[(E)-[(3-Bbromophenyl)methylidene]amino]thiourea

• 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: [(E)-[(3-Bbromophenyl)methylidene]amino]thiourea
• 英文别名: 3-bromophenylcarbaldehyde (E)-thiosemicarbazone；2-(3-bromobenzylidene)hydrazinecarbothioamide；(E)-2-(3-bromobenzylidene)hydrazinecarbothioamide；(E)-3-bromobenzaldehyde thiosemicarbazone；(E)-1-(3-bromobenzylidene)thiosemicarbazide；3-bromobenzaldehyde thio semicarbazone；3-Bromobenzaldehyde thiosemicarbazone；[(E)-(3-bromophenyl)methylideneamino]thiourea
• 化学式: C₈H₈BrN₃S
• 分子量: 258.142
• InChiKey: FGGWIXJNLRDBPW-VZUCSPMQSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  13
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  82.5
• 氢给体数：
  2
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  2-氯乙酰乙酸乙酯 、 [(E)-[(3-Bbromophenyl)methylidene]amino]thiourea 以 乙醇 为溶剂， 以82%的产率得到ethyl 2-[(E)-2-[(3-bromophenyl)methylidene]hydrazin-1-yl]-4-methyl-1,3-thiazole-5-carboxylate
  参考文献：
  名称：

  2-(2-Hydrazinyl)thiazole derivatives: Design, synthesis and in vitro antimycobacterial studies

  摘要：

  In an attempt to discover new potent inhibitors for Mycobacterium tuberculosis (Mtb), a series of 2-(2hydrazinyl)thiazole derivatives with a wide range of substitutions at 2-, 4- and 5-positions were designed by considering Lipinski rule. The designed compounds were synthesized, characterized and evaluated for their inhibitory potential against Mtb, H(37)Rv, by in vitro assay. The compounds, ethyl-4methyl-2-[(E)-24]-(pyridin-2-yl)ethylidene]hydrazin-1-yl]-1,3-thiazole-5-carboxylate, 4d, and ethyl-2[(E)-2-[(2-hydroxyphenyl)methylidenelhydrazin-1-yl]-4-methyl-1,3-thiazole-5-carboxylate, 2i showed noticeable inhibitory activity against Mtb, H37Rv with minimum inhibitory concentration (MIC) of 12.5 pM and 25 1.1M respectively. An attempt has been made to understand the mechanism of action by binding interactions of these molecules with 0-ketoacyl-ACP synthase protein through docking studies. The inhibition constants for compounds 4d and 2i were found to be 1.46 pM and 0.177 pM respectively. (C) 2013 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2013.08.054
• 作为产物：
  描述：

  间溴苯甲醛 、 氨基硫脲 在 溶剂黄146 作用下， 以 乙醇 、 水 为溶剂， 反应 24.0h， 以98%的产率得到[(E)-[(3-Bbromophenyl)methylidene]amino]thiourea
  参考文献：
  名称：

  Synthesis and Single-Crystal X-Ray Diffraction Studies of an Arylidenethiosemicarbazone and Hydrazonyl-phenylthiazole

  摘要：

  芳香醛与氨基硫脲反应生成亚苯基酰肼硫酰胺，其与苯乙酰溴反应生成（亚苯基酰肼基）-4-苯基噻唑。通过1H-NMR和质谱技术全面表征了3和7的结构。光谱分析与所指派的结构一致。所指派的结构进一步得到了单晶X射线衍射研究的支持，总结如下：3为三斜晶系，P-1空间群，a=7.6319(4) Å，b=8.7099(4) Å，c=10.7145(5) Å，α=77.7400(10)°，β=74.0160(10)°，γ=72.8270(10)°，V=647.47(5) ų，Z=2；7为正交晶系，Pna21空间群，a=9.3760(13) Å，b=14.029(2) Å，c=23.591(3) Å，α=90°，β=90°，γ=90°，V=3103.0(7) ų，Z=4。

