6-benzhydryloxy-dihydropyran-3-one | 891783-72-5

• 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: 6-benzhydryloxy-dihydropyran-3-one
• 英文别名: 6-Benzhydryloxyoxan-3-one；6-benzhydryloxyoxan-3-one
• CAS: 891783-72-5
• 化学式: C₁₈H₁₈O₃
• 分子量: 282.339
• InChiKey: LFPSTYJHDWKTHE-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  21
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.28
• 拓扑面积：
  35.5
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  6-benzhydryloxy-dihydropyran-3-one 、 对氟苄胺 在 溶剂黄146 、 sodium cyanoborohydride 作用下， 以 二氯甲烷 、 甲醇 为溶剂， 反应 6.0h， 以80%的产率得到cis-(6-benzhydryloxy-tetrahydro-pyran-3-yl)-(4-fluorobenzyl)-amine
  参考文献：
  名称：

  Design, synthesis, and preliminary SAR study of 3- and 6-side-chain-extended tetrahydro-pyran analogues of cis- and trans-(6-benzhydryl-tetrahydropyran-3-yl)-benzylamine

  摘要：

  In our effort to further understand interaction of novel pyran derivatives with monoamine transporters, we have designed, synthesized, and biologically characterized side-chain-extended derivatives of our earlier developed cis- and trans-(6-benz-hydryl-tetrahydro-pyran -3-yl)-benzylamine derivatives. Both 3- and 6-position extensions were explored. All synthesized derivatives were tested for their affinities for the dopamine transporter (DAT), serotonin transporter (SERT), and norepinephrine transporter (NET) in the brain by measuring their potency in inhibiting the uptake of [H-3]DA, [H-3]5-HT, and [H-3]NE, respectively. Compounds were also tested for their binding affinity at the DAT by their ability to inhibit binding of [H-3]WIN 35, 428. The results indicated that extension at the 3-position resulted in loss of activity compared to the original compound 1. Oil the other hand, extension at the 6-position resulted in improvement of activity in the compound cis-12 by 2-fold over the parent compound 1 indicating favorable interaction. In addition, two glycoside derivatives were designed, synthesized, and biologically characterized. The glycosidic trans-isomer 24 exhibited highest potency for the NET in the current series of compounds. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2006.01.051
• 作为产物：
  描述：

  6-乙酰氧基-2H-吡喃-3(6H)-酮 在 四氯化锡 、 L-Selectride 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 5.33h， 生成 6-benzhydryloxy-dihydropyran-3-one
  参考文献：
  名称：

  Design, synthesis, and preliminary SAR study of 3- and 6-side-chain-extended tetrahydro-pyran analogues of cis- and trans-(6-benzhydryl-tetrahydropyran-3-yl)-benzylamine

  摘要：

  In our effort to further understand interaction of novel pyran derivatives with monoamine transporters, we have designed, synthesized, and biologically characterized side-chain-extended derivatives of our earlier developed cis- and trans-(6-benz-hydryl-tetrahydro-pyran -3-yl)-benzylamine derivatives. Both 3- and 6-position extensions were explored. All synthesized derivatives were tested for their affinities for the dopamine transporter (DAT), serotonin transporter (SERT), and norepinephrine transporter (NET) in the brain by measuring their potency in inhibiting the uptake of [H-3]DA, [H-3]5-HT, and [H-3]NE, respectively. Compounds were also tested for their binding affinity at the DAT by their ability to inhibit binding of [H-3]WIN 35, 428. The results indicated that extension at the 3-position resulted in loss of activity compared to the original compound 1. Oil the other hand, extension at the 6-position resulted in improvement of activity in the compound cis-12 by 2-fold over the parent compound 1 indicating favorable interaction. In addition, two glycoside derivatives were designed, synthesized, and biologically characterized. The glycosidic trans-isomer 24 exhibited highest potency for the NET in the current series of compounds. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2006.01.051

文献信息

• TRI-SUBSTITUTED 2-BENZHYDRYL-5-BENZLAMINO-TETRAHYDRO-PYRAN-4-OL AND 6-BENZHYDRYL-4-BENZYLAMINO-TETRAHYDRO-PYRAN-3-OL ANALOGUES, AND NOVEL 3,6-DISUBSTITUTED PYRAN DERIVATIVES
  申请人：WAYNE STATE UNIVERSITY

  公开号：EP1976381B1

  公开（公告）日：2013-07-24
• Design, synthesis, and preliminary SAR study of 3- and 6-side-chain-extended tetrahydro-pyran analogues of cis- and trans-(6-benzhydryl-tetrahydropyran-3-yl)-benzylamine
  作者：Shijun Zhang、Juan Zhen、Maarten E.A. Reith、Aloke K. Dutta

  DOI：10.1016/j.bmc.2006.01.051

  日期：2006.6

  In our effort to further understand interaction of novel pyran derivatives with monoamine transporters, we have designed, synthesized, and biologically characterized side-chain-extended derivatives of our earlier developed cis- and trans-(6-benz-hydryl-tetrahydro-pyran -3-yl)-benzylamine derivatives. Both 3- and 6-position extensions were explored. All synthesized derivatives were tested for their affinities for the dopamine transporter (DAT), serotonin transporter (SERT), and norepinephrine transporter (NET) in the brain by measuring their potency in inhibiting the uptake of [H-3]DA, [H-3]5-HT, and [H-3]NE, respectively. Compounds were also tested for their binding affinity at the DAT by their ability to inhibit binding of [H-3]WIN 35, 428. The results indicated that extension at the 3-position resulted in loss of activity compared to the original compound 1. Oil the other hand, extension at the 6-position resulted in improvement of activity in the compound cis-12 by 2-fold over the parent compound 1 indicating favorable interaction. In addition, two glycoside derivatives were designed, synthesized, and biologically characterized. The glycosidic trans-isomer 24 exhibited highest potency for the NET in the current series of compounds. (c) 2006 Elsevier Ltd. All rights reserved.