5-(4-氯苯基)噻吩-2-甲醛 | 38401-71-7

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 中文名称: 5-(4-氯苯基)噻吩-2-甲醛
• 英文名称: 5-(4-chlorophenyl)thiophene-2-carbaldehyde
• CAS: 38401-71-7
• 化学式: C₁₁H₇ClOS
• mdl: MFCD01860767
• 分子量: 222.695
• InChiKey: JFAKPLYPDADDKE-UHFFFAOYSA-N

物化性质

• 熔点：
  85-86°C

计算性质

• 辛醇/水分配系数(LogP)：
  3.7
• 重原子数：
  14
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  45.3
• 氢给体数：
  0
• 氢受体数：
  2

安全信息

• 危险等级：
  IRRITANT
• 危险品标志：
  Xi
• 海关编码：
  2934999090
• WGK Germany：
  3
• 储存条件：
  2-8°C

反应信息

• 作为反应物：
  描述：

  5-(4-氯苯基)噻吩-2-甲醛 在 六甲基磷酰三胺 、 sodium hydroxide 、 lithium aluminium tetrahydride 、 氯化亚砜 、 硫酸 、 silver(l) oxide 作用下， 以 四氢呋喃 、 乙醚 、 水 、 甲苯 为溶剂， 反应 7.0h， 生成 2-(Chloromethyl)-5-(4-chlorophenyl)thiophene
  参考文献：
  名称：

  Synthesis and structure–activity relationships of 5-phenylthiophenecarboxylic acid derivatives as antirheumatic agents

  摘要：

  5-(Phenylthiophene)-3-carboxylic acid (2a), a metabolite of esonarimod (1), which was developed as a new antirheumatic drug, was considered as a lead compound for new antirheumatic drugs. A new series of 2a derivatives were synthesized and their characteristic pharmacological effects, that is their antagonistic effect toward interleukin (IL)-1 in mice and the suppressive effect against adjuvant-induced arthritis (AIA) in rats, were evaluated and compared with those of 1. The structure-activity relationships indicated that [5-(4-bromophenyl)- thiophen-3-yl]acetic acid (5d), methyl [5-(4-chlorophenyl)-thiophen-3-yl]acetate acid (5d), and methyl [5-(4-bromophenyl)-thiophen-3-yl]acetate (5i) suppressed AIA more potently than 1 and all of the other synthesized compounds. (C) 2003 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2003.08.009
• 作为产物：
  描述：

  4,4'-二氯苯丁酮 在 硫酸 、 三氯氧磷 作用下， 以 甲醇 、 1,2-二氯乙烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 42.0h， 生成 5-(4-氯苯基)噻吩-2-甲醛
  参考文献：
  名称：

  Synthesis and structure–activity relationships of 5-phenylthiophenecarboxylic acid derivatives as antirheumatic agents

  摘要：

  5-(Phenylthiophene)-3-carboxylic acid (2a), a metabolite of esonarimod (1), which was developed as a new antirheumatic drug, was considered as a lead compound for new antirheumatic drugs. A new series of 2a derivatives were synthesized and their characteristic pharmacological effects, that is their antagonistic effect toward interleukin (IL)-1 in mice and the suppressive effect against adjuvant-induced arthritis (AIA) in rats, were evaluated and compared with those of 1. The structure-activity relationships indicated that [5-(4-bromophenyl)- thiophen-3-yl]acetic acid (5d), methyl [5-(4-chlorophenyl)-thiophen-3-yl]acetate acid (5d), and methyl [5-(4-bromophenyl)-thiophen-3-yl]acetate (5i) suppressed AIA more potently than 1 and all of the other synthesized compounds. (C) 2003 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2003.08.009

文献信息

• [EN] HERBICIDALLY ACTIVE HETEROARYL-S?BSTIT?TED CYCLIC DIONES OR DERIVATIVES THEREOF<br/>[FR] DIONES CYCLIQUES SUBSTITUÉES PAR HÉTÉROARYLE À ACTIVITÉ HERBICIDE OU DÉRIVÉS DE CELLES-CI
  申请人：SYNGENTA LTD

  公开号：WO2011012862A1

  公开（公告）日：2011-02-03

  The invention relates to a compound of formula (I), which is suitable for use as a herbicide wherein G is hydrogen or an agriculturally acceptable metal, sulfonium, ammonium or latentiating group; Q is a unsubstituted or substituted C3-C8 saturated or mono-unsaturated heterocyclyl containing at least one heteroatom selected from O, N and S, or Q is heteroaryl or substituted heteroaryl; m is 1, 2 or 3; and Het is an optionally substituted monocyclic or bicyclic heteroaromatic ring; and wherein the compound is optionally an agronomically acceptable salt thereof.

