1-[(4-hydroxyphenyl)methylidene]-4-phenyl-3-thiosemicarbazide | 76572-74-2

• 分子结构分类: 有机化合物 - 苯类化合物 - 酚类
• 英文名称: 1-[(4-hydroxyphenyl)methylidene]-4-phenyl-3-thiosemicarbazide
• 英文别名: 3-[(4-hydroxyphenyl)methylidene]amino-1-phenylthiourea；4-hydroxy-benzaldehyde 4-phenyl-thiosemicarbazone；4-hydroxy-benzaldehyde-(4-phenyl thiosemicarbazone)；4-Hydroxy-benzaldehyd-(4-phenyl-thiosemicarbazon)；4-Phenyl-1-(4-oxy-benzal)-thiosemicarbazid；4-Hydroxy-benzaldehyd-<4-phenyl-thiosemicarbazon>；1-[(4-Hydroxyphenyl)methylideneamino]-3-phenylthiourea
• CAS: 76572-74-2
• 化学式: C₁₄H₁₃N₃OS
• 分子量: 271.343
• InChiKey: IIKOSSZBVGWABG-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  19
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  88.7
• 氢给体数：
  3
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  马来酸酐 、 1-[(4-hydroxyphenyl)methylidene]-4-phenyl-3-thiosemicarbazide 在 溶剂黄146 作用下， 反应 2.0h， 以77%的产率得到[2-{[(4-hydroxyphenyl)methylidene]hydrazinylidene}-4-oxo-3-phenyl-1,3-thiazolidin-5-yl]acetic acid
  参考文献：
  名称：

  新型 Thiazolidin-4-one 衍生物的合成及体外抗弓形虫活性

  摘要：

  近期关于噻唑烷-4-酮生物活性的发现，并考虑到治疗弓形体病的有效药物缺乏、副作用众多，以及寄生虫耐药性问题促使我们寻找新的药物. 我们通过4-取代氨基脲与羟基苯甲醛之间的两步反应，然后用溴乙酸乙酯处理，设计并合成了一系列新的噻唑啉-4-one衍生物；马来酸酐和乙炔二羧酸二甲酯得到目标化合物。thiazolidin-4-one 衍生物用于评估体外弓形虫生长的抑制作用。所有活性 thiazolidine-4-one 衍生物（12 种化合物）均抑制 T. 体外弓形虫增殖比使用的参考药物磺胺嘧啶以及磺胺嘧啶+甲氧苄啶（重量比5：1）的协同作用要好得多。其中最活跃的衍生物 94 和 95 显示出比磺胺嘧啶更好约 392 倍和比磺胺嘧啶和甲氧苄啶更好 18 倍的增殖抑制作用。所有针对弓形虫的活性化合物（82-88 和 91-95）代表的值从 1.75 到 15.86 (CC30/IC50) 低于无细胞毒性值

  DOI：

  10.3390/molecules24173029
• 作为产物：
  描述：

  硫代异氰酸苯酯 在 甲醇 、 一水合肼 作用下， 以 四氢呋喃 、 甲醇 为溶剂， 反应 1.0h， 生成 1-[(4-hydroxyphenyl)methylidene]-4-phenyl-3-thiosemicarbazide
  参考文献：
  名称：

  缩氨基硫脲基 Ni(II) 复合物的细胞毒性行为和 DNA/BSA 结合活性：生物物理、分子对接和 DFT 研究

  摘要：

  双齿配体缩氨基硫脲 (H 3L) 及其 Ni(II) 络合物被合成并通过单晶 X 射线衍射和各种光谱方法进行了表征。Ni(II) 络合物在镍离子周围呈现出几乎正方形的平面几何形状，由两个配体通过 N 和 S 供体中心配位。该配合物单晶的重要结构特征是[空间群：P-1；a = 11.0594(9) Ǻ; b = 12.2339(9) Ǻ; c = 14.8835(9) Ǻ; α = 110.857(6); β = 91.029(6) 和 γ = 108.710(7)]。已执行 DFT/TD-DFT 模拟以确定 HOMO-LUMO 能量、电子光谱数据、最小能量优化结构，并使用 B3LYP 理论水平计算化合物的反应性描述符。基于理论研究的DFT和NBO分析有助于分别定位络合物中配体的MEP表面和键合模式。不同的反应性描述符建立了它们的反应性和分子的生物分子亲和力之间的关联。化合物与 DNA 和 BSA

