(2-fluoro-3,4-dimethoxyphenyl)methanol | 96994-71-7

• 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: (2-fluoro-3,4-dimethoxyphenyl)methanol
• 英文别名: 2-fluoro-3,4-dimethoxybenzyl alcohol
• CAS: 96994-71-7
• 化学式: C₉H₁₁FO₃
• 分子量: 186.183
• InChiKey: KENAPLUXUWNTDX-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.1
• 重原子数：
  13
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  38.7
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (2-fluoro-3,4-dimethoxyphenyl)methanol 在 盐酸 作用下， 以 甲苯 为溶剂， 反应 0.67h， 以81%的产率得到2-氟-3,4-二甲氧基苄氯
  参考文献：
  名称：

  Ladd, David L.; Gaitanopoulos, Dimitri; Weinstock, Joseph, Synthetic Communications, 1985, vol. 15, p. 61 - 70

  摘要：

  DOI：
• 作为产物：
  描述：

  2-氟-3,4-二甲氧基苯甲醛 在 sodium tetrahydroborate 作用下， 以 甲醇 为溶剂， 反应 0.5h， 以90%的产率得到(2-fluoro-3,4-dimethoxyphenyl)methanol
  参考文献：
  名称：

  Ring-truncated deguelin derivatives as potent Hypoxia Inducible Factor-1α (HIF-1α) inhibitors

  摘要：

  A series of fluorophenyl and pyridine analogues of 1 and 2 were synthesized as ring-truncated deguelin surrogates and evaluated for their HIF-1 alpha inhibition. Their structure-activity relationship was systematically investigated based on the variation of the linker B-region moiety. Among the inhibitors, compound 25 exhibited potent HIF-1 alpha inhibition in a dose-dependent manner and significant antitumor activity in H1299 with less toxicity than deguelin. It also inhibited in vitro hypoxia-mediated angiogenic processes in HRMECs. The docking study indicates that 25 occupied the C-terminal ATP-binding pocket of HSP90 in a similar mode as 1, which implies that the anticancer and antiangiogenic activities of 25 are derived from HIF-1 alpha destabilization by binding to the C-terminal ATP-binding site of hHSP90. (C) 2015 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2015.09.033

文献信息

• Catechol derivatives
  申请人：Hoffmann-La Roche Inc.

  公开号：US05236952A1

  公开（公告）日：1993-08-17

  Catechol derivatives of the formula ##STR1## wherein Ra, Rb and Rc have the significance given herein, the ester and ether derivatives thereof which are hydrolyzable under physiological conditions and the pharmaceutically acceptable salts thereof are described and possess valuable pharmacological properties. In particular, they inhibit the enzyme catechol-O-methyltransferase (COMT), a soluble, magnesium-dependent enzyme which catalyses the transference of the methyl group of S-adensoylmethionine to a catechol substrate, whereby the corresponding methyl ethers are formed. Suitable substrates which can be O-methylated by COMT and which can thus be deactivated are, for example, extraneuornal catecholamines and exogeneously-administered therapeutically active substances having a catechol structure. Formula Ia above embraces not only compounds which form part of the invention, but also known compounds; the compounds which form part of the invention can be prepared according to known methods.

  公式##STR1##中的儿茶酚衍生物，其中Ra、Rb和Rc具有本文中给出的含义，以及在生理条件下可水解的酯和醚衍生物及其药学上可接受的盐已被描述，并具有有价值的药理特性。特别是，它们抑制儿茶酚-O-甲基转移酶(COMT)这种可溶性、依赖镁的酶，该酶催化S-腺苷甲硫氨酸的甲基基团转移到儿茶酚底物上，从而形成相应的甲基醚。可被COMT进行O-甲基化并因此被失活的适当底物包括，例如，外源性儿茶酚胺和具有儿茶酚结构的外源性给药的治疗活性物质。上述公式Ia不仅包括发明的一部分化合物，还包括已知的化合物；构成发明一部分的化合物可以按照已知方法制备。
• Phenylethylamines, process for their preparation and compositions containing them
  申请人：FISONS plc

  公开号：EP0142283A2

  公开（公告）日：1985-05-22

  There are described compounds ofiformula I, in which R, represents OH, NR11R12, CH2R12 or fluorine, R2, R3, R11, R12 and R2, have various meanings as defined herein for example R2 and R3 may represent hydrogen, halogen, alkyl C1 to 6 or nitro; W represents a single bond, a disubstituted benzene or a 1,4-cyclohexanediyl group, X represents NH, 0, S, SO2, CO, CH2, CONH or-COO; Y, amongst other meanings defined herein, represents (CH2)q, CO, CS and SO2, Z represents a single bond, NR19, CH2, O, CO, S or SO2, in which R10 represents hydrogen or alkyl C1 to 6, n and m each independently represent an integer from 1 to 4 inclusive, q represents an integer from 1 to 3 inclusive, p represents 0 or an integer from 1 to 3 inclusive, R10 represents hydrogen or chlorine, R20, amongst other meanings defined herein may represent hydrogen, with four provises as defined herein, and pharmaceutically acceptable derivatives thereof. There are also described the use of the compounds of formula 1 as pharmaceuticals, methods for making the compounds and pharmaceutical, e.g. cardiac, compositions containing the compounds.

  描述了芴甲氧羰基化合物 I、 其中 R 代表 OH、NR11R12、CH2R12 或氟、 R2、R3、R11、R12 和 R2 具有本文所定义的各种含义，例如 R2 和 R3 可代表氢、卤素、C1-6 烷基或硝基； W 代表单键、二取代苯或 1,4-环己二基、 X 代表 NH、0、S、SO2、CO、CH2、CONH 或-COO； 除本文定义的其他含义外，Y 代表 (CH2)q、CO、CS 和 SO2、 Z 代表单键、NR19、CH2、O、CO、S 或 SO2，其中 R10 代表氢或 C1-6 烷基、 n 和 m 各自独立地代表 1 至 4（含 4）的整数、 q 代表 1 至 3（包括 3）的整数、 p 代表 0 或 1 至 3（包括 3）的整数、 R10 代表氢或氯、 R20，除本文定义的其他含义外，可代表氢，以及本文定义的四个前缀，及其药学上可接受的衍生物。 此外，还描述了式 1 化合物作为药物的用途、制造该化合物的方法以及含有该化合物的药物组合物，如心脏病组合物。
• Ladd, David L.; Gaitanopoulos, Dimitri; Weinstock, Joseph, Synthetic Communications, 1985, vol. 15, p. 61 - 70
  作者：Ladd, David L.、Gaitanopoulos, Dimitri、Weinstock, Joseph

  DOI：——

  日期：——
• 3,5-Disubstituierte Pyrocatecholderivate
  申请人：F. HOFFMANN-LA ROCHE AG

  公开号：EP0237929B1

  公开（公告）日：1993-06-02
• US4720586A
  申请人：——

  公开号：US4720586A

  公开（公告）日：1988-01-19