  该发明涉及一种化合物，其化学式为(I)，适用作为除草剂，其中G为氢或农业可接受的金属、磺酸盐、铵盐或潜伏基团；Q为未取代或取代的含有至少一个来自O、N和S的杂原子的饱和或单不饱和的C3-C8杂环烷基，或Q为杂芳基或取代的杂芳基；m为1、2或3；Het为可选择地取代的单环或双环杂芳环；且该化合物可选择地为其农学上可接受的盐。
• An expedient synthesis of thienylacetic acids using the Willgerodt-Kindler reaction under PTC conditions
  作者：Vitaly A. Podshibyakin、Evgenii N. Shepelenko、Karina S. Tikhomirova、Alexander D. Dubonosov、Vladimir A. Bren、Vladimir I. Minkin

  DOI：10.24820/ark.5550190.p009.901

  日期：——

  Novel (5-aryl-2-methylthiophen-3-yl)acetic acids were synthesized starting from 3-aryl-3chloroacrylaldehydes via corresponding thienylcarbaldehydes and thienylethanones using Willgerodt-Kindler reaction under phase-transfer conditions. Their structures were established based on the data of H, C NMR, IR spectroscopy and mass-spectrometry.

  在相转移条件下使用 Willgerodt-Kindler 反应，以 3-芳基-3 氯丙烯醛为原料，通过相应的噻吩基甲醛和噻吩基乙酮合成了新型 (5-芳基-2-甲基噻吩-3-基) 乙酸。它们的结构是根据H、C NMR、IR光谱和质谱数据确定的。
• Metal-Free Aerobic Oxidative Selective C–C Bond Cleavage in Heteroaryl-Containing Primary and Secondary Alcohols
  作者：Anjie Xia、Xueyu Qi、Xin Mao、Xiaoai Wu、Xin Yang、Rong Zhang、Zhiyu Xiang、Zhong Lian、Yingchun Chen、Shengyong Yang

  DOI：10.1021/acs.orglett.9b00563

  日期：2019.5.3

  aerobic oxidative selective C–C bond-cleavage reaction in primary and secondary heteroaryl alcohols is reported. This reaction was highly efficient and tolerated various heteroaryl alcohols, generating a carboxylic acid derivative and a neutral heteroaromatic compound. Experimental studies combined with density functional theory calculations revealed the mechanism underlying the selective C–C bond

  据报道，伯和仲杂芳基醇中无过渡金属的需氧氧化选择性C–C键断裂反应。该反应是高效的并且耐受各种杂芳基醇，产生羧酸衍生物和中性杂芳族化合物。实验研究与密度泛函理论计算相结合，揭示了选择性C–C键断裂的机理。该策略还提供了另一种简单的羧化反应方法。
• [EN] COMPOUNDS, PREPARATIONS AND USES THEREOF<br/>[FR] COMPOSÉS, LEURS PRÉPARATIONS ET LEURS UTILISATIONS
  申请人：PETER MACCALLUM CANCER INST

  公开号：WO2011075784A1

  公开（公告）日：2011-06-30

  The present invention provides novel compounds of the Formula (I), pharmaceutical compositions comprising such compounds and methods for using such compounds as agents or drugs for inhibiting perforin activity and for treating a subject at risk of or susceptible to a disease or disorder, or having a disease or disorder associated with undesirable perforin activity.

  本发明提供了式（I）的新化合物，包括这些化合物的药物组合物以及使用这些化合物作为抑制穿孔素活性的药剂或药物，用于治疗患有与不良穿孔素活性相关的疾病或紊乱、或处于患有风险或易感染某种疾病或紊乱的受试者的方法。
• Discovery of selective protein arginine methyltransferase 5 inhibitors and biological evaluations
  作者：Sen Ji、Shuang Ma、Wen-Jing Wang、Shen-Zhen Huang、Tian-qi Wang、Rong Xiang、Yi-Guo Hu、Qiang Chen、Lin-Li Li、Sheng-Yong Yang

  DOI：10.1111/cbdd.12881

  日期：2017.4

  PRMT5 is an important protein arginine methyltransferase that catalyzes the symmetric dimethylation of arginine resides on histones or non-histone substrate proteins. It has been thought as a promising target for many diseases, particularly cancer. Despite the potential applications of PRMT5 inhibitors in cancer treatment, very few of PRMT5i have been publicly reported. In this investigation, virtual

  PRMT5是一种重要的蛋白质精氨酸甲基转移酶，可催化组蛋白或非组蛋白底物蛋白质上的精氨酸对称二甲基化。人们认为它是许多疾病，特别是癌症的有希望的靶标。尽管PRMT5抑制剂在癌症治疗中有潜在的应用，但PRMT5i很少公开报道。在这项调查中，进行了虚拟筛选和结构-活性关系（SAR）研究，以发现新型PRMT5i，最终导致鉴定出许多新的PRMT5i。最具活性的化合物P5i-6对PRMT5表现出相当大的抑制效能，IC50值为0.57μM，对PRMT5对其他测试PRMT的选择性也很高。它对两种结直肠癌细胞系显示出非常好的抗活力，HT-29和DLD-1，以及一种肝癌细胞系HepG2，针对36种不同的癌细胞系进行了敏感性分析。Western Blot分析表明，P5i-6选择性抑制DLD-1细胞中H4R3和H3R8的对称二甲基化。总体而言，P5i-6可以用作化学探针，以研究PRMT​​5在生物学中的新功能，