3,4,5-三甲氧基苯甲酰异硫氰 | 6939-63-5

• 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: 3,4,5-三甲氧基苯甲酰异硫氰
• 英文名称: 3,4,5-Trimethoxy-benzoylisothiocyanat
• 英文别名: 3,4,5-Trimethoxybenzoyl isothiocyanate
• CAS: 6939-63-5
• 化学式: C₁₁H₁₁NO₄S
• mdl: MFCD00046811
• 分子量: 253.279
• InChiKey: SRJJUWPSSFADES-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  17
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.272
• 拓扑面积：
  89.2
• 氢给体数：
  0
• 氢受体数：
  5

安全信息

• 海关编码：
  2930909090

反应信息

• 作为反应物：
  描述：

  3,4,5-三甲氧基苯甲酰异硫氰 在 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 、 六甲基二硅氮烷 作用下， 以 丙酮 、 乙腈 为溶剂， 反应 6.0h， 生成 MRT-83
  参考文献：
  名称：

  Acylthiourea, Acylurea, and Acylguanidine Derivatives with Potent Hedgehog Inhibiting Activity

  摘要：

  The Smoothened (Smo) receptor is the major transducer of the Hedgehog (Hh) signaling pathway. On the basis of the structure of the acylthiourea Smo antagonist (MRT-10), a number of different series of analogous compounds were prepared by ligand-based structural optimization. The acylthioureas, originally identified as actives, were converted into the corresponding acylureas or acylguanidines. In each series, similar structural trends delivered potent compounds with IC50 values in the nanomolar range with respect to the inhibition of the Hh signaling pathway in various cell-based assays and of BODIPY-cyclopamine binding to human Smo. The similarity of their biological activities, in spite of discrete structural differences, may reveal the existence of hydrogen-bonding interactions between the ligands and the receptor pocket. Biological potency of compounds 61, 72, and 86 (MRT-83) were comparable to those of the clinical candidate GDC-0449. These findings suggest that these original molecules will help delineate Smo and Hh functions and can be developed as potential anticancer agents.

  DOI：

  10.1021/jm2013369
• 作为产物：
  描述：

  3,4,5-三甲氧基苯甲酰氯 在 potassium thioacyanate 作用下， 以 乙腈 为溶剂， 反应 0.25h， 以96%的产率得到3,4,5-三甲氧基苯甲酰异硫氰
  参考文献：
  名称：

  Benzimidazole derivatives and their use as gnrh antagonists

  摘要：

  本申请的主题是新的苯并咪唑衍生物，其化学式为其中A、Y、R1、R2、R3和R4代表不同的变量基团。这些产物具有GnRH（促性腺激素释放激素）的拮抗活性。该发明还涉及含有上述产物的药物组合物以及它们用于制备药物的用途。

  公开号：

  US20050049290A1

文献信息

• Design, Synthesis, and Insecticidal Activity of Novel Doramectin Derivatives Containing Acylurea and Acylthiourea Based on Hydrogen Bonding
  作者：Qi Zhang、Yao Cheng、Cheng Zheng、Ping Bai、Jian Yang、Xiaoxia Lu

  DOI：10.1021/acs.jafc.0c00230

  日期：2020.5.27

  investigation on the insecticidal activities of several doramectin derivatives preliminarily revealed that the presence of hydrogen bonds at the C4″ position of the molecule with target protein γ-aminobutyric acid (GABA) receptor was crucial for retaining high insecticidal activity. As a continuation of our research work on the development of new insecticides, two series of novel acylurea and acylthiourea

