3-Pyridylmethyl 1-adamantanecarboxylate

• 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: 3-Pyridylmethyl 1-adamantanecarboxylate
• 英文别名: Adamantane-1-carboxylic acid pyridin-3-ylmethyl ester；pyridin-3-ylmethyl adamantane-1-carboxylate
• 化学式: C₁₇H₂₁NO₂
• 分子量: 271.359
• InChiKey: NRWFQUHIGJOJDH-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：

  3-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78%的产率得到3-Pyridylmethyl 1-adamantanecarboxylate
  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

• Pyridyl-propan-2-yl esters of 1-adamantane carboxylates
  申请人：British Technology Group Limited

  公开号：US05595995A1

  公开（公告）日：1997-01-21

  Compounds having the general formula: ##STR1## wherein each of R.sup.1 and R.sup.2 independently represents hydrogen or alkyl of 1 to 4 carbon atoms; A represents --O-- or --CR.sup.4 R.sup.5, where R.sup.4 and R.sup.5 are defined as for R.sup.1 or R.sup.2 ; R.sup.3 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.

  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。
• Ruthenium pincer complex-catalyzed heterocycle compatible alkoxycarbonylation of alkyl iodides: substrate keeps the catalyst active
  作者：Han-Jun Ai、Yang Yuan、Xiao-Feng Wu

  DOI：10.1039/d1sc06581e

  日期：——

  the heteroatom in heterocycles will coordinate with metal catalysts and decrease or even inhibit their catalytic activity consequently. In this work, a pincer ruthenium-catalyzed heterocycle compatible alkoxycarbonylation of alkyl iodides has been developed. Benefitting from the pincer ligand, a variety of heterocycles, such as thiophenes, morpholine, unprotected indoles, pyrrole, pyridine, pyrimidine

  杂环中杂原子的电子对会与金属催化剂配位，从而降低甚至抑制其催化活性。在这项工作中，开发了一种钌催化的烷基碘化物的杂环相容性烷氧基羰基化反应。受益于钳配体，多种杂环，例如噻吩、吗啉、未保护的吲哚、吡咯、吡啶、嘧啶、呋喃、噻唑、吡唑、苯并噻二唑和三唑在这里是相容的。
• 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
• 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.