2-<5-<<(tert-butyldimethylsilyl)oxy>methyl>pyridin-2-yl>benzonitrile | 145733-55-7

• 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: 2-<5-<<(tert-butyldimethylsilyl)oxy>methyl>pyridin-2-yl>benzonitrile
• 英文别名: 2-(5-(((tert-butyldimethylsilyl)oxy)methyl)pyridin-2-yl)benzonitrile；2-[5-(tert-butyldimethylsilyloxymethyl)pyridin-2-yl]benzonitrile；2-[5-(Tert-butyldimethylsiloxymethyl)pyridin-2-yl]benzonitrile；2-[5-[[tert-butyl(dimethyl)silyl]oxymethyl]pyridin-2-yl]benzonitrile
• CAS: 145733-55-7
• 化学式: C₁₉H₂₄N₂OSi
• 分子量: 324.498
• InChiKey: YKFNTABAUAUVBE-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.14
• 重原子数：
  23
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.37
• 拓扑面积：
  45.9
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  2-<5-<<(tert-butyldimethylsilyl)oxy>methyl>pyridin-2-yl>benzonitrile 在 氯化亚砜 、 四丁基氟化铵 、 sodium hydride 、 zinc(II) chloride 作用下， 以 四氢呋喃 、 1,4-二氧六环 为溶剂， 反应 41.0h， 生成 2-Methyl-4-trifluoromethyl-5,6,8-trihydro-8-[[6-(2-cyanophenyl)-3-pyridinyl]methyl]-7H-pyrido[2,3-d]pyrimidin-7-one
  参考文献：
  名称：

  Pyrido[2,3-d]pyrimidine Angiotensin II Antagonists

  摘要：

  A series of pyrido[2,3-d]pyrimidine angiotensin II (A II) antagonists was synthesized and tested for antagonism of A II. Compounds with a biphenylyltetrazole pharmacophore and small alkyl groups at the 2- and ii-positions Of the pyridopyrimidine ring were found to be the most potent in an AT(1) receptor binding assay and in blocking the A II presser response in anesthetized, ganglion-blocked A II-infused rats. 5,8-Dihydro-2,4-dimethyl-8-[(2'-(1H-tetrazol-5-yl)[1,1'-biphenyl]-4-yl)methyl] pyrido[2,3-d]pyrimidin-7(6H)-one (4a) was one of the more potent compounds in the binding assay and was the most efficacious compound in the A II-infused rat model. Further study of 4a;in Goldblatt (2K-1C) rats showed the compound to have oral bioavailability and to be an efficacious and potent compound in a high renin form of hypertension.

  DOI：

  10.1021/jm00030a013
• 作为产物：
  描述：

  6-溴烟酸 在 copper(l) iodide 、 正丁基锂 、 bis(triphenylphosphine)palladium(II)-chloride 、 硼烷 、 三丁基氯化锡 作用下， 以 四氢呋喃 、 N,N-二甲基甲酰胺 为溶剂， 反应 4.0h， 生成 2-<5-<<(tert-butyldimethylsilyl)oxy>methyl>pyridin-2-yl>benzonitrile
  参考文献：
  名称：

  Pyrido[2,3-d]pyrimidine Angiotensin II Antagonists

  摘要：

  A series of pyrido[2,3-d]pyrimidine angiotensin II (A II) antagonists was synthesized and tested for antagonism of A II. Compounds with a biphenylyltetrazole pharmacophore and small alkyl groups at the 2- and ii-positions Of the pyridopyrimidine ring were found to be the most potent in an AT(1) receptor binding assay and in blocking the A II presser response in anesthetized, ganglion-blocked A II-infused rats. 5,8-Dihydro-2,4-dimethyl-8-[(2'-(1H-tetrazol-5-yl)[1,1'-biphenyl]-4-yl)methyl] pyrido[2,3-d]pyrimidin-7(6H)-one (4a) was one of the more potent compounds in the binding assay and was the most efficacious compound in the A II-infused rat model. Further study of 4a;in Goldblatt (2K-1C) rats showed the compound to have oral bioavailability and to be an efficacious and potent compound in a high renin form of hypertension.

  DOI：

  10.1021/jm00030a013

文献信息

• Rhodium(<scp>iii</scp>)-catalyzed aromatic C–H cyanation with dimethylmalononitrile as a cyanating agent
  作者：He Li、Sheng Zhang、Xiaoqiang Yu、Xiujuan Feng、Yoshinori Yamamoto、Ming Bao

  DOI：10.1039/c8cc08930b

  日期：——

  A rhodium-catalyzed aromatic C–H bond direct cyanation with safe, bench-stable, and commercially available dimethylmalononitrile as the cyanating agent has been successfully developed by using copper oxide as a promotor. Pyridine, quinoline, pyrimidine and pyrazole were used as the directing group in this type of C–H bond direct cyanation reaction.