  我们最近对几种多拉菌素衍生物的杀虫活性的研究初步表明，在具有目标蛋白γ-氨基丁酸（GABA）受体的分子的C4''位置存在氢键对于保持高杀虫活性至关重要。作为我们对新型杀虫剂开发的研究工作的继续，设计并合成了两个系列的新型酰基脲和酰基硫脲多拉菌素衍生物。生物测定结果表明，在我们的实验室中，新合成的化合物（5o，5t和6t）对小菜蛾，东方粘虫和玉米bore的杀虫活性高于对照化合物doramectin，市售阿维菌素，敌百虫和铅化合物3g。特别，化合物5t被确定为最有前景的小菜蛾杀虫剂，在低浓度12.50 mg / L时最终死亡率为80.00％，其效力比母体多拉菌素高约7.75倍（LC50值为48.1547 mg / L ），效力比市售阿维菌素（LC50值为40.5507 mg / L）高6.52倍，效力比化合物3g（LC50值为24.7742 mg / L）高3.98倍。此外，分子对接模拟显示化合物5t（2
• Synthesis, characterization of some new 1-aroyl-3-(4-aminosulfonylphenyl)thioureas and crystal structure of 1-(3,4,5-trimethoxybenzoyl)- 3-(4-aminosulfonylphenyl)thiourea
  作者：Aamer Saeed、Amara Mumtaz、H. Ishida

  DOI：10.1080/17415993.2010.541461

  日期：2011.2.1

  A small library of novel 1-aroyl-3-(4-aminosulfonylphenyl)thiourea derivatives was synthesized by the reaction of sulfanilamide with substituted aroyl isothiocyanates in dry acetonitrile. The scope of the reaction was indicated by the synthesis of 1-undecanoyl-3-(4-aminosulfonylphenyl)thiourea, an acyl derivative involving alkanoyl isothiocyanate. All the compounds have been characterized by analytical

  通过磺胺与取代的芳酰基异硫氰酸酯在干燥乙腈中的反应，合成了一个小型的新型 1-芳酰基-3-(4-氨基磺酰基苯基) 硫脲衍生物。反应的范围通过合成 1-undecanoyl-3-(4-aminosulfonylphenyl)thiourea，一种涉及烷酰基异硫氰酸酯的酰基衍生物来表明。所有化合物都通过分析和光谱方法进行了表征，在一种情况下，通过单晶 X 射线衍射数据进行了表征。
• Biological Evaluation of Halogenated Thioureas as Cholinesterases Inhibitors Against Alzheimer’s Disease & Molecular Modeling Studies
  作者：Jamshed Iqbal、Sumera Zaib、Aamer Saeed、Muhammad Muddassar

  DOI：10.2174/1570180812666141201222247

  日期：2015.5.7

  Acetylcholinesterase (AChE) and butyrylcholinesterase (BChE) inhibition is thought to be an encouraging approach towards the therapy of Alzheimer’s disease (AD). The current paper targets to give a concise information of mono and dihalo- substituted thioureas similarity with anti-AD potential. The present results represent evaluation of cholinesterase inhibitory potential for halogenated thioureas derivatives. Compound 1t was constituted to be highly potent inhibitor with Ki value 0.12 ± 0.05 µM against AChE, while 1b was most the active inhibitor for BChE with Ki value of 0.03 ± 0.001 µM. Molecular docking simulations were performed using the homology models of both cholinesterases in order to explore the plausible binding modes of synthesized compounds.

  乙酰胆碱酯酶（AChE）和丁酰胆碱酯酶（BChE）的抑制被认为是治疗阿尔茨海默病（AD）的一个有前景的方法。本文旨在简要介绍单卤和二卤取代的硫脲与抗阿尔茨海默潜力的相似性。目前的结果展示了卤代硫脲衍生物的胆碱酯酶抑制潜力评估。化合物1t被确定为一种高效抑制剂，对AChE的Ki值为0.12 ± 0.05 µM，而1b是对BChE最活跃的抑制剂，Ki值为0.03 ± 0.001 µM。利用胆碱酯酶的同源模型进行了分子对接模拟，以探讨合成化合物的可能结合模式。
• Synthesis, characterization and antimicrobial activity of some new 1-(fluorobenzoyl)-3-(fluorophenyl)thioureas
  作者：Aamer Saeed、Uzma Shaheen、A. Hameed、S.Z. Haider Naqvi

