(4-(benzyloxy)-3-chloro-5-methoxyphenyl)methanol | 536974-92-2

• 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: (4-(benzyloxy)-3-chloro-5-methoxyphenyl)methanol
• 英文别名: (4-benzyloxy-3-chloro-5-methoxyphenyl)methanol；5-chloro-O-benzylvanillol；(4-benzyloxy-3-chloro-5-methoxy-phenyl)-methanol；(3-chloro-5-methoxy-4-phenylmethoxyphenyl)methanol
• CAS: 536974-92-2
• 化学式: C₁₅H₁₅ClO₃
• mdl: MFCD03716129
• 分子量: 278.735
• InChiKey: DJWIGOZKIYYPTC-UHFFFAOYSA-N

物化性质

• 沸点：
  420.1±40.0 °C(Predicted)
• 密度：
  1.244±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  19
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.2
• 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：

  (4-(benzyloxy)-3-chloro-5-methoxyphenyl)methanol 在 二苯基磷酸 、 水 、 1,8-二氮杂双环[5.4.0]十一碳-7-烯 、 三苯基膦 作用下， 以 四氢呋喃 、 甲苯 为溶剂， 生成 4-Benzyloxy-3-chloro-5-methoxy-benzylamine
  参考文献：
  名称：

  The Taming of Capsaicin. Reversal of the Vanilloid Activity of N-Acylvanillamines by Aromatic Iodination

  摘要：

  Aromatic iodination ortho to the phenolic hydroxyl reverts the activity of the ultrapotent vanilloid agonist resiniferatoxin (RTX, 1a), generating the ultrapotent antagonist 5'-iodoRTX (1b). To better understand the role of iodine in this remarkable switch of activity, a systematic investigation on the halogenation of vanillamides, a class of compounds structurally simpler than resiniferonoids, was carried out. The results showed that (a) the antagonistic activity depends on the site of halogenation and is maximal at C-6', (b) iodine is more efficient than chlorine and bromine at reverting the agonistic activity, and (c) iodine-carbon exchange decreases antagonist activity. Iodine-induced reversal of vanilloid activity was also observed in vanillamides more powerful than capsaicin, but a poor correlation was found between agonistic and antagonistic potencies, suggesting that differences exist in the way vanillamides and their 6'-iodo derivatives bind to TRPV1".

  DOI：

  10.1021/jm050139q
• 作为产物：
  描述：

  5-氯香草酸 在 lithium aluminium tetrahydride 、 potassium carbonate 作用下， 以 四氢呋喃 、 N,N-二甲基甲酰胺 为溶剂， 生成 (4-(benzyloxy)-3-chloro-5-methoxyphenyl)methanol
  参考文献：
  名称：

  Dual Aromatase−Steroid Sulfatase Inhibitors

  摘要：

  By introducting the steroid sulfatase inhibitory pharmacophore into aromatase inhibitor 1 (YM511), two series of single agent dual aromatase-sulfatase inhibitors (DASIs) were generated. The best DASIs in vitro (JEG-3 cells) are 5, (IC50(aromatase) = 0.82 nM; IC50(sulfatase) = 39 nM), and 14, (IC50(aromatase) = 0.77 nM; IC50(sulfatase) = 590 nM). X-ray crystallography of 5, and docking studies of selected compounds into an aromatase homology model and the steroid sulfatase crystal structure are presented. Both 5 and 14 inhibit aromatase and sulfatase in PMSG pretreated adult female Wistar rats potently 3 h after a single oral 10 mg/kg dose. Almost complete dual inhibition is observed for 5 but the levels were reduced to 85% (aromatase) and 72% (sulfatase) after 24 h. DASI 5 did not inhibit aldosterone synthesis. The development of a potent and selective DASI should allow the therapeutic potential of dual aromatase-sulfatase inhibition in hormone-dependent breast cancer to be assessed.

  DOI：

  10.1021/jm061462b

文献信息

• Compound
  申请人：——

  公开号：US20040019016A1

  公开（公告）日：2004-01-29

  There is provided a compound of Formula I 1 wherein each T is independently selected from H, hydrocarbyl, —F—R, and a bond with one of D, E, P or Q, or together with one of P and Q forms a ring; Z is a suitable atom the valency of which is m; D, E and F are each independently of each other an optional linker group, wherein when Z is nitrogen E is other than CH 2 and C═O; P, Q and R are independently of each other a ring system; and at least Q comprises a sulphamate group.

