(2,5-dimethoxybenzyl)triphenylphosphonium bromide

• 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: (2,5-dimethoxybenzyl)triphenylphosphonium bromide
• 英文别名: 2,5-dimethoxybenzyltriphenylphosphine bromide；2,5-dimethoxybenzyl triphenylphosphonium bromide；2,5-dimethoxybenzyl-triphenylphosphonium bromide；(2,5-Dimethoxybenzyl)(triphenyl)phosphonium bromide；(2,5-dimethoxyphenyl)methyl-triphenylphosphanium;bromide
• 化学式: Br*C₂₇H₂₆O₂P
• 分子量: 493.38
• InChiKey: FVUDWHPJVYTKDT-UHFFFAOYSA-M

计算性质

• 辛醇/水分配系数(LogP)：
  2.2
• 重原子数：
  31
• 可旋转键数：
  7
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.11
• 拓扑面积：
  18.5
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (2,5-dimethoxybenzyl)triphenylphosphonium bromide 在 palladium on activated charcoal 正丁基锂 、 氢气 、 二异丙胺 作用下， 以 乙酸乙酯 为溶剂， -70.0~25.0 ℃ 、98.06 kPa 条件下， 反应 34.0h， 生成 SDZ LAP 977
  参考文献：
  名称：

  Novel Antiproliferative Agents Derived from Lavendustin A

  摘要：

  The active partial structure of the potent tyrosine kinase inhibitor lavendustin A was derivatized in the search for novel agents against cellular proliferation. The antiproliferative potential of the new derivatives was determined using the human keratinocyte cell line HaCaT as the primary test system. Whereas the lavendustin A partial structure is ineffective in inhibiting cell proliferation, esterification of its carboxylic acid function leads to measurable antiproliferative activity. Additional O-methylation of the 2,5-dihydroxyphenyl moiety yields activity in the micromolar range. Further substantial increases in activity are achieved by replacing the nitrogen with oxygen and carbon within the 2,5-dimethoxyphenyl series (but not within the 2,5-dihydroxyphenyl analogs) leading to 5-[2-(2,5-dimethoxyphenyl)ethyl]-2-hydroxybenzoic acid methyl ester (13) as the most potent analog identified to date. These increases in antiproliferative activity are paralleled, however, by the disappearance of activity against the epidermal growth factor receptor-associated tyrosine kinase, suggesting another mechanism of action.

  DOI：

  10.1021/jm00050a005
• 作为产物：
  描述：

  对二甲氧基苯甲醇 在 N-溴代丁二酰亚胺(NBS) 、 三苯基膦 作用下， 以 四氢呋喃 、 氯仿 为溶剂， 反应 1.5h， 生成 (2,5-dimethoxybenzyl)triphenylphosphonium bromide
  参考文献：
  名称：

  吲哚和吲唑基二苯乙烯的设计、合成和细胞毒活性

  摘要：

  为了开发天然存在的二苯乙烯支架衍生的新型高效抗癌剂，根据分子杂交策略设计并通过 Witting 反应合成了总共 24 种吲唑和吲唑类二苯乙烯类化合物，包括 17 种新化合物。针对人类肿瘤细胞系（K562 细胞和 MDA-MB-231 细胞）的细胞毒性筛选结果表明，基于吲哚和吲唑的二苯乙烯类化合物对于开发抗癌剂具有重要意义，因为八种衍生物具有很强的抗增殖活性，IC 为50值小于 10 μM，并且这些合成衍生物对 K562 细胞表现出比 MDA-MB-231 细胞更高的细胞毒性。特别是，基于吲哚的二苯乙烯基哌啶对 K562 和 MDA-MB-231 细胞表现出最有效的细胞毒性，IC 50 值分别为2.4 μM 和 2.18 μM，并且对人正常 L-02 细胞具有显着的选择性。总之，结果表明基于吲哚和吲唑的二苯乙烯是有前途的抗癌支架，值得进一步研究。

  DOI：

  10.1002/cbdv.202300368

文献信息

• Synthesis of three carbon atom bridged 2,4-diaminopyrrolo[2,3-<i>d</i>]-pyrimidines as nonclassical dihydrofolate reductase inhibitors
  作者：Aleem Gangjee、Zhengqu Ye、Sherry F. Queener

  DOI：10.1002/jhet.5570420614

  日期：2005.9

  3-d]-pyrimidines 1a-g. Preliminary biological results indicated that these compounds showed moderate inhibitory activities against dihydrofolate reductases from Pneumocystis carinii, Toxoplasma gondii, Mycobacterium avium and rat liver with IC50 values in the 0.66 μM - 70.1 μM range and some compounds had marginal selectivity for T. gondii dihydrofolate reductase.