  DOI：10.1016/j.jfluchem.2009.09.003

  日期：2009.11

  Synthesis of a variety of new 1-(isomeric fluorobenzoyl)-3-(isomeric fluorophenyl)thioureas (1a–t) was accomplished in two steps. The synthetic route involves the reaction of equimolar quantities of isomeric fluorobenzoyl chlorides with potassium thiocyanate in anhydrous acetone to afford the corresponding isothiocyantes in situ, followed by treatment with equimolar quantities of isomeric fluoroanilines

  各种新的1-（异构氟苯甲酰基）-3-（异构氟苯基）硫脲（1a – t）的合成分两个步骤完成。合成路线包括等摩尔量的氟代苯甲酰氯异构体与无水丙酮中的硫氰酸钾反应，原位提供相应的异硫氰酸酯，然后用等摩尔量的氟苯胺类异构体处理。所有合成的化合物（1A -吨）筛选了在体外使用革兰氏阳性菌的抗菌活性（金黄色葡萄球菌，枯草芽孢杆菌的革兰氏阴性菌）和（大肠杆菌，铜绿假单胞菌（Pseudomonas aureginosa）。还确定了活性最高的化合物的最小抑菌浓度（MIC）。体外抗真菌活性也针对五个真菌物种（确定米根霉，土曲霉，尖镰孢，黑曲霉，烟曲霉）。通常，化合物的抗真菌活性优于其抗菌活性。
• New Substituted Thiazol-2-ylidene-benzamides and Their Reaction with 1-Aza-2-azoniaallene Salts. Synthesis and anti-HIV Activity
  作者：Aamer Saeed、Najim A. Al-Masoudi、Amjed A. Ahmed、Christophe Pannecouque

  DOI：10.1515/znb-2011-0512

  日期：2011.5.1

  A series of N-(3-(substituted-alkyl- or halophenyl)-4-methylthiazol-2(3H)-ylidene)-substituted alkyl- or halo-benzamides 21 - 40 were prepared by base-catalyzed cyclization of the corresponding 1-(substituted-alkyl- or halo-benzoyl)-3-(substituted-halophenyl)thioureas 1 - 20. Substituted pyrazolo[ 4,3-d]thiazol-5(6aH)-ylidene)benzamides 45a - d were synthesized by cycloaddition of compound 45 with the reactive cumulene intermediates 42a - d. All compounds were evaluated for their antiviral activity against the replication of HIV^-1 and HIV-2 in MT-4. Compounds 35 and 39 showed an IC₅₀ of 2.02 μgmL⁻¹ and 0.40 μgmL⁻¹ against the HIV-2 strain ROD with CC₅₀ of ≥ 104.00 μgmL⁻¹ and > 125.00 μgmL⁻¹, respectively, resulting in a selectivity index of ≥ 52 and > 313. Based on the chemical structure of compounds 35 and 39, these molecules can be proposed to act as NNRTIs. However, it is exceptional to observe an antiretroviral activity that is limited to HIV-2

  一系列N-(3-(取代烷基或卤代苯基)-4-甲基噻唑-2(3H)-基)-取代烷基或卤代苯甲酰胺21-40通过对应的1-(取代烷基或卤代苯甲酰)-3-(取代卤代苯基)硫脲1-20的碱催化环化反应制备。通过将化合物45与反应性累烯中间体42a-d进行环加成反应合成了取代吡唑并[4,3-d]噻唑-5(6aH)-基)苯甲酰胺45a-d。评估所有化合物对MT-4中HIV-1和HIV-2的复制的抗病毒活性。化合物35和39对HIV-2 ROD株显示了IC50值分别为2.02 μg/mL和0.40 μg/mL，CC50值分别为≥104.00 μg/mL和>125.00 μg/mL，因此选择性指数分别为≥52和>313。根据化合物35和39的化学结构，这些分子可能作为非核苷逆转录酶抑制剂。然而，观察到限于HIV-2的抗逆转录病毒活性是异常的。