adamantane-1-carboxylic acid pyridin-4-ylmethyl ester

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡啶及其衍生物
• 英文名称: adamantane-1-carboxylic acid pyridin-4-ylmethyl ester
• 英文别名: 4-Pyridylmethyl 1-adamantanecarboxylate；pyridin-4-ylmethyl adamantane-1-carboxylate
• 化学式: C₁₇H₂₁NO₂
• 分子量: 271.359
• InChiKey: BUVUAMDJGFSXDF-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  20
• 可旋转键数：
  4
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.65
• 拓扑面积：
  39.2
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  4-吡啶甲醇 、 金刚烷酰氯 在 正丁基锂 作用下， 以 四氢呋喃 、 正己烷 为溶剂， 以35%的产率得到adamantane-1-carboxylic acid pyridin-4-ylmethyl ester
  参考文献：
  名称：

  Pyridyl-propan-2-yl esters of 1-adamantane carboxylates

  摘要：

  具有以下通式的化合物：##STR1## 其中R.sup.1和R.sup.2各自代表氢或1至4个碳原子的烷基；A代表--O--或--CR.sup.4 R.sup.5，其中R.sup.4和R.sup.5的定义与R.sup.1或R.sup.2相同；R.sup.3代表脱氢环戊基团；Py代表3-或4-吡啶基团，作为自由碱或其药用盐，对治疗依赖雄激素的，特别是前列腺癌有益。

  公开号：

  US05595995A1

文献信息

• 3- and 4-Pyridylalkyl Adamantanecarboxylates:  Inhibitors of Human Cytochrome P450₁₇_α <b>(17</b>α-Hydroxylase/C_17,20-Lyase). Potential Nonsteroidal Agents for the Treatment of Prostatic Cancer
  作者：Ferdinand C. Y. Chan、Gerard A. Potter、S. Elaine Barrie、Benjamin P. Haynes、Martin G. Rowlands、John Houghton、Michael Jarman

  DOI：10.1021/jm950749y

  日期：1996.1.1

  Various 3- and 4-pyridylalkyl 1-adamantanecarboxylates have been synthesized and tested for inhibitory activity toward the 17 alpha-hydroxylase and C-17,C-20-lyase activities of human testicular cytochrome P450(17 alpha). The 4-pyridylalkyl esters were much more inhibitory than their 3-pyridylalkyl counterparts. The most potent was (S)-1-(4-pyridyl)ethyl 1-adamantanecarboxylate (3b; IC50 for lyase, 1.8 nM), whereas the (R)-enantiomer 3a was much less inhibitory (IC50 74 nM). Nearly as potent as 3b was the dimethylated counterpart, the 2-(4-pyridylpropan-2-yl) ester 5 (IC50 2.7 nM), which was also more resistant to degradation by esterases. In contrast to their 4-pyridyl analogs, the enantiomers of the 1-(3-pyridyl)ethyl ester were similarly inhibitory (IC50 for lyase; (R)-isomer 8a 150 nM, (S)-isomer 8b 230 nM). Amides corresponding to the 4-pyridylmethyl ester 1 and the (S)-1-(4-pyridyl)ethyl ester 3b, respectively 11 and 15b, were much less inhibitory than their ester counterparts. On the basis of a combination of inhibitory potency and resistance to esterases, the ester 5 was the best candidate for further development as a potential nonsteroidal inhibitor of cytochrome P450(17 alpha), for the treatment of prostate cancer.
• Superacid-catalyzed reactions of pyridinecarboxaldehydes
  作者：Douglas A. Klumpp、Yiliang Zhang、Patrick J. Kindelin、Siufu Lau

  DOI：10.1016/j.tet.2006.04.022

  日期：2006.6

  A variety of pyridinecarboxaldehydes are shown to give condensation products in high yields (80-99%, 10 examples) by reacting with benzene and CF3SO3H (triflic acid). In the superacidic solution, pyridinecarboxaldehydes can react with deactivated arenes (o-dichlorobenzene and nitrobenzene) and with saturated hydrocarbons (methylcyclohexane and adamantane). Dicationic intermediates from pyridinecarboxaldehydes in superacid (FSO3H-SbF5) have been directly observed using low temperature C-13 NMR spectroscopy. Diprotonated pyridinecarboxaldehydes have also been studies using ab initio computational methods. (c) 2006 Elsevier Ltd. All rights reserved.
• Derivatives of pyridine as hydroxylase and lyase inhibitors
  申请人：BTG INTERNATIONAL LIMITED

  公开号：EP0640072B1

  公开（公告）日：2000-08-23
• US5595995A
  申请人：——

  公开号：US5595995A

  公开（公告）日：1997-01-21
• [EN] SUBSTITUTED PYRIDINES, THEIR PREPARATION AND PHARMACEUTICAL USE<br/>[FR] PYRIDINES SUBSTITUEES, LEUR PREPARATION ET LEUR UTILISATION PHARMACEUTIQUE
  申请人：BRITISH TECHNOLOGY GROUP LIMITED

  公开号：WO1993023375A1

  公开（公告）日：1993-11-25

  (EN) Compounds having general formula: (3) wherein each of R1 and R2 independently represents hydrogen or alkyl of 1 to 4 carbon atoms; A represents -O- or -CR4R5, where R4 and R5 are defined as for R1 or R2; R3 represents an adamantyl group; and Py represents a 3- or 4-pyridyl group, as free bases or their pharmaceutically acceptable salts are useful in treating androgen-dependent, especially prostatic, cancer.(FR) Composés répondant à la formule générale (3): dans laquelle R1 et R2 représentent chacun indépendamment hydrogène ou alkyle contenant de 1 à 4 atomes de carbone; A représente -O- ou -CR4R5, R4 et R5 étant définis comme R1 ou R2; R3 représente un groupe adamantyle; et Py représente un groupe 3- ou 4-pyridyle. Ces composés, sous forme de bases libres, ou leurs sels pharmaceutiquement acceptables peuvent être utilisés pour traiter le cancer dépendant de l'androgène, en particulier le cancer prostatique.