  DOI：

  10.2174/15701786113106660065

文献信息

• Design, Synthesis, and Evaluation of 3-((4-(<i>t</i>-Butyl)-2-(2-benzylidenehydrazinyl)thiazol-5-yl)methyl)quinolin-2(1<i>H</i>)-ones as Neuraminidase Inhibitors
  作者：Yilin Fang、Mengwu Xiao、Aixi Hu、Jiao Ye、Wenwen Lian、Ailin Liu

  DOI：10.1002/cjoc.201500738

  日期：2016.4

  A series of novel 3‐((4‐(t‐butyl)‐2‐(2‐benzylidenehydrazinyl)thiazol‐5‐yl)methyl)quinolin‐2(1H)‐ones (7a–7z) were designed, synthesized and evaluated for their ability of inhibiting neuraminidase (NA) of in?uenza H1N1 virus. Some compounds displayed moderate influenza NA inhibitory activity. Compound 7l with the scaffold of 2‐(2‐(2‐methoxybenzylidene)hydrazinyl)thiazole was the best one, exhibiting

  设计，合成和合成了一系列新颖的3-（（4-（叔丁基）-2-（2-苄叉肼基）噻唑-5-基）甲基）喹啉-2-（1 H）-酮（7a - 7z）评估其抑制流感H1N1病毒神经氨酸酶（NA）的能力。一些化合物显示出中等的流感NA抑制活性。带有7-（2-（2-（2-甲氧基亚苄基）肼基）噻唑骨架的化合物7l是最好的化合物，具有中等的NA抑制活性，IC 50为44.66 µmol / L。结构-活性关系显示出与甲氧基或羟基基团的化合物在邻位，氟和硝基在元苯环对位的氯和溴基更活泼。对接研究表明，化合物7l与一些关键残基（包括Asp151，Glu119，Arg292，Tyr406和Asn347）具有重要的相互作用，并与邻近NA活性位点的430腔结合。
• Synthesis, NMR structural characterization and molecular modeling of substituted thiosemicarbazones and semicarbazones using DFT calculations to prove the syn/anti isomer formation
  作者：T. K. Venkatachalam、Gregory K. Pierens、David C. Reutens

  DOI：10.1002/mrc.4041

  日期：2014.3

  Thiosemicarbazones possessing electron‐donating and electron‐withdrawing groups were prepared, and their spectral characteristics determined. In all cases, the spectra showed that one isomer was formed, allowing further functionalization to molecules of biological interest. We provide NMR data for some of the thiosemicarbazones and semicarbazones. We also provide evidence that for 2‐pyridyl thiosemicarbazone

  制备了具有给电子和吸电子基团的硫缩氨基脲，并确定了它们的光谱特性。在所有情况下，光谱都表明形成了一种异构体，从而可以进一步功能化具有生物学意义的分子。我们提供了一些缩氨基硫脲和缩氨基脲的核磁共振数据。我们还提供证据表明，对于 2-吡啶基缩氨基硫脲，顺式异构体在二甲亚砜溶剂中以一级动力学缓慢转化为反式异构体。分子建模和密度泛函理论计算证实了这些观察结果。版权所有 © 2014 John Wiley & Sons, Ltd.
• Synthesis and Single-Crystal X-Ray Diffraction Studies of an Arylidenethiosemicarbazone and Hydrazonyl-phenylthiazole
  作者：El Ashry、Sammer Yousuf、Hayat Hassan、Magdy Zahran、Ali Hebishy

  DOI：10.2174/15701786113106660065

  日期：2014.1.31

  The reaction of aromatic aldehydes with thiosemicarbazide gives arylidene hydrazinecarbothioamide, whose reaction with phenacyl bromide, yielded (arylidenehydrazonyl)-4-phenylthiazole. The structures of 3 and 7 were fully characterized by using 1H-NMR and mass spectroscopic techniques. The spectral analysis agreed with the assigned structures. The assigned structures were further supported by single-crystal X-ray diffraction studies and summarized as follows: (3) Triclinic, P-1, a=7.6319(4) Å, b= 8.7099(4) Å, c=10.7145(5) Å, α= 77.7400 (10)°, β= 74.0160 (10)°, and γ= 72.8270 (10)°, V= 647.47(5) Å3, and Z = 2; (7) Orthorhombic, Pna21, a = 9.3760(13), b = 14.029(2), c = 23.591(3)Å, α=90, β= 90, and γ= 90o, V = 3103.0(7)Å3, and Z = 4.

