2-chloro-5-(p-tolyl)pyridine-3-carbaldehyde

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡啶及其衍生物
• 英文名称: 2-chloro-5-(p-tolyl)pyridine-3-carbaldehyde
• 英文别名: 2-Chloro-5-(4-methylphenyl)pyridine-3-carbaldehyde
• 化学式: C₁₃H₁₀ClNO
• 分子量: 231.681
• InChiKey: QYKJLCCYRLBMLK-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.3
• 重原子数：
  16
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.08
• 拓扑面积：
  30
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  2-chloro-5-(p-tolyl)pyridine-3-carbaldehyde 在 甲醇 、 sodium tetrahydroborate 、 copper(ll) sulfate pentahydrate 、 二苯基膦叠氮化物 、 1,8-二氮杂双环[5.4.0]十一碳-7-烯 、 sodium ascorbate 作用下， 以 水 、 甲苯 、 叔丁醇 为溶剂， 反应 17.0h， 生成 5-(((1-((2-chloro-5-p-tolylpyridin-3-yl)methyl)-1H-1,2,3-triazol-4-yl)methoxy)methyl)-3-(3,4,5-trimethoxyphenyl)isoxazole
  参考文献：
  名称：

  Synthesis and structure–activity relationships of pyridinyl-1H-1,2,3-triazolyldihydroisoxazoles as potent inhibitors of tubulin polymerization

  摘要：

  Three series of compounds; pyridinyl-1H-1,2,3-triazoles, pyridinyl-1H-1,2,3-triazolylisoxazoles and pyridinyl-1H-1,2,3-triazolyldihydroisoxazoles with TMP moiety were designed, synthesized and screened for their anti-cancer and anti-tubulin properties. By sequentially designing three series of compounds comprising of dihydroisoxazole in the linker, a small substituent like chlorine on one side (R-1) and aromatic group (R) on the pyridine ring, we have optimized the anti-cancer as well as anti-tubulin activity. Pyridinyl-1H-1,2,3-triazolyldihydroisoxazoles 28b and 28c were found to be potent anti-cancer agents against all the cell lines tested with a concomitant accumulation of cells in the G2/M phase of the cell cycle. Molecular modeling suggests that the trimethoxyphenyl ring in 28b and 28c occupies the cholchicine binding domain of beta-tubulin, whereas, the dihydroisoxazole extends towards the interface of alpha,beta-tubulin. (C) 2014 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2014.11.063
• 作为产物：
  描述：

  4-(p-tolyl)-3-buten-2-one 2-oxime 、 N,N-二甲基甲酰胺 在 三氯氧磷 作用下， 生成 2-chloro-5-(p-tolyl)pyridine-3-carbaldehyde
  参考文献：
  名称：

  在Vilsmeier条件下将共轭肟有效转化为取代的吡啶

  摘要：

  描述了容易合成的吡啶基稠合的甾族D-环和官能化的吡啶。

  DOI：

  10.1016/0040-4039(96)01909-0

文献信息

• Efficient synthesis of isoquinolines and pyridines via copper(i)-catalyzed multi-component reaction
  作者：Kommuri Shekarrao、Partha Pratim Kaishap、Sanjib Gogoi、Romesh C. Boruah

  DOI：10.1039/c3ra46722h

  日期：——

  A wide range of 3-substituted isoquinolines, steroidal pyridines, 5,6-dihydrobenzo[f]isoquinolines and 1,6-naphthyridine were synthesized in good yield via a ligand-free copper-catalyzed three-component reaction of β-halovinyl/aryl aldehyde, aromatic/aliphatic terminal alkyne and tert-butylamine/benzamidine in DMF under microwave irradiation. A catalyst-free reaction of ortho-alkynyl aryl/vinyl aldehydes

  通过无配体铜催化的β-卤代戊基/芳基三组分反应，高收率合成了多种3-取代的异喹啉，甾族吡啶，5,6-二氢苯并[ f ]异喹啉和1,6-萘吡啶微波辐射下，DMF中的乙醛，芳族/脂肪族末端炔烃和叔丁胺/苯甲m 微波辐射下邻炔基芳基/乙烯基醛与苯甲idine的无催化剂反应也以优异的产率提供了3-取代的异喹啉和取代的吡啶衍生物。
• Synthesis and Biological Activities of Nicotinaldehyde Based 1,4-Dihydropyridinedicarboxylates
  作者：K. Suchitra Rani、S. Ramya、K. S. Hariprasad、G. Praveena、A. Zehra、R. S. Prakasham、A. K. Tiwari、B. China Raju

  DOI：10.1134/s1068162021060224

  日期：2021.11

  nicotinaldehydes with aminocrotonoates in the presence of p-TsOH at room temperature. The prepared compounds were evaluated for their anti-microbial, free-radical scavenging and α-glucosidase inhibitory activities. Compounds diethyl 2,6-diphenyl-4-(pyridin-3-yl)-1,4-dihydropyridine-3,5-dicarboxylate and diethyl 4-(2-chloro-5-(4-fluorophenyl)pyridin-3-yl)-2,6-diphenyl-1,4-dihydropyridine-3,5-dicarboxylate were

