulation Reactions of 4-Pentynones with Benzylamine and Ammonia
  作者：Antonio Arcadi、Elisabetta Rossi

  DOI：10.1055/s-1997-3242

  日期：1997.6

  The sequential addition/elimination/cycloammination of 4-pentynones in the presence of benzylamine or ammonia produces 1,2,3,-5-substituted and 2,3,5-substituted pyrroles and fused pyrrole systems, respectively in good to high yields. The methodology has been extended to the preparation of the 17β-hydroxyandrost-4-ene[3,2-b](1-benzyl-5-methyl)pyrrole.

  在苄胺或氨存在下，4-戊炔酮依次加成/消除/环氨基化，分别生成 1,2,3,-5 取代和 2,3,5 取代的吡咯和融合的吡咯系统，收率从好到高。该方法已扩展到 17δ²-羟基雄甾-4-烯[3,2-b](1-苄基-5-甲基)吡咯的制备。
• New steroidal heterocycles: the synthesis and structure of androsteno[2,3-g]-, androstano[3,2-f]-, and androsteno[16,17-g]-pyrazolo[1,5-a]pyrimidines
  作者：Joginder S. Bajwa、Peter J. Sykes

  DOI：10.1039/p19800000481

  日期：——

  fused and linearly fused products, androst-2-eno[2,3-g]- and androstano[3,2-f]-pyrazolo[1,5-a]pyrimidines, respectively. However, the condensation of 3-amino-4-cyano-5-cyanomethylpyrazole with 2-hydroxymethyl-3-oxo-steroids gave only angularly fused products, namely, androst-2-eno[2,3-g]pyrazolo[1,5-a]pyrimidines. The reaction of 3-aminopyrazole and its derivatives with a 2-hydroxymethylene-Δ4-3-oxosteroid

  3-氨基吡唑及其4-氰基衍生物与2-羟基亚甲基-3-氧代甾族化合物的反应，得到了角熔合和线性熔合产物的混合物，其中rost-2-eno [2,3- g ]-和androstano [ 3，2- f ]-吡唑并[1，5- a ]嘧啶。然而，3-氨基-4-氰基-5-氰基甲基吡唑与2-羟甲基-3-氧代甾族化合物的缩合仅产生有角度的熔融产物，即，rost-2-eno [2,3- g ] pyrazolo [1， 5- α ]嘧啶。3-氨基吡唑和反应及其与2-羟基亚甲基-Δ衍生物4 -3- oxosteroid和16羟基亚甲基-17-氧代-甾族化合物也得到只有角度熔融产物，雄甾-2,4-二烯并[2,3 -克]-和androst-16-eno [16,17- g ]-吡唑并[1,5- a ]嘧啶。所有这些化合物的结构都是通过ir，uv，1 H和13 C nmr光谱确定的。
• 20-Fluoro-17(20)-vinyl steroids
  申请人：——

  公开号：US20020019548A1

  公开（公告）日：2002-02-14

  The invention related to 20&xgr;-fluoropregna-4,17(20)-dien-3-on-21-oic acid ethyl ester, 20&xgr;-fluoro-3&bgr;-hydroxypregna-4,17(20)-dien-21-oic acid ethyl ester, 20&xgr;-fluoro-21-hydroxypregna-4,17(20)-dien-3-one, 20&xgr;-fluoropregna-4,17(20)-dien-3&bgr;,21-diol and related compounds and to compositions incorporating these compounds, as well as the inhibition of C 17,20 lyase, 5&agr;-reductase and C 17 -hydroxylase, and to the use of these compounds in the treatment of androgen and estrogen mediated or dependent disorders, including benign prostatic hyperplasia, prostate cancer, breast cancer and DHT-mediated disorders such as acne and hirsutism. Treatment of disorders related to the over synthesis of cortisol, for example, Cushing's Syndrome are also included. The treatment of androgen-dependent disorders also includes a combination therapy with known androgen-receptor antagonists, such as flutamide. The compounds of the invention have the following general formulae: 1

  本发明涉及20&xgr;-氟孕-4,17（20）-二烯-3-酮-21-羧酸乙酯，20&xgr;-氟-3&bgr;-羟基孕-4,17（20）-二烯-21-羧酸乙酯，20&xgr;-氟-21-羟基孕-4,17（20）-二烯-3-酮，20&xgr;-氟孕-4,17（20）-二烯-3&bgr;，21-二醇及其相关化合物，以及包含这些化合物的组合物，以及抑制C17,20裂解酶、5&agr;-还原酶和C17-羟化酶，并将这些化合物用于治疗雄激素和雌激素介导或依赖性疾病，包括良性前列腺增生症、前列腺癌、乳腺癌和DHT介导的疾病，如痤疮和多毛症。本发明还包括治疗与皮质醇过度合成有关的疾病，例如库欣综合征。雄激素依赖性疾病的治疗还包括与已知雄激素受体拮抗剂（如氟他胺）的联合治疗。本发明的化合物具有以下一般式：1
• USE OF COENZYME FACTOR FOR ACTIVATION OF ATP PRODUCTION IN CELL
  申请人：Tera Stone Co., Ltd

  公开号：EP3750543A1

  公开（公告）日：2020-12-16

  Problem: to provide an activator for activating intracellular ATP production. Solution: use of a 5-deazaflavin compound represented by the following formula (I): (wherein, R1 represents a hydrogen atom, an alkyl group, a halogen-substituted alkyl group, a carboxy-substituted alkyl group, or a phenyl group, R2 represents an alkyl group, a cycloalkyl group, a phenyl-substituted lower alkyl group, a phenyl group, a phenyl group substituted by one of a halogen atom, a lower alkyl group, or a lower alkoxy group, or a lower alkyl disubstituted phenyl group, and R3 and R4 each represent a hydrogen atom, a lower alkyl group, a halogen atom, a hydroxyl group, a nitro group, a cyano group, a lower alkoxy group, a phenyl-substituted lower alkoxy, a lower alkylamino group, a phenyl-substituted lower alkylamino group, or a lower alkylsulfonyl group).

  问题：提供一种激活细胞内 ATP 生成的激活剂。解决方案：使用由下式（I）代表的 5-脱氮黄素化合物： (其中，R1 代表氢原子、烷基、卤素取代的烷基、羧基取代的烷基或苯基，R2 代表烷基、环烷基、苯基取代的低级烷基、苯基、被卤素原子、低级烷基或低级烷氧基之一取代的苯基、或低级烷基二取代苯基，且 R3 和 R4 各自代表氢原子、低级烷基、卤素原子、羟基、硝基、氰基、低级烷氧基、苯基取代的低级烷氧基、低级烷基氨基、苯基取代的低级烷基氨基或低级烷基磺酰基）。