  合成了一系列七个非经典的三个碳原子桥接的2,4-二氨基-5-取代的吡咯并[2,3- d ]-吡啶1a-g作为二氢叶酸还原酶的潜在抑制剂。二醇7a-g的选择性氧化得到α-羟基酮8a-g。随后与丙二腈缩合，得到必需的2-氨基-3-氰基-4-取代的呋喃前体9a-g。一步在回流的乙醇中与胍进行环缩合，得到三个碳原子桥接的2,4-二氨基-5-取代的吡咯并[2,3- d ]-嘧啶1a-g。初步生物学结果表明，这些化合物对卡氏肺孢子虫，弓形虫，鸟形分枝杆菌和大鼠肝脏中的二氢叶酸还原酶表现出中等抑制作用，IC 50值在0.66μM-70.1μM范围内，并且某些化合物对弓形虫二氢叶酸还原酶的选择性很小。。
• Trisubstituted phenyl derivatives
  申请人：Novartis AG

  公开号：US05990116A1

  公开（公告）日：1999-11-23

  The invention concerns compounds of formula I ##STR1## wherein the substituents have various meanings, and their use in the prevention or treatment of inflammatory and proliferative skin diseases and cancer.

  这项发明涉及到式I的化合物，其中取代基具有不同的含义，并且它们在预防或治疗炎症性和增生性皮肤疾病以及癌症方面的应用。
• Hydroquinone–pyrrole dyads with varied linkers
  作者：Hao Huang、Christoffer Karlsson、Maria Strømme、Martin Sjödin、Adolf Gogoll

  DOI：10.3762/bjoc.12.10

  日期：——

  A series of pyrroles functionalized in the 3-position with p-dimethoxybenzene via various linkers (CH₂, CH₂CH₂, CH=CH, C≡C) has been synthesized. Their electronic properties have been deduced from ¹H NMR, ¹³C NMR, and UV–vis spectra to detect possible interactions between the two aromatic subunits. The extent of conjugation between the subunits is largely controlled by the nature of the linker, with the largest conjugation found with the trans-ethene linker and the weakest with the aliphatic linkers. DFT calculations revealed substantial changes in the HOMO–LUMO gap that correlated with the extent of conjugation found experimentally. The results of this work are expected to open up for use of the investigated compounds as components of redox-active materials in sustainable, organic electrical energy storage devices.

  一系列在3位被p-二甲氧基苯基通过不同的连接基（CH2，CH2CH2，CH=CH，C≡C）官能化的吡咯已被合成。通过1H NMR，13C NMR和UV-vis光谱推断它们的电子性质，以检测两个芳香基团之间可能的相互作用。基团之间的共轭程度在很大程度上由连接基的性质控制，其中使用trans-乙烯基连接基具有最大的共轭，而脂肪族连接基则最弱。DFT计算揭示了与实验发现的共轭程度相关的HOMO-LUMO间隙的显着变化。这项工作的结果预计将为可持续的有机电能存储器材料的组分使用这些研究化合物开辟道路。
• Bis(phenyl)ethane derivatives
  申请人：Sandoz Ltd.

  公开号：US05488135A1

  公开（公告）日：1996-01-30

  The invention concerns the compounds of formula I ##STR1## wherein the substituents have various significances, in free form and, where such forms exist, in salt form. The compounds have potent antihyperproliferative/antiinflammatory and anticancer activity.

  本发明涉及公式I的化合物 ##STR1## 其中取代基具有各种意义，包括自由形式和盐形式（如果存在这些形式）。这些化合物具有强效的抗高增殖/抗炎和抗癌活性。
• 2,10-Disubstituted dibenzo[b,d]pyrans and benzo[c]quinolines
  申请人：Pfizer Inc.

  公开号：US04206225A1

  公开（公告）日：1980-06-03

  A compound of the formula ##STR1## wherein Q is CH.sub.2, C.dbd.O, CHOH or CHCH.sub.2 OH; M is O or NR.sub.6 ; where R.sub.6 is hydrogen, or certain alkyl, aralkyl, acyl or carboalkoxy substituted alkyl groups; R.sub.1 is hydrogen, or certain alkanoyl or amino substituted alkanoyl groups; R.sub.4 and R.sub.5 are each hydrogen or alkyl having from 1 to 4 carbon atoms; Z is alkylene having from 1 to 9 carbon atoms or --(alk.sub.1)--X--(alk.sub.2).sub.n -- where (alk.sub.1) and (alk.sub.2) are certain alkylene groups and X is O, S, SO or SO.sub.2 ; W is a methyl, phenyl, substituted phenyl, pyridyl, piperidyl, cycloalkyl or substituted cycloalkyl group and the pharmaceutically acceptable and addition salts of said compounds having a basic nitrogen atoms. Said compounds are useful as analgesics and as intermediates therefore.

  一种化合物的公式为##STR1##其中Q为CH.sub.2，C.dbd.O，CHOH或CHCH.sub.2OH; M为O或NR.sub.6;其中R.sub.6为氢，或某些烷基，芳基烷基，酰基或羧基烷氧基取代烷基基团; R.sub.1为氢，或某些烷酰基或氨基取代的烷酰基基团; R.sub.4和R.sub.5分别为氢或具有1至4个碳原子的烷基; Z为具有1至9个碳原子的烷基或--(alk.sub.1)--X--(alk.sub.2).sub.n--其中(alk.sub.1)和(alk.sub.2)是某些烷基基团，X为O，S，SO或SO.sub.2; W为甲基，苯基，取代苯基，吡啶基，哌啶基，环烷基或取代环烷基基团和具有含有碱性氮原子的药学上可接受的和加成盐。这些化合物可用作镇痛剂和其中间体。