(3-(aminomethyl)phenyl)(diphenyl)methanol | 178977-70-3

• 分子结构分类: 有机化合物 - 苯类化合物 - 三苯基化合物
• 英文名称: (3-(aminomethyl)phenyl)(diphenyl)methanol
• 英文别名: [3-(Aminomethyl)phenyl]-diphenylmethanol
• CAS: 178977-70-3
• 化学式: C₂₀H₁₉NO
• 分子量: 289.377
• InChiKey: UALVOAMMBBYLQK-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  22
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.1
• 拓扑面积：
  46.2
• 氢给体数：
  2
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (3-(aminomethyl)phenyl)(diphenyl)methanol 在 三氟乙酸 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 7.0h， 生成 N-(3-(((2-aminoethyl)sulfanyl)(diphenyl)methyl)benzyl)acetamide
  参考文献：
  名称：

  Triphenylbutanamines: Kinesin Spindle Protein Inhibitors with in Vivo Antitumor Activity

  摘要：

  The human mitotic kinesin Eg5 represents a novel mitotic spindle target for cancer chemotherapy. We previously identified S-trityl-L-cysteine (STLC) and related analogues as selective potent inhibitors of Eg5. We herein report on the development of a series of 4,4,4-triphenylbutan-1-amine inhibitors derived from the STLC scaffold. This new generation systematically improves on potency: the most potent C-trityl analogues exhibit K-i(aPP) <= 10 nM and GI(50) approximate to 50 nM, comparable to results from the phase II clinical benchmark ispinesib. Crystallographic studies reveal that they adopt the same overall binding configuration as S-trityl analogues at an allosteric site formed by loop L5 of Eg5. Evaluation of their druglike properties reveals favorable profiles for future development and, in the clinical candidate ispinesib, moderate hERG and CYP inhibition. One triphenylbutanamine analogue and ispinesib possess very good bioavailability (51% and 45%, respectively), with the former showing in vivo antitumor growth activity in nude mice xenograft studies.

  DOI：

  10.1021/jm201195m
• 作为产物：
  描述：

  3-(hydroxy(diphenyl)methyl)benzonitrile 在 lithium aluminium tetrahydride 作用下， 以 四氢呋喃 为溶剂， 反应 22.0h， 以68%的产率得到(3-(aminomethyl)phenyl)(diphenyl)methanol
  参考文献：
  名称：

  Triphenylbutanamines: Kinesin Spindle Protein Inhibitors with in Vivo Antitumor Activity

  摘要：

  The human mitotic kinesin Eg5 represents a novel mitotic spindle target for cancer chemotherapy. We previously identified S-trityl-L-cysteine (STLC) and related analogues as selective potent inhibitors of Eg5. We herein report on the development of a series of 4,4,4-triphenylbutan-1-amine inhibitors derived from the STLC scaffold. This new generation systematically improves on potency: the most potent C-trityl analogues exhibit K-i(aPP) <= 10 nM and GI(50) approximate to 50 nM, comparable to results from the phase II clinical benchmark ispinesib. Crystallographic studies reveal that they adopt the same overall binding configuration as S-trityl analogues at an allosteric site formed by loop L5 of Eg5. Evaluation of their druglike properties reveals favorable profiles for future development and, in the clinical candidate ispinesib, moderate hERG and CYP inhibition. One triphenylbutanamine analogue and ispinesib possess very good bioavailability (51% and 45%, respectively), with the former showing in vivo antitumor growth activity in nude mice xenograft studies.

  DOI：

  10.1021/jm201195m

文献信息

• The phototrityl group. Photocrosslinking of oligonucleotides to BSA
  作者：A Bidaine、C Berens、E Sonveaux

  DOI：10.1016/0960-894x(96)00191-6

  日期：1996.5

  A photoactivable trityl cap was used to immobilize an oligonucleotide on BSA (bovine serum albumin). The conjugate was able to hybridize with a complementary sequence. (C) 1996 Elsevier Science Ltd
• Trityl derivatives for enhancing mass spectrometry
  申请人：SHCHEPINOV Mikhail Sergeevich

  公开号：US20080248584A1

  公开（公告）日：2008-10-09

  Compounds of formula (IIa): are provided where: X is a group capable of being cleaved from the α-carbon atom to form an ion of formula (I′) C is a carbon atom bearing a single positive charge or a single negative charge; The invention further provides compounds of formula (IIb): where: X is a counter-ion to C . The compounds of formula (IIa) and (IIb) may form ions of formula (I′) by either cleaving the C—X bond between X and the α-carbon atoms in the case of the compounds of formula (IIa) or dissociating X in the case of compounds of formula (IIb).
• Triphenylbutanamines: Kinesin Spindle Protein Inhibitors with in Vivo Antitumor Activity
  作者：Fang Wang、James A. D. Good、Oliver Rath、Hung Yi Kristal Kaan、Oliver B. Sutcliffe、Simon P. Mackay、Frank Kozielski

  DOI：10.1021/jm201195m

  日期：2012.2.23

  The human mitotic kinesin Eg5 represents a novel mitotic spindle target for cancer chemotherapy. We previously identified S-trityl-L-cysteine (STLC) and related analogues as selective potent inhibitors of Eg5. We herein report on the development of a series of 4,4,4-triphenylbutan-1-amine inhibitors derived from the STLC scaffold. This new generation systematically improves on potency: the most potent C-trityl analogues exhibit K-i(aPP) <= 10 nM and GI(50) approximate to 50 nM, comparable to results from the phase II clinical benchmark ispinesib. Crystallographic studies reveal that they adopt the same overall binding configuration as S-trityl analogues at an allosteric site formed by loop L5 of Eg5. Evaluation of their druglike properties reveals favorable profiles for future development and, in the clinical candidate ispinesib, moderate hERG and CYP inhibition. One triphenylbutanamine analogue and ispinesib possess very good bioavailability (51% and 45%, respectively), with the former showing in vivo antitumor growth activity in nude mice xenograft studies.