3-benzylidenethiochroman-4-one

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 硫铬烷
• 英文名称: 3-benzylidenethiochroman-4-one
• 英文别名: 3-benzylidenethiochromen-4-one
• 化学式: C₁₆H₁₂OS
• 分子量: 252.337
• InChiKey: WQEPLGCJMWZKFO-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.9
• 重原子数：
  18
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.06
• 拓扑面积：
  42.4
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  3-benzylidenethiochroman-4-one 、 丙二腈 在 zinc aluminate 作用下， 以 neat (no solvent) 为溶剂， 反应 1.0h， 以86%的产率得到2-amino-4-phenyl<1>benzothio-4H,5H-pyrano<4,3-b>pyran-3-carbonitrile
  参考文献：
  名称：

  ZnAl2O4纳米粉体上的HSBM技术绿色化学制备硫代色素[4,3-b]吡喃和苯并[h]噻唑并[2,3-b]喹唑啉衍生物。

  摘要：

  目的和目的本文的目的是介绍HSBM作为一种绿色环保技术，用于在ZnAl2O4纳米粉体上合成硫代色素[4,3-b]吡喃和苯并[h]噻唑并[2,3-b]喹唑啉衍生物作为有效的催化剂。材料与方法Zn（NO3）2和Al（NO3）3盐的共沉淀法合成了ZnAl2O4纳米粉，并通过XRD，FE-SEM，TEM和DLS技术对其进行了表征。所制备的ZnAl2O4纳米粉已被用作通过高速球磨（HSBM）技术合成吡喃核的催化剂。产物的结构通过NMR分析确认。结果ZnAl2O4呈现立方晶体结构（空间群：Fd-3m），平均晶粒尺寸为41 nm。通过DLS技术测定的ZnAl 2 O 4纳米粉末的平均粒径为55nm。研究了纳米粉体对2-氨基-4,5-二氢-4-芳基硫代色素[4,3-b]吡喃-3-腈，（8Z）-2-氨基-8-亚芳基的合成的催化活性。 -4,5，7,8-四氢-4-芳基硫代吡喃并[4,3-b]吡喃-3-腈，4-芳基-3

  DOI：

  10.2174/1386207322666190617164617
• 作为产物：
  描述：

  硫代色满-4-酮 、 苯甲醛 在 sodium hydroxide 作用下， 以 乙醇 、 水 为溶剂， 生成 3-benzylidenethiochroman-4-one
  参考文献：
  名称：

  BF 3 ·OEt 2介导的串联环空：构建功能化铬和吡喃基吡啶的策略

  摘要：

  描述了一种在BF 3 ·OEt 2存在下简单有效的一环芳基酮，炔烃和腈的方法。在温和的反应条件下以令人满意的产率获得了高度官能化的各种N-取代的吡啶-稠合的色诺和吡喃衍生物。事实证明，该方法可用于合成各种色素铬并[3,4- c ]吡啶，硫代色素[3,4- c ]吡啶，吡喃并[3,4- c ]吡啶和硫代吡喃并[3，来自容易获得的底物的4- c ]吡啶衍生物。这个实验简单的方案在一锅操作中提供了结构复杂，生物学相关的杂环。

  DOI：

  10.1021/acs.joc.7b02463

文献信息

• One-Pot Access to a Library of Dispiro Oxindole-pyrrolidine/pyrrolothiazole-thiochromane Hybrids via Three-Component 1,3-Dipolar Cycloaddition Reactions
  作者：Gandhi Uma Rani、Sundaravel Vivek Kumar、Chelliah Bharkavi、J. Carlos Menéndez、Subbu Perumal

  DOI：10.1021/acscombsci.6b00011

  日期：2016.6.13

  A library of novel dispiro compounds containing oxindole pyrrolidine/oxindolopyrrolothiazole-thiochroman-4-one hybrid frameworks has been synthesized in a fully regio- and stereoselective fashion by the three-component 1,3-dipolar cycloaddition of azomethine ylides generated in situ from the condensation of isatins and secondary amino acids (sarcosine/l-thioproline) with 3-arylidenethiochroman-4-ones

  通过缩合反应中原位生成的三组分1,3-偶极环加成甲硫氨酸以完全区域选择性和立体选择性的方式合成了一个含有二恶唑吡咯烷/恶臭吡咯并噻唑-thiochroman-4-one杂合骨架的新型双螺化合物3-亚芳基亚硫氰酸盐-4-酮对靛红和仲氨基酸（肌氨酸/ 1-硫代脯氨酸）的影响。这个简单的实验方案可在一次操作中提供结构复杂的，生物学上相关的杂环化合物的良好收率。
• BF₃·OEt₂-Mediated Tandem Annulation: A Strategy To Construct Functionalized Chromeno- and Pyrano-Fused Pyridines
  作者：K.T. Ashitha、V. Praveen Kumar、C.T. Fathimath Salfeena、B. S. Sasidhar

  DOI：10.1021/acs.joc.7b02463

  日期：2018.1.5

  variety of N-substituted pyridine-fused chromeno and pyrano derivatives were obtained with satisfactory yields under mild reaction conditions. The method was proven to be valid for the synthesis of a diverse library of chromeno[3,4-c]pyridines, thiochromeno[3,4-c]pyridines, pyrano[3,4-c]pyridines, and thiopyrano[3,4-c]pyridine derivatives from readily accessible substrates. This experimentally simple

