2,4-Dibenzyloxybenzonitrile | 170279-11-5

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: 2,4-Dibenzyloxybenzonitrile
• 英文别名: 2,4-bis(phenylmethoxy)benzonitrile
• CAS: 170279-11-5
• 化学式: C₂₁H₁₇NO₂
• 分子量: 315.371
• InChiKey: YNRZTBWNLPFPOL-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.6
• 重原子数：
  24
• 可旋转键数：
  6
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.1
• 拓扑面积：
  42.2
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  2,4-Dibenzyloxybenzonitrile 在 双氧水 、 potassium carbonate 作用下， 以 水 、 二甲基亚砜 为溶剂， 反应 0.5h， 生成 2,4-Dibenzyloxybenzamide
  参考文献：
  名称：

  Identification, synthesis and pharmacological evaluation of novel anti-EV71 agents via cyclophilin A inhibition

  摘要：

  In this work, the relationship between cyclophilin A (CypA) and EV71 prompted us to screen a series of small molecular CypA inhibitors which were previously reported by our group. Among them, compounds 1 and 2 were discovered as non-immunosuppressive anti-EV71 agents with an EC50 values of 1.07 +/- 0.17 mu M and 3.36 +/- 0.45 mu M in virus assay, respectively, which were desirably for the further study. The subsequent chemical modifications derived a novel class of molecules, among which compound 11 demonstrated the most potent anti-EV71 activity in virus assay (EC50 = 0.37 +/- 0.17 mu M), and low cytotoxicity (CC50 > 25 mu M). The following CypA enzyme inhibition studies indicated that there was not only the enzyme inhibition activity, undoubtedly important, functioning in the antiviral process, but also some unknown mechanisms worked in combination, and the further study is underway in our laboratory. Nevertheless, to the best of our knowledge, compound 11 was probably the most potent small molecular anti-EV71 agent via CypA inhibitory mechanism to date. Consequently, our study provided a new potential small molecule for curing EV71 infection. (C) 2015 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2015.11.002
• 作为产物：
  描述：

  2,4-二苄氧基苯甲醛 在 ammonium dihydrogen phosphate 、 硝基丙烷 作用下， 以 溶剂黄146 为溶剂， 反应 15.0h， 以40%的产率得到2,4-Dibenzyloxybenzonitrile
  参考文献：
  名称：

  Selective endothelin A receptor ligands. 1. Discovery and structure-activity of 2,4-disubstituted benzoic acid derivatives

  摘要：

  This paper describes the discovery of a new non-peptide endothelin A (ETA) selective ligand, 2,4-dibenzyloxybenzoic acid 3, which inhibits the binding of [I-125]ET-1 to ETA receptors with an IC50 of 9 mu M (ET-1 = endothelin-1). Optimisation of 3 resulted in compound 52 which had an IC50 of 1 mu M. One of the analogues of 3, compound 15, was examined in a functional assay and shown to antagonise ET-1-induced contraction of rat aorta. The identification of 3 was made through the application of ChemDBS-3D searching of our corporate database. The 3D query, using an aromatic ring to a carboxylic acid group separated by 10.2 +/- 1.1 Angstrom, was derived from an examination of common pharmacophoric distances found in the low energy conformations of two known ETA antagonists, the cyclic pentapeptide BQ 123 1 and myriceron caffeoyl ester 2.

  DOI：

  10.1016/s0223-5234(97)81678-9

文献信息

• Selective para-Cyanation of Alkoxy- and Benzyloxy-Substituted Benzenes with Potassium Ferricyanide Promoted by Copper(II) Nitrate and Iodine
  作者：Yunlai Ren、Mengjie Yan、Shuang Zhao、Jianji Wang、Junying Ma、Xinzhe Tian、Weiping Yin

  DOI：10.1002/adsc.201200235

  日期：2012.8.13

  A simple method was developed for selective para-cyanation of alkoxy- and benzyloxy-substituted benzenes with 0.5 equivalents of potassium ferricyanide, 0.8 equivalants of copper(II) nitrate and 0.5 equivalents of iodine in acetonitrile. Among various phenyl carbon-hydrogen bonds, those at the para-position with regard to the alkoxy or benzyloxy groups were selectively cyanated in 20% to 87% yields

  一个简单的方法，用于选择性地开发对用0.5当量的铁氰化钾，硝酸铜0.8 equivalants和在乙腈中的0.5当量的碘的烷氧基和苄氧基-取代的苯的-cyanation。在各种苯基碳氢键中，相对于烷氧基或苄氧基处于对位的那些被选择性氰化，产率为20％至87％（23个例子）。本方法使用可商购的试剂，并且可以以十克规模进行。有趣的是，在不存在铁氰化钾的情况下，甲氧基苯以32％的产率氰化，这表明一部分产品的腈基可能来自溶剂乙腈。
• Substituted phenyl compounds
  申请人：Rhone-Poulenc Rorer Limited

  公开号：US06211234B1

  公开（公告）日：2001-04-03

  Compounds of formula (I) are described wherein R1 is hydrogen, -(lower alkyl)q(CO2R6 or OH), —CN, —C(R7)═NOR8, NO2, —O(lower alkyl)R9, —C≡C—R10, —CR11═C(R12)(R13), —C(═O)CH2C(═O)CO2H, —CO(R14), alkylthio, alkylsulphinyl, alkylsulphonyl, carbamoyl, thiocarbamoyl, substituted carbamoyl, substituted thiocarbamoyl, sulphamoyl or an optionally substituted nitrogen-containing ring, m, n, o and p are independently zero or 1 and R2, R3, R4 and R5 are various groups; and physiologically acceptable salts, N-oxides and prodrugs thereof. The compounds have endothelin antagonist activity and are useful as pharmaceuticals.

