4-(4-甲氧基苄基)-3-氨基硫脲 | 16735-76-5

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 中文名称: 4-(4-甲氧基苄基)-3-氨基硫脲
• 英文名称: N-(4-methoxybenzyl)hydrazinecarbothioamide
• 英文别名: 4-(4-methoxybenzyl)-3-thiosemicarbazide；N-(4-methoxybenzyl)-thiosemicarbazide；4-(4-methoxy-benzyl)-thiosemicarbazide；4-(4-Methoxy-benzyl)-thiosemicarbazid；4-(p-methoxybenzyl)-thiosemicarbazide；N-p-Methoxybenzyl-thiosemicarbazid；1-amino-3-[(4-methoxyphenyl)methyl]thiourea
• CAS: 16735-76-5
• 化学式: C₉H₁₃N₃OS
• mdl: MFCD00060591
• 分子量: 211.288
• InChiKey: RJYHJXVBSQAYNL-UHFFFAOYSA-N

物化性质

• 熔点：
  131-133°C
• 沸点：
  362.5±44.0 °C(Predicted)
• 密度：
  1.224±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.7
• 重原子数：
  14
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.222
• 拓扑面积：
  91.4
• 氢给体数：
  3
• 氢受体数：
  3

安全信息

• 危险等级：
  IRRITANT
• 危险类别码：
  R23/24/25
• 危险品运输编号：
  UN 2811
• 海关编码：
  2930909090
• 危险类别：
  IRRITANT
• 安全说明：
  S22,S36/37/39

反应信息

• 作为反应物：
  描述：

  4-(4-甲氧基苄基)-3-氨基硫脲 在 caesium carbonate 、 N,N'-羰基二咪唑 作用下， 以 1,4-二氧六环 、 N,N-二甲基甲酰胺 为溶剂， 反应 5.0h， 生成 3-(4-bromo-2,5-difluorophenyl)-5-((cyclopropylmethyl)thio)-4-(4-methoxybenzyl)-4H-1,2,4-triazole
  参考文献：
  名称：

  1,2,4-Triazolsulfone: A novel isosteric replacement of acylsulfonamides in the context of Na V 1.7 inhibition

  摘要：

  Recently, the identification of several classes of aryl sulfonamides and acyl sulfonamides that potently inhibit Na(v)1.7 and demonstrate high levels of selectivity over other Na-v isoforms have been reported. The fully ionizable nature of these inhibitors has been shown to be an important part of the pharmacophore for the observed potency and isoform selectivity. The requirement of this functionality, however, has presented challenges associated with optimization toward inhibitors with drug-like properties and minimal off-target activity. In an effort to obviate these challenges, we set out to develop an orally bioavailable, selective Na(v)1.7 inhibitor, lacking these acidic functional groups. Herein, we report the discovery of a novel series of inhibitors wherein a triazolesulfone has been designed to serve as a bioisostere for the acyl sulfonamide. This work culminated in the delivery of a potent series of inhibitors which demonstrated good levels of selectivity over Na v 1.5 and favorable pharmacokinetics in rodents. (C) 2018 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2018.04.035
• 作为产物：
  描述：

  4-甲氧基苄基异硫氰酸酯 在 肼 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 生成 4-(4-甲氧基苄基)-3-氨基硫脲
  参考文献：
  名称：

  Synthesis and optimization of thiadiazole derivatives as a novel class of substrate competitive c-Jun N-terminal kinase inhibitors

  摘要：

  A series of thiadiazole derivatives has been designed as potential allosteric, substrate competitive inhibitors of the protein kinase JNK. We report on the synthesis, characterization and evaluation of a series of compounds that resulted in the identification of potent and selective JNK inhibitors targeting its JIP-1 docking site. (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2009.12.013

文献信息

• [EN] OXAZOLIDINONE DERIVATES N-SUBSTITUTED BY A TRICYCLIC RING, FOR USE AS ANTIBACTERIAL AGENTS<br/>[FR] DERIVES D'OXAZOLIDINONES N-SUBSTITUES PAR UN NOYAU TRICYCLIQUE, DESTINES A ETRE UTILISES EN TANT QU'AGENTS ANTIBACTERIENS
  申请人：WARNER LAMBERT CO

  公开号：WO2004069245A1

  公开（公告）日：2004-08-19

  Compounds of formula (I) and methods for their preparation are disclosed. Further disclosed are methods of making biologically active compounds of formula (I) as well as pharmaceutically acceptable compositions comprising compounds of formula (I). Compounds of formula (I) as disclosed herein can be used in a variety of applications including use as antibacterial P is a tricyclic ring system as defined in claiml.