  摘要 1,4-二氢吡啶羧酸盐是通过烟醛与氨基巴豆酸酯在室温下在p- TsOH存在下反应制备的。对制备的化合物进行了抗微生物、自由基清除和α-葡萄糖苷酶抑制活性的评估。化合物 2,6-二苯基-4-(吡啶-3-基)-1,4-二氢吡啶-3,5-二羧酸二乙酯和4-(2-氯-5-(4-氟苯基)吡啶-3-基二乙酯)-2,6-二苯基-1,4-二氢吡啶-3,5-二羧酸酯被鉴定为有效的抗真菌剂。化合物2,6-二甲基-4-(吡啶-3-基)-1,4-二氢吡啶-3,5-二甲酸二乙酯、4-(2-氯吡啶-3-基)-2,6-二甲基- 1,4-二氢吡啶-3,5-二羧酸酯和 2,6-二甲基-4-(吡啶-4-基)-1,4-二氢吡啶-3,5-二羧酸二乙酯被鉴定为\(\textABT}}\textS}}}^\centerdot + }}}\)自由基清除剂。化合物4-(2-氯-5-苯基吡啶-3-基)-2,6-二苯基-1
• DBU Promoted Facile Synthesis of New Thieno[2,3-<i>b</i>]pyridine/quinoline Derivatives and Their Antimicrobial Evaluation
  作者：Chebolu Naga Sesha Sai Pavan Kumar、Ejjirothu Srihari、Mettu Ravinder、Koochana Pranay Kumar、U. S. N. Murthy、Vaidya Jayathirtha Rao

  DOI：10.1002/jhet.1091

  日期：2013.2

  Several new thieno[2,3-b]pyridine and thieno[2,3-b]quinoline derivatives are synthesized in an efficient manner catalyzed by DBU as a base. Simple workup procedure, good yields, and mild reaction conditions are the salient features of this method. All the synthesized compounds are screened for antimicrobial activity against several organisms.

  几个新 噻吩并[2,3- b ]吡啶和噻吩并[2,3- b ]喹啉衍生物是以DBU为碱催化的高效合成方法。简单的后处理程序，良好的收率和温和的反应条件是该方法的主要特征。筛选所有合成的化合物对几种生物的抗菌活性。
• Anti-proliferative, structure–activity relationship of pyridinylchalcones and chromanones
  作者：Cherupally Dayakar、Pathi Suman、Kommera Rajkumar、Thampunuri Ramalinga Murthy、Shasi Vardhan Kalivendi、Bhimapaka China Raju

  DOI：10.1007/s00044-017-2034-3

  日期：2018.1

  might be responsible in 3e induced apoptosis. Graphical AbstractPyridinylchalcones, chromanones were screened for their in vitro anti-proliferative activity against four human cancer cell lines by the standard 3-(4,5-dimethylthiazol-2-yl)-2,5-diphenyltetrazolium bromide assay method. Pyridinylchalcones and chromanones exhibited IC50 values in the range of 5.9–289 µM. Compound 3e exhibited an IC50 of

  摘要一系列pyridinylchalcones的图3a - q，二氢吡喃4A - q制备并筛选针对四种人类肿瘤细胞系的体外抗增殖活性即。，宫颈癌（HeLa细胞），肺腺癌（A549），前列腺（DU-145）和乳房（MDA-MB-231）。吡啶基查耳酮3a-q和发色酮4a-q的IC 50值为5.9–289 µM。在HeLa细胞系中，化合物3e的IC 50为5.9 µM，在10 µM的浓度下caspase-3活性也增加到2.7倍。细胞周期分析进一步证实了3e的凋亡作用由于细胞周期亚G1期停滞的细胞大量增加。此外，在3e处理的细胞中线粒体膜电位的丧失表明细胞凋亡的内在途径可能与3e诱导的细胞凋亡有关。 图形概要通过标准3-（4,5-二甲基噻唑-2-基）-2,5-二苯基四唑溴化物测定方法，筛选出吡啶基查耳酮，发色酮对四种人类癌细胞的体外抗增殖活性。吡啶基查耳酮和苯并二氢吡喃酮的IC 50值为5.9–289
• A Rapid and Convenient Microwave-Promoted Synthesis of 3,5-Disubstituted 2-Chloropyridines and Their Conversion into Tetrazolo[1,5-a]pyridines
  作者：Romesh Boruah、Shyamalee Gogoi、Sanjib Gogoi

  DOI：10.1055/s-0032-1317930

  日期：——

  2-chloropyridines from various α,β-unsaturated ketoximes utilizing the Vilsmeier reaction under microwave irradiation. The 3,5-disubstituted 2-chloropyridines were further converted into tetrazolo[1,5-a]pyridines by a microwave-mediated solid-phase reaction. The products were isolated in good yields within a very short reaction time. This work describes a rapid and convenient synthesis of 3,5-disubstituted

  摘要 这项工作描述了在微波辐射下利用Vilsmeier反应从各种α，β-不饱和酮肟快速，方便地合成3,5-二取代的2-氯吡啶。通过微波介导的固相反应，将3，5-二取代的2-氯吡啶进一步转化为四唑并[1，5- a ]吡啶。在非常短的反应时间内以高收率分离出产物。 这项工作描述了在微波辐射下利用Vilsmeier反应从各种α，β-不饱和酮肟快速，方便地合成3,5-二取代的2-氯吡啶。通过微波介导的固相反应，将3，5-二取代的2-氯吡啶进一步转化为四唑并[1，5- a ]吡啶。在非常短的反应时间内以高收率分离出产物。