  式(I)的化合物描述如下，其中R1为氢，-(较低烷基)q(CO2R6或OH)，—CN，—C(R7)HNOR8，NO2，—O(较低烷基)R9，—C≡C—R10，—CR11CH(R12)(R13)，—C(O)CH2C(O)CO2H，—CO(R14)，烷基硫醚，烷基亚砜基，烷基磺酰基，氨基甲酰基，硫代氨基甲酰基，取代的氨基甲酰基，取代的硫代氨基甲酰基，磺酰胺基或可选择取代的含氮环，m、n、o和p独立地为零或1，R2、R3、R4和R5为各种基团；以及其生理学上可接受的盐、N-氧化物和前药。这些化合物具有内皮素拮抗活性，并可用作药物。
• Synthesis of benzonitriles from substituted benzaldehyde
  申请人：Genzyme Corporation

  公开号：US20030220504A1

  公开（公告）日：2003-11-27

  There is a significant demand for organic nitriles, based on their versatility in reactions. Compounds prepared from nitriles have properties including superoxide inhibition, ferrielectric liquid crystal dopant, antipicornaviral agents, anti-inflammatory agents, anti-asthma agents, and fibringoen antagonists. The present invention discloses a facile synthesis for 2,4-dihydroxybenzonitrile, and ethers and diethers thereof, from 2,4-dihydroxybenzaldehyde or 2,4-dimethoxybenzaldehyde. The present invention also discloses a method of preparing a class of iron chelating agents related to desferrithiocin, all of which contain a thiazoline ring. In this method, 2,4-dihydroxybenzonitrile is condensed with (S)-2-methylcysteine.

  有机腈的需求很大，因为它们在反应中的多功能性。从腈制备的化合物具有包括超氧化物抑制、铁电液晶掺杂剂、抗肠病毒药物、抗炎药物、抗哮喘药物和纤维蛋白原拮抗剂在内的性质。本发明揭示了一种简便的合成2,4-二羟基苯甲腈及其醚和二醚，从2,4-二羟基苯甲醛或2,4-二甲氧基苯甲醛制备。本发明还揭示了一种制备与脱铁硫胂素相关的一类铁螯合剂的方法，所有这些剂都含有噻唑环。在这种方法中，2,4-二羟基苯甲腈与(S)-2-甲基半胱氨酸缩合。
• [EN] SYNTHESIS OF 2-ALKYLCYSTEINES, 2-(HYDROXYLATED PHENYL)-4-ALKYLTHIAZOLINE-4-CARBOXYLIC ACIDS AND DERIVATIVES THEREOF<br/>[FR] SYNTHESE DES ACIDES 2-ALKYLCYSTEINES, 2-(PHENYLE HYDROXYLE)-4-ALKYLTHIAZOLINE-4-CARBOXYLIQUES ET DE LEURS DERIVES
  申请人：GENZYME CORP

  公开号：WO2003097622A2

  公开（公告）日：2003-11-27

  The present invention provides methods of preparing 2-alkylcysteine derivatives, many of which can be performed stereoselectively. The present invention also discloses a method of preparing a class of iron chelating agents related to desferrithiocin, all of which contain a thiazoline ring. An example of these iron chelating agents are 4,5-dihydro-2-(2,4-dihydroxyphenyl)-4-alkyl-thiazole-4-carboxylic acids, such as 4,5-dihydro-2-(2,4-dihydroxyphenyl)-4-methyl-thiazole-4-carboxylic acid.

  本发明提供了制备2-烷基半胱氨酸衍生物的方法，其中许多可以进行立体选择性。本发明还披露了一种制备与去铁蒺藜菌素相关的一类铁螯合剂的方法，所有这些铁螯合剂都含有噻唑环。这些铁螯合剂的一个例子是4,5-二氢-2-(2,4-二羟基苯基)-4-烷基噻唑-4-羧酸，例如4,5-二氢-2-(2,4-二羟基苯基)-4-甲基噻唑-4-羧酸。
• Synthesis of substituted thiazoline carboxylic acids
  申请人：Genzyme Corporation

  公开号：US20040082796A1

  公开（公告）日：2004-04-29

  A useful and efficient method of preparing an alkylated thiazoline carboxylic acid, or a derivative thereof, comprises coupling a substituted aryl nitrile such as, for example, 2,4-dimethoxybenzonitrile or 4-methoxybenzonitrile, with a cysteine ester to form a substituted thiazoline carboxylic acid ester; optionally hydrolyzing the substituted thiazoline carboxylic acid ester to form a substituted thiazoline carboxylic acid; optionally, protecting the carboxyl group; alkylating the thiazoline ring at the 4-carbon position, as indicated in Structural Formula (I), with a compound of the formula R 1 —L, wherein R 1 is as defined above and L is a leaving group, in the presence of a phase transfer catalyst; and, optionally, deprotecting the carboxyl group. In one embodiment of the present invention, a cinchona-alkaloid derived phase transfer catalyst is used to alkylate a protected substituted thiazoline carboxylic acid.

  一种制备烷基化噻唑啉羧酸或其衍生物的有用且高效方法包括：将取代芳基腈（例如2,4-二甲氧基苯腈或4-甲氧基苯腈）与半胱氨酸酯偶合形成取代噻唑啉羧酸酯；可选择水解取代噻唑啉羧酸酯形成取代噻唑啉羧酸；可选择保护羧基；在相转移催化剂存在下，用式R1-L的化合物烷基化噻唑啉环的4-碳位，如结构式（I）所示，其中R1如上所定义，L是一个离去基团；可选择去保护羧基。在本发明的一种实施例中，使用奎宁生物碱衍生的相转移催化剂烷基化保护的取代噻唑啉羧酸。