  公式（I）的化合物及其制备方法已被披露。进一步披露了制备公式（I）生物活性化合物的方法，以及包含公式（I）化合物的药用可接受组合物的方法。本文披露的公式（I）化合物可用于各种应用，包括用作抗菌剂P是在权利要求1中定义的三环环系统。
• Ferrocene-based thiosemicarbazones: Solvent effect on thiol-thione tautomerism and conformational polymorphism
  作者：Mazhar Hussain、Riffat Jawaria、Zahid Shafiq、Ghulam Abbas、Muhammad Moazzam Naseer

  DOI：10.1016/j.jorganchem.2017.05.005

  日期：2017.10

  important molecules with tremendous biological significance. In the present study, effect of solvents of different nature and polarity on thiol-thione tautomerism in ferrocene-based thiosemicarbazones 1–3 has been evaluated though UV-vis spectroscopy. The resulting data shows a good correlation between the tautomer and the polarity of the solvent. The hydrogen bond donating or accepting ability of

  硫代氨基脲是重要的分子，具有重要的生物学意义。在本研究中，已通过紫外可见分光光度法评估了不同性质和极性的溶剂对二茂铁基硫代半氨基甲酮1-3中硫醇-硫酮互变异构的影响。所得数据显示互变异构体与溶剂极性之间的良好相关性。如果不考虑取代基，则溶剂的氢键赋予或接受能力在优先稳定一种互变异构体中没有发挥任何主要作用。有了这些信息，就尝试在不同的溶剂中寻找1至3的趋同性。然而，尽管desmotrops的，构象多态性的一个有趣的案例1已被发现。在晶体生长的条件略有不同的情况下，已获得两个1的多晶型物，这是由于中心N-亚氨基硫脲部分周围的二茂铁基和芳基取代基的取向不同而具有不同的，并且其晶胞参数略有不同。有趣的是，这两种多晶型物具有几乎相同的3D晶体堆积，这在固态化学中是非常罕见的现象。另外，还讨论了2和3的固态自组装。
• Cephalosporin derivatives
  申请人：Pfizer Inc.

  公开号：US04080451A1

  公开（公告）日：1978-03-21

  A series of novel 7-(D.alpha.-aminophenylacetamido)- and 7-(D-.alpha.-hydroxyphenylacetamido)- .DELTA..sup.3 -cephem derivatives have been prepared wherein a heterocyclic thiomethyl moiety is located at the 3-position of the molecule. These compounds are useful as antibacterial agents for the treatment of diseases caused by Gram-positive and Gram-negative bacteria. Preferred members include 7-(D-.alpha.-hydroxyphenylacetamido)-3-(3-carbamoyl-1,2,4-triazol-5-yl)thi omethylceph-3-em-4-carboxylic acid and 7-(D-.alpha.-hydroxyphenylacetamido)-3-(2-carboxymethoxy-methyl-1,3,4-thia diazol-5-yl)thiomethylceph-3-em-4-carboxylic acid. Alternative methods of preparation are provided for these compounds, including various synthetic routes leading to the required novel heterocyclic thiol intermediates.