  描述了一种在BF 3 ·OEt 2存在下简单有效的一环芳基酮，炔烃和腈的方法。在温和的反应条件下以令人满意的产率获得了高度官能化的各种N-取代的吡啶-稠合的色诺和吡喃衍生物。事实证明，该方法可用于合成各种色素铬并[3,4- c ]吡啶，硫代色素[3,4- c ]吡啶，吡喃并[3,4- c ]吡啶和硫代吡喃并[3，来自容易获得的底物的4- c ]吡啶衍生物。这个实验简单的方案在一锅操作中提供了结构复杂，生物学相关的杂环。
• Antimicrobial Activity and DFT Studies of a Novel Set of Spiropyrrolidines Tethered with Thiochroman-4-one/Chroman-4-one Scaffolds
  作者：Nourhène Chouchène、Amani Toumi、Sarra Boudriga、Hayet Edziri、Mansour Sobeh、Mohamed A. O. Abdelfattah、Moheddine Askri、Michael Knorr、Carsten Strohmann、Lukas Brieger、Armand Soldera

  DOI：10.3390/molecules27030582

  日期：——

  A novel series of 14 spiropyrrolidines bearing thiochroman-4-one/chroman-4-one, and oxindole/acenaphthylene-1,2-dione moieties were synthesized and characterized by spectroscopic techniques, as well as by three X-ray diffraction studies, corroborating the stereochemistry. Quantum chemical calculations studies, using the DFT approach, were performed to rationalize the stereochemical outcome. These N-heterocycles were evaluated for their antibacterial and antifungal activities against some pathogenic organisms. Several compounds displayed moderate to excellent activity towards the screened microbe strains in the study compared to Amoxicillin (AMX), Ampicillin (AMP), and Amphotericin B. Furthermore, a structural activity relationship (SAR) was established considering the synthesized compounds. Pharmacokinetic studies reveal that these derivatives exhibit an acceptable predictive ADMET profile (Absorption, Distribution, Metabolism, Excretion and Toxicity) and good drug-likeness.

  一系列含有硫代色满-4-酮/色满-4-酮和恶唑/乙酰基萘-1,2-二酮基团的14种螺环吡咯烷衍生物被合成并通过光谱技术进行表征，另外三个X射线衍射研究证实了立体化学。采用DFT方法进行量子化学计算研究，以理解立体化学结果。这些N-杂环被评估其对一些病原微生物的抗菌和抗真菌活性。与阿莫西林（AMX），氨苄青霉素（AMP）和两性霉素B相比，几种化合物在研究中对筛选的微生物菌株显示出中等到优异的活性。此外，建立了考虑到合成化合物的结构活性关系（SAR）。药代动力学研究表明，这些衍生物表现出可接受的预测ADMET配置文件（吸收、分布、代谢、排泄和毒性）和良好的药物相似性。
• Construction of polyheterocyclic spirotetrahydrothiophene derivatives via sulfa-Michael/aldol cascade reaction
  作者：Jian-Jun Liang、Jin-Yun Pan、Dong-Cheng Xu、Jian-Wu Xie

  DOI：10.1016/j.tetlet.2014.09.101

  日期：2014.11

  A series of polyheterocyclic spirotetrahydrothiophene derivatives were obtained in moderate to excellent yields via a catalyst-free sulfa-Michael/aldol cascade reaction of chalcones 1 and commercially available 1,4-dithiane-2,5-diol 2 under mild conditions. We also present the first asymmetric sulfa-Michael/aldol cascade reaction of chalcones 1 and commercially available 1,4-dithiane-2,5-diol 2 with moderate to good enantioselectivities catalyzed by readily available chiral phase-transfer catalysts (PTCs). (C) 2014 Elsevier Ltd. All rights reserved.
• Tetralone derivatives are MIF tautomerase inhibitors and attenuate macrophage activation and amplify the hypothermic response in endotoxemic mice
  作者：János Garai、Marcell Krekó、László Őrfi、Péter Balázs Jakus、Zoltán Rumbus、Patrik Kéringer、András Garami、Eszter Vámos、Dominika Kovács、Viola Bagóné Vántus、Balázs Radnai、Tamás Lóránd

  DOI：10.1080/14756366.2021.1916010

  日期：2021.1.1

  Macrophage migration inhibitory factor (MIF) is a pro-inflammatory cytokine playing crucial role in immunity. MIF exerts a unique tautomerase enzymatic activity that has relevance concerning its multiple functions and its small molecule inhibitors have been proven to block its pro-inflammatory effects. Here we demonstrate that some of the E-2-arylmethylene-1-tetralones and their heteroanalogues efficiently bind to MIF's active site and inhibit MIF tautomeric (enolase, ketolase activity) functions. A small set of the synthesised derivatives, namely compounds (4), (23), (24), (26) and (32), reduced inflammatory macrophage activation. Two of the selected compounds (24) and (26), however, markedly inhibited ROS and nitrite production, NF-κB activation, TNF-α, IL-6 and CCL-2 cytokine expression. Pre-treatment of mice with compound (24) exaggerated the hypothermic response to high dose of bacterial endotoxin. Our experiments suggest that tetralones and their derivatives inhibit MIF's tautomeric functions and regulate macrophage activation and thermal changes in severe forms of systemic inflammation.