  通过使用氧化铜作为促进剂，成功开发出了铑催化的芳香族CH键直接氰化，安全，稳定和可商购的二甲基丙二腈作为氰化剂。吡啶，喹啉，嘧啶和吡唑被用作这种C–H键直接氰化反应的导向基团。
• Substituted pyridopyrimidines useful as antgiotensin II antagonists
  申请人：American Home Products Corporation

  公开号：US05149699A1

  公开（公告）日：1992-09-22

  This invention relates to pyrrolo-, pyrido-, azepino-, and azocinopyrimidines of the general formula I ##STR1## useful for treating hypertension and congestive heart failure, to pharmaceutical compositions, and to methods for production thereof.

  本发明涉及一般式I的吡咯、吡啶、氮杂环庚烷和氮杂环癸烷并咪唑啉，其用于治疗高血压和充血性心力衰竭，药物组成和生产方法。
• Substituted pyrrolopyrimidines and pyridopyrimidines useful as
  申请人：American Home Products Corporation

  公开号：US05498776A1

  公开（公告）日：1996-03-12

  This invention relates to pyrrolo-, pyrido-, azepino-, and azocinopyrimidines of the general formula I ##STR1## wherein R.sup.1, R.sup.2, R.sup.3, and R.sup.4 are independently H, lower alkyl containing 1 to 6 carbon atoms, or perfluoroalkyl containing 1 to 6 carbon atoms; R.sup.5 is H or, when n is 1, R.sup.5 taken together with R.sup.3 comprises a double bond, n is 0 or 1, p is 0 to 2, m is 0 to 3; Ar.sup.1 is ##STR2## wherein W is H, lower alkyl containing 1 to 6 carbon atoms, halogen, hydroxy, or lower alkoxy containing 1 to 6 carbon atoms; and Ar.sup.2 is ##STR3## wherein X is ##STR4## wherein R.sup.6 is H, tert-butyl, tri-n-butylstannyl, or triphenylmethyl; and the pharmaceutically acceptable salts thereof, which compounds are useful in the treatment of hypertension and congestive heart failure.

  本发明涉及一般式I的吡咯烷、吡啶烷、氮杂环庚烷和氮杂环壬烷基嘧啶类化合物，其中R1、R2、R3和R4分别独立地为H、含有1至6个碳原子的低碳烷基或含有1至6个碳原子的全氟烷基；R5为H或当n为1时，R5与R3结合成双键；n为0或1；p为0至2；m为0至3；Ar1为##STR2##其中W为H、含有1至6个碳原子的低碳烷基、卤素、羟基或含有1至6个碳原子的低碳基氧基；Ar2为##STR3##其中X为##STR4##其中R6为H、叔丁基、三正丁基锡基或三苯基甲基；以及其药学上可接受的盐，这些化合物在治疗高血压和充血性心力衰竭方面有用。
• Ellingboe John W., Antane Madelene, Nguyen Thomas T., Collini Michael D.,+, J. Med. Chem, 37 (1994) N 4, S 542-550
  作者：Ellingboe John W., Antane Madelene, Nguyen Thomas T., Collini Michael D.,+

  DOI：——

  日期：——
• Pyrido[2,3-d]pyrimidine Angiotensin II Antagonists
  作者：John W. Ellingboe、Madelene Antane、Thomas T. Nguyen、Michael D. Collini、Schuyler Antane、Reinhold Bender、Dale Hartupee、Valerie White、John McCallum

  DOI：10.1021/jm00030a013

  日期：1994.2

  A series of pyrido[2,3-d]pyrimidine angiotensin II (A II) antagonists was synthesized and tested for antagonism of A II. Compounds with a biphenylyltetrazole pharmacophore and small alkyl groups at the 2- and ii-positions Of the pyridopyrimidine ring were found to be the most potent in an AT(1) receptor binding assay and in blocking the A II presser response in anesthetized, ganglion-blocked A II-infused rats. 5,8-Dihydro-2,4-dimethyl-8-[(2'-(1H-tetrazol-5-yl)[1,1'-biphenyl]-4-yl)methyl] pyrido[2,3-d]pyrimidin-7(6H)-one (4a) was one of the more potent compounds in the binding assay and was the most efficacious compound in the A II-infused rat model. Further study of 4a;in Goldblatt (2K-1C) rats showed the compound to have oral bioavailability and to be an efficacious and potent compound in a high renin form of hypertension.