  已制备了一系列新型7-(D.α.-氨基苯乙酰胺基)-和7-(D.α.-羟基苯乙酰胺基)-Δ3-头孢菌素衍生物，其中杂环硫甲基基团位于分子的3位。这些化合物可用作抗菌剂，用于治疗由革兰氏阳性和革兰氏阴性细菌引起的疾病。首选成员包括7-(D.α.-羟基苯乙酰胺基)-3-(3-氨基甲酰-1,2,4-三唑-5-基)硫甲基头孢-3-酮-4-羧酸和7-(D.α.-羟基苯乙酰胺基)-3-(2-羧甲氧甲基-1,3,4-噻二唑-5-基)硫甲基头孢-3-酮-4-羧酸。提供了这些化合物的替代制备方法，包括导致所需新型杂环硫醇中间体的各种合成路线。
• Synthesis, X-ray molecular structure, biological evaluation and molecular docking studies of some N 4 -benzyl substituted 5-nitroisatin-3-thiosemicarbazones
  作者：Humayun Pervez、Nazia Khan、Sumera Zaib、Muhammad Yaqub、Muhammad Moazzam Naseer、Muhammad Nawaz Tahir、Jamshed Iqbal

  DOI：10.1016/j.bmc.2016.12.012

  日期：2017.2

  as persuasive leads for further studies. In phytotoxicity assay, twelve out of fifteen thiosemicarbazones tested i.e. 5a–e, 5g, 5i and 5k–o appeared to be active, exhibiting weak or non-significant (5–35%) growth inhibition at the highest tested concentrations (1000 or 500 μg/mL). In contrast, only one compound i.e. 5i was active in the brine shrimp (Artemia salina) lethality bioassay, demonstrating

  合成了一系列的十五个N 4-苄基取代的5-硝基异丁香3-硫代半金属咔唑5a - o并评估了其对脲酶的抑制，植物毒性和细胞毒性的影响。所有化合物 均被证明是该酶的高效抑制剂，显示出抑制活性（IC 50 = 0.87±0.25–8.09±0.23μM）比参考抑制剂硫脲（IC 50  = 22.3± 1.12μM）好得多，因此可以发挥作用作为有说服力的线索，可以进一步研究。在植物毒性测定中，测试了15种硫半脲中的12种，即5a - e，5g，5i和5k - o似乎是活跃的，在最高测试浓度（1000或500μg/ mL）下，表现出微弱或不显着的生长抑制（5-35％）。相反，盐水虾（卤虫）的致死性生物测定中只有一种化合物（即5i）具有活性，显示了LD 50值为2.55×10 -5  M的细胞毒性活性。还对化合物5a – o进行了分子对接研究，以确定它们的可能存在。酶活性位点的结合方式。
• Synthesis, crystal structure, molecular docking studies and bio-evaluation of some <i>N</i> ⁴-benzyl-substituted isatin- 3-thiosemicarbazones as urease and glycation inhibitors
  作者：Humayun Pervez、Nazia Khan、Jamshed Iqbal、Sumera Zaib、Muhammad Yaqub、Muhammad Nawaz Tahir、Muhammad Moazzam Naseer

  DOI：10.1515/hc-2017-0148

  日期：2018.2.23

  Abstract Fifteen N4-benzyl-substituted isatin-3-thiosemicarbazones 5a–o were synthesized and evaluated for their urease and glycation inhibitory potential. Lemna aequinocitalis growth and Artemia salina assays were also done to determine their phytotoxic and toxic effects. All compounds are potent inhibitors of the urease enzyme, displaying inhibition [half maximal inhibitory concentration (IC50)=1

  摘要 合成了 15 种 N4-苄基取代的靛红-3-缩氨基硫脲 5a-o，并评估了它们的脲酶和糖基化抑制潜力。还进行了 Lemna aequinocitalis 生长和卤虫试验以确定它们的植物毒性和毒性作用。所有化合物都是脲酶的有效抑制剂，显示抑制作用 [半数最大抑制浓度 (IC50)=1.08±0.12–11.23±0.19 μm] 优于参考抑制剂硫脲 (IC50=22.3±1.12 μm)。化合物 5c、5d、5h、5j、k 是有效的抗糖化剂，显示出比参考抑制剂芦丁更好的糖化抑制活性（IC50 值 209.87±0.37–231.70±6.71 vs. 294.5±1.5 μm）。在植物毒性试验中，11 种缩氨基硫脲 5a-d、5g、5h、5j-l、5n,o 是有活性的，表明对 L. 的生长有 5-100% 的抑制作用。aequinocitalis 在最高测试浓度（1000 或 500 微克/毫升）。在盐水虾