  芳香醛与氨基硫脲反应生成亚苯基酰肼硫酰胺，其与苯乙酰溴反应生成（亚苯基酰肼基）-4-苯基噻唑。通过1H-NMR和质谱技术全面表征了3和7的结构。光谱分析与所指派的结构一致。所指派的结构进一步得到了单晶X射线衍射研究的支持，总结如下：3为三斜晶系，P-1空间群，a=7.6319(4) Å，b=8.7099(4) Å，c=10.7145(5) Å，α=77.7400(10)°，β=74.0160(10)°，γ=72.8270(10)°，V=647.47(5) ų，Z=2；7为正交晶系，Pna21空间群，a=9.3760(13) Å，b=14.029(2) Å，c=23.591(3) Å，α=90°，β=90°，γ=90°，V=3103.0(7) ų，Z=4。
• Aryl thiosemicarbazones for the treatment of trypanosomatidic infections
  作者：Pasquale Linciano、Carolina B. Moraes、Laura M. Alcantara、Caio H. Franco、Bruno Pascoalino、Lucio H. Freitas-Junior、Sara Macedo、Nuno Santarem、Anabela Cordeiro-da-Silva、Sheraz Gul、Gesa Witt、Maria Kuzikov、Bernhard Ellinger、Stefania Ferrari、Rosaria Luciani、Antonio Quotadamo、Luca Costantino、Maria Paola Costi

  DOI：10.1016/j.ejmech.2018.01.043

  日期：2018.2

  interesting activity against the same organisms. The compounds were particularly effective against T. brucei and T. cruzi. Among the 28 synthesized compounds, the best one was (E)-2-(4-((3.4-dichlorobenzyl)oxy)benzylidene) hydrazinecarbothioamide (A14) yielding a comparable anti-parasitic activity against the three parasitic species (TbEC50 = 2.31 μM, LiEC50 = 6.14 μM, TcEC50 = 1.31 μM) and a Selectivity Index

  基于显示出抗锥虫病活性的噻二唑衍生物库，我们已经考虑了噻二唑的开放形式和反应中间体硫代半脲类化合物，作为针对布鲁氏锥虫（Tb），婴儿利什曼原虫（Li）和克氏锥虫（Tc）。相似的化合物已经显示出对相同生物的有趣活性。该化合物对T. brucei和T. cruzi特别有效。在这28种合成的化合物中，最好的一种是（E）-2-（4-（（3.4-二氯苄基）氧基）亚苄基）肼基甲硫代酰胺（A14）针对三种寄生物（Tb EC 50  = 2.31μM，Li EC 50  = 6.14μM，Tc EC 50  = 1.31μM ）产生可比的抗寄生虫活性，并且相对于人类巨噬细胞的选择性指数高于10，因此显示泛抗锥虫病活动。（E）-2-（（（3'.4'-二甲氧基-[1.1'-联苯] -3-基]甲基）甲基）肼基甲硫代酰胺（A12）和（E）-2-（4-（（3.4-二氯苄基）氧基）苯亚甲基）肼硫代甲酰胺（A14）在组
• Thio semicarbazone and semicarbazone inhibitors of cysteine proteases and methods of their use
  申请人：The Regents of the University of California

  公开号：US20040014801A1

  公开（公告）日：2004-01-22

  The present invention relates to thio semicarbazone and semicarbazone inhibitors of cysteine proteases and methods of using such compounds to prevent and treat protozoan infections such as trypanosomiasis, malaria and leishmaniasis. The compounds also find use in inhibiting cysteine proteases associated with carcinogenesis, including cathepsins B and L.

  本发明涉及硫代半卡巴酮和半卡巴酮对半胱氨酸蛋白酶的抑制剂，以及使用这些化合物预防和治疗原生动物感染，如锥虫病、疟疾和利什曼病的方法。这些化合物还可用于抑制与癌变有关的半胱氨酸蛋白酶，包括卡特普辛B和L。