  提供了一个式I1的化合物，其中每个T分别选自H、烃基、—F—R和与D、E、P或Q中的一个之一形成键，或者与P和Q中的一个一起形成环；Z是一个适当的原子，其价数为m；D、E和F分别独立于彼此，是可选的连接基团，其中当Z是氮时，E不是CH2和C═O；P、Q和R独立于彼此，是一个环系统；至少Q包含一个磺酰胺基团。
• Synthesis of a New Carbon-11–Labeled Sulfamate Derivative as a Potential PET Tracer for Imaging of Breast Cancer Aromatase and Steroid Sulfatase Expression
  作者：Min Wang、Mingzhang Gao、Kathy D. Miller、Qi-Huang Zheng

  DOI：10.1080/00397911003797825

  日期：2011.3.28

  Abstract A carbon-11-labeled sulfamate derivative was designed and synthesized as a new potential positron-emission-tomography dual aromatase–steroid sulfatase inhibitor radiotracer for imaging of aromatase and steroid sulfatase expression in breast cancer. The target tracer 2-chloro-4-(((4-cyanophenyl)(4H-1,2,4-triazol-4-yl)amino)methyl)-6-[11C]methoxyphenyl sulfamate ([11C]7) was prepared from its

  摘要 设计并合成了一种碳 11 标记的氨基磺酸盐衍生物，作为一种新的潜在正电子发射断层扫描双芳香化酶-类固醇硫酸酯酶抑制剂放射性示踪剂，用于对乳腺癌中芳香化酶和类固醇硫酸酯酶的表达进行成像。目标示踪剂 2-氯-4-（（（4-氰基苯基）（4H-1,2,4-三唑-4-基）氨基）甲基）-6-[11C]甲氧基苯基氨基磺酸酯（[11C]7）是由其相应的前体 2-chloro-4-(((4-cyanophenyl)(4H-1,2,4-triazol-4-yl)amino)methyl)-6-hydroxyphenyl sulfamate (18) 与 [11C]CH3OTf 制备在碱性条件下通过 O-[11C] 甲基化并通过反相高效液相色谱法分离，基于 [11C]CO2 的放射化学产率为 40-45%，衰减校正至轰击结束。合成结束时的比活为111-185 GBq/μmol。
• [EN] 1,2,4-TRIAZOLE DERIVATIVES CONTAINING A SULPHAMATE GROUP AS AROMATASE INHIBITORS<br/>[FR] DERIVES 1,2,4-TRIAZOLE CONTENANT UN GROUPE SULFAMATE EN TANT QU'INHIBITEURS D'AROMATASE
  申请人：STERIX LTD

  公开号：WO2003045925A1

  公开（公告）日：2003-06-05

  There is provided a compound of Formula (I), wherein each T is independently selected from H, hydrocarbyl, -F-R, and a bond with one of D, E, P or Q, or together with one of P and Q forms a ring; Z is a suitable atom the valency of which is m; D, E and F are each independently of each other an optional linker group, wherein when Z is nitrogen E is other than CH2 and C=O; P, Q and R are independently of each other a ring system; and at least Q comprises a sulphamate group.

  提供了一个化合物的式子（I），其中每个T独立地选自H，烃基，-F-R和与D，E，P或Q中的一个之一形成键，或与P和Q中的一个形成环；Z是适当的原子，其价数为m；D，E和F分别独立于彼此的可选连接基团，其中当Z为氮时，E不是CH2和C=O；P，Q和R独立于彼此的环系统；并且至少Q包含一个磺酰胺基团。
• Polycyclic sulphamate compounds suitable for use as inhibitors of aromatase and/or sulphatase
  申请人：Sterix, Ltd.

  公开号：US07361677B2

  公开（公告）日：2008-04-22

  There is provided a compound of Formula I wherein each T is independently selected from H, hydrocarbyl, —F—R, and a bond with one of D, E, P or Q, or together with one of P and Q forms a ring; Z is a suitable atom the valency of which is m; D, E and F are each independently of each other an optional linker group, wherein when Z is nitrogen E is other than CH2 and C═O; P, Q and R are independently of each other a ring system; and at least Q comprises a sulphamate group.

  提供了一种化合物，其化学式为I，其中每个T独立地选自H、烃基、—F—R和与D、E、P或Q中的一个成键，或与P和Q中的一个形成环；Z是适当的原子，其价为m；D、E和F各自独立地为可选的连接基团，其中当Z为氮时，E不是CH2和C═O；P、Q和R各自独立地为一个环系统；并且至少Q包含一个磺酰胺基团。
• 1,2,4-TRIAZOLE DERIVATIVES CONTAINING A SULPHAMATE GROUP AS AROMATASE INHIBITORS
  申请人：Sterix Limited

  公开号：EP1446388B1

  公开（公告）日：2013-01-09