N-(2-hydroxy-1,1-dimethylethyl)-2-biphenylcarboxamide | 69381-38-0

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: N-(2-hydroxy-1,1-dimethylethyl)-2-biphenylcarboxamide
• 英文别名: N-(1-hydroxy-2-methylpropan-2-yl)-2-phenylbenzamide
• CAS: 69381-38-0
• 化学式: C₁₇H₁₉NO₂
• 分子量: 269.343
• InChiKey: DSRHQEFKYDDXOK-UHFFFAOYSA-N

物化性质

• 沸点：
  475.4±38.0 °C(Predicted)
• 密度：
  1.112±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  20
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.24
• 拓扑面积：
  49.3
• 氢给体数：
  2
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  N-(2-hydroxy-1,1-dimethylethyl)-2-biphenylcarboxamide 在 氯化亚砜 作用下， 以 甲苯 为溶剂， 反应 48.0h， 以78%的产率得到2-(2-Biphenyl)-4,4-dimethythyl-2-oxazoline
  参考文献：
  名称：

  Mazindol Analogues as Potential Inhibitors of the Cocaine Binding Site at the Dopamine Transporter

  摘要：

  A series of mazindol. (2) and homomazindol (3) analogues with a variety of electron-donating and electron-withdrawing groups in the pendant aryl group and the benzo ring C, as well as H, methoxy, and alkyl groups replacing the hydroxyl group were synthesized, and their binding affinities at the dopamine transporter (DAT) on rat or guinea pig striatal. membranes were determined. Several active analogues were also evaluated for their ability to block uptake of DA, 5-HT, and NE and inhibit binding of [I-125] RTI-55 at HEK-hDAT, HEK-hSERT, and HEK-hNET cells. Mazindane (26) was found to be a pro-drug, oxidizing (5-H --> 5-OH) to mazindol on rat striatal membranes and HEk-hDAT cells. The 4',7,8-trichloro analogue (38) of mazindol was the I most potent and selective ligand. for HEK-hDAT cells (DAT K-i = 1.1 nM; SERT/DAT 1283 and NET/DAT = 38). Experimental results strongly favor the cyclic or ol tautomers of 2 and 3 to bind more, tightly at the DAT than the corresponding keto tautomers.

  DOI：

  10.1021/jm010302r
• 作为产物：
  描述：

  2-苯基苯甲酰氯 、 2-氨基-2-甲基-1-丙醇 以 二氯甲烷 为溶剂， 反应 24.0h， 以68%的产率得到N-(2-hydroxy-1,1-dimethylethyl)-2-biphenylcarboxamide
  参考文献：
  名称：

  Mazindol Analogues as Potential Inhibitors of the Cocaine Binding Site at the Dopamine Transporter

  摘要：

  A series of mazindol. (2) and homomazindol (3) analogues with a variety of electron-donating and electron-withdrawing groups in the pendant aryl group and the benzo ring C, as well as H, methoxy, and alkyl groups replacing the hydroxyl group were synthesized, and their binding affinities at the dopamine transporter (DAT) on rat or guinea pig striatal. membranes were determined. Several active analogues were also evaluated for their ability to block uptake of DA, 5-HT, and NE and inhibit binding of [I-125] RTI-55 at HEK-hDAT, HEK-hSERT, and HEK-hNET cells. Mazindane (26) was found to be a pro-drug, oxidizing (5-H --> 5-OH) to mazindol on rat striatal membranes and HEk-hDAT cells. The 4',7,8-trichloro analogue (38) of mazindol was the I most potent and selective ligand. for HEK-hDAT cells (DAT K-i = 1.1 nM; SERT/DAT 1283 and NET/DAT = 38). Experimental results strongly favor the cyclic or ol tautomers of 2 and 3 to bind more, tightly at the DAT than the corresponding keto tautomers.

  DOI：

  10.1021/jm010302r

文献信息

• 8-Aryl-1,2,3,4-tetrahydroisoquinoline and derivatives thereof
  申请人：G. D. Searle & Co.

  公开号：US04220778A1

  公开（公告）日：1980-09-02

  8-Aryl-1,2,3,4-tetrahydroisoquinoline and derivatives thereof having the formula ##STR1## and the non-toxic pharmacologically acceptable acid addition salts thereof; wherein R is hydrogen, benzyl, or an alkyl radical of 1 to 7 carbon atoms; R.sup.1 is hydrogen or an alkyl radical of 1 to 7 carbon atoms; R.sup.2 in each occurrence is hydrogen, an alkyl radical of 1 to 7 carbon atoms or alkoxy radical of 1 to 7 carbon atoms, alike or different; Ar is phenyl optionally substituted with one or more halogen, an alkyl radical of 1 to 7 carbon atoms, or alkoxy radical of 1 to 7 carbon atoms; and n is positive integer less than 4, are disclosed. These compounds are useful because of their anti-arrhythmic, antimicrobial and central nervous system activity.

  公开了具有以下式子的8-芳基-1,2,3,4-四氢异喹啉及其衍生物##STR1##和其无毒药理学上可接受的酸加合物盐; 其中R为氢、苄基或1至7个碳原子的烷基基团; R.sup.1为氢或1至7个碳原子的烷基基团; R.sup.2在每次出现时为氢、1至7个碳原子的烷基基团或1至7个碳原子的烷氧基基团，相同或不同; Ar为苯基，可选地取代一个或多个卤素，1至7个碳原子的烷基基团或1至7个碳原子的烷氧基基团; n为小于4的正整数。这些化合物由于其抗心律失常、抗微生物和中枢神经系统活性而有用。
• US4220778A
  申请人：——

  公开号：US4220778A

  公开（公告）日：1980-09-02