(3-((4-methoxybenzyloxy)methyl)phenyl)methanol | 1182869-77-7

• 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: (3-((4-methoxybenzyloxy)methyl)phenyl)methanol
• 英文别名: [3-[(4-Methoxyphenyl)methoxymethyl]phenyl]methanol；[3-[(4-methoxyphenyl)methoxymethyl]phenyl]methanol
• CAS: 1182869-77-7
• 化学式: C₁₆H₁₈O₃
• 分子量: 258.317
• InChiKey: WHXWTSNLEBWNHR-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.2
• 重原子数：
  19
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  38.7
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (3-((4-methoxybenzyloxy)methyl)phenyl)methanol 在 咪唑 、 4-二甲氨基吡啶 、 草酰氯 、 四氯化钛 、 戴斯-马丁氧化剂 、 二甲基亚砜 、 2,3-二氯-5,6-二氰基-1,4-苯醌 、 锌 作用下， 以 四氢呋喃 、 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 27.5h， 生成 3-(1,1-bis(4-(tert-butyldimethylsilyloxy)phenyl)but-1-en-2-yl)benzaldehyde
  参考文献：
  名称：

  ペプチド

  摘要：

  提供在体内显示足够的蛋白酶体抑制活性的化合物。通过将与19S调节因子识别相关的含有4个至10个氨基酸残基的肽与式（A）所示的他莫西芬化合物结合而成的化合物。（R1和R2各自独立地是H或C1-6烷基，或者R1和R2相互结合形成饱和的5-8元环；R8是羧基或氨甲基）【选择图】无

  公开号：

  JP2016222659A
• 作为产物：
  描述：

  1,3-苯二甲醇 、 4-甲氧基氯苄 在 四丁基碘化铵 、 sodium hydride 作用下， 以 四氢呋喃 为溶剂， 反应 4.0h， 以33%的产率得到(3-((4-methoxybenzyloxy)methyl)phenyl)methanol
  参考文献：
  名称：

  ペプチド

  摘要：

  提供在体内显示足够的蛋白酶体抑制活性的化合物。通过将与19S调节因子识别相关的含有4个至10个氨基酸残基的肽与式（A）所示的他莫西芬化合物结合而成的化合物。（R1和R2各自独立地是H或C1-6烷基，或者R1和R2相互结合形成饱和的5-8元环；R8是羧基或氨甲基）【选择图】无

  公开号：

  JP2016222659A

文献信息

• [EN] HEMI-PHORBOXAZOLE A DERIVATIVES AND METHODS OF THEIR USE<br/>[FR] DÉRIVÉS DE L'HÉMI-PHORBOXAZOLE A ET LEURS PROCÉDÉS D'UTILISATION
  申请人：UNIV PENNSYLVANIA

  公开号：WO2011011665A1

  公开（公告）日：2011-01-27

  The present invention is directed to hemi phorboxazole A: and its stereoisomers, as well as derivatives of hemi phorboxazole A of formula I: wherein ring A is aryl or a 5- or 6-membered heteroaryl optionally substituted with one or more of halogen, -OH, or -C1-6alkyl; and R is-CN, a 5- or 6-membered heteroaryl, or halogen; and the pharmaceutically acceptable salt forms thereof, in addition to methods of using these compounds.

  本发明涉及半磷酸酯A及其立体异构体，以及公式I中的半磷酸酯A的衍生物：其中环A是芳基或5-或6-成员杂芳基，可以选择地被一个或多个卤素，-OH或-C1-6烷基取代；R是-CN，5-或6-成员杂芳基，或卤素；以及其药用盐形式，以及使用这些化合物的方法。
• Hemi-Phorboxazole A: Structure Confirmation, Analogue Design and Biological Evaluation
  作者：Amos B. Smith、Zhuqing Liu、Anne-Marie L. Hogan、Doralyn S. Dalisay、Tadeusz F. Molinski

  DOI：10.1021/ol9014317

  日期：2009.8.20

  A synthesis providing totally synthetic (+)-hemi-phorboxazole A (1), proceeding in two steps (85% yield) from known vinyl iodide precursor (+)-2, has been achieved in conjunction with the design, synthesis, and biological evaluation of two hemi-phorboxazole analogues [(+)-3 and (-)-4] featuring ring replacements inscribed within the macrolide. Although hemi-phorboxazole A (1) displayed no activity when tested against Candida albicans and two human cancer cell lines, analogue (-)-4 exhibited significant tumor cell growth inhibitory activity in the nanomolar range against HCT-116 (colon) and SK-BR-3 (breast), while (+)-3 displayed promising antifungal activity against C. albicans.
• Ridaifen-F conjugated with cell-penetrating peptides inhibits intracellular proteasome activities and induces drug-resistant cell death
  作者：Makoto Tanaka、Yunhao Zhu、Masafumi Shionyu、Nozomi Ota、Natsumi Shibata、Chihiro Watanabe、Akihito Mizusawa、Ryuzo Sasaki、Tamio Mizukami、Isamu Shiina、Makoto Hasegawa

  DOI：10.1016/j.ejmech.2018.01.045

  日期：2018.2

  Ridaifen-F (RID-F) potently inhibits proteolytic activities of the 205 proteasome but poorly inhibits those of the 26S proteasome. Here, we report preparation of several conjugates in which various peptides are connected to RID-F. Conjugates with peptides consisting of seven amino acid residues significantly inhibited the 26S proteasome. Particularly, R ID-F conjugated to an octaarginine peptide (R-8, a so-called cell-penetrating peptide) inhibited intracellular proteasome activities and induced cell death in drug resistant KMS-11 myeloma cells. RID-F conjugated to hydrophobic peptides also inhibited the 26S proteasome but failed to induce cell death, suggesting poor penetration into cells. We infer that the R-8 peptide has dual functions: (1) rapid penetration of conjugates into the cell increases intracellular drug concentrations sufficient for exhibition of its effect, and (2) recognition of the conjugates by the 26S proteasome stimulates drug entry into the catalytic chamber. In the presence of ATP gamma S, RID-F conjugates containing R-8 inhibited the 26S proteasome more potently than in the presence of ATP, suggesting efficient entry of drugs into the catalytic chamber in a similar fashion to the substrate. Taken together with docking simulations of RID-F conjugate interactions with proteasome active sites, the second function of R-8 peptide is plausible. Thus, the conjugation of nonpeptidic proteasome inhibitors to a cell penetrating peptide could represent a viable strategy for overcoming the drug-resistance of tumor cells. (C) 2018 Elsevier Masson SAS. All rights reserved.
• HEMI-PHORBOXAZOLE A DERIVATIVES AND METHODS OF THEIR USE
  申请人：Smith, III Amos B.

  公开号：US20130030027A1

  公开（公告）日：2013-01-31

  The present invention is directed to hemi phorboxazole A: and its stereoisomers, as well as derivatives of hemi phorboxazole A of formula I: wherein ring A is aryl or a 5- or 6-membered heteroaryl optionally substituted with one or more of halogen, —OH, or —C 1-6 alkyl; and R is —CN, a 5- or 6-membered heteroaryl, or halogen; and the pharmaceutically acceptable salt forms thereof, in addition to methods of using these compounds.
• US8957097B2
  申请人：——

  公开号：US8957097B2

  公开（公告）日：2015-02-17