  DOI：

  10.1016/j.molliq.2023.121921

文献信息

• Inhibition of Xanthine Oxidase by Thiosemicarbazones, Hydrazones and Dithiocarbazates Derived from Hydroxy-Substituted Benzaldehydes
  作者：Maria Leigh、Daniel J. Raines、Carmen E. Castillo、Anne K. Duhme-Klair

  DOI：10.1002/cmdc.201100054

  日期：2011.6.6

  and tested for XOR inhibitory activity. Hydroxy substitution in the para‐position of the benzaldehyde component was found to confer high inhibitory activities. Acyl hydrazones were generally less potent than thiocarbonyl‐containing Schiff bases. Within the thiosemicarbazone series, chloro and cyano substituents in the para‐position of the thiosemicarbazide unit increased activities further, up to potencies

  非嘌呤黄嘌呤氧化还原酶（XOR）抑制剂是嘌呤类似物别嘌呤醇的重要替代品，别嘌呤醇仍然是治疗与血液中尿酸水平升高有关的疾病的最广泛使用的药物。通过将单，二和三羟基苯甲醛与芳族硫代氨基脲，芳基酰肼和二硫代氨基甲酸酯缩合，合成了三组结构相关的席夫碱，表征并测试了其XOR抑制活性。发现苯甲醛成分对位的羟基取代具有较高的抑制活性。酰基的效力一般不如含硫羰基的席夫碱。内的缩氨基硫脲系列，氯和氰基的取代基对在相同的分析条件下测得，硫代氨基脲单元的位置进一步提高了活性，其效力比基准别嘌呤醇的效力高约四倍。为了说明席夫碱直接与酶活性位点上的钼中心结合的潜力，将每个抑制剂系列的一个代表性实例（H 2 L）与一个顺式-二氧钼（VI）单元配位。 ，以及生成的络合物[MoO 2（L）MeOH]的结构表征。然而，随后的稳态动力学研究表明，混合型抑制作用类似于已知在远离Mo中心的酶的底物进入通道内结合的抑制剂所观察到的
• One-pot two-step facile synthesis of 2,3,4,5-tetra substituted dihydrooxazoles and their antimicrobial activity
  作者：Shailendra Tiwari、Poonam Pathak、Kamal Pratap Singh、Ram Sagar

  DOI：10.1016/j.bmcl.2017.06.062

  日期：2017.8

  New 2,3,4,5-tetra substituted dihydrooxazoles derivatives were efficiently synthesized starting from benzaldehyde, aryl thiosemicarbazide and benzoin using designed synthetic route. Newly synthesized 2,3,4,5-tetra substituted dihydrooxazole derivatives were screened for their antibacterial and antifungal activities against different strains of pathogenic bacteria and fungi. The minimum inhibitory concentration

  使用设计的合成路线，从苯甲醛，芳基硫代氨基脲和苯偶姻开始有效地合成了新的2,3,4,5-四取代的二氢恶唑衍生物。筛选了新合成的2,3,4,5-四取代的二氢恶唑衍生物对不同菌株的致病细菌和真菌的抗菌和抗真菌活性。使用阳性和阴性对照确定测试化合物的最小抑菌浓度（MIC），最小杀菌浓度（MBC）和最小杀菌浓度（MFC）。化合物4b，4d，4f，4i，4k和4m具有良好的抗菌活性，而化合物4e，4g，4h，4j，4l和4n显示出更好的抗真菌活性。
• Negotiating the Public Sphere through Private Correspondence: A Woman’s Letters of Liberty in Eighteenth-Century Germany
  作者：Melanie Archangeli

  DOI：10.1111/1468-0483.00178

  日期：2000.10

  The pivotal role played by letters in eighteenth‐century German literary, cultural and everyday life has long been recognised. In contrast to earlier times, many of the letters written in the eighteenth century were composed by women, and their correspondence provides modern scholars with a rich source of information abour the process of communication in the intimate, private and public spheres. The linited correspondence of Charlotte von Hezel, the first woman in Germany to edit a periodical under her own name, is of particular interest because it offers one of the few examaples of a woman corresponding with men for professional, not personal reasons. In addition, Hezel, not her male correspondents, represents the voice of authority within the area of activity being discussed: the publication of her magazine. Hezel’s self‐assurance is remarkable for a German woman of the time, and her letters demonstrate a liberating process of communication that allowed individuals hingered by gender, educational background or social status to debate contemporary issues and exchange serviced as they negotiated their entry into the public sphere.
• Phenolic thio- and selenosemicarbazones as multi-target drugs
  作者：Verónica Calcatierra、Óscar López、José G. Fernández-Bolaños、Gabriela B. Plata、José M. Padrón

  DOI：10.1016/j.ejmech.2015.02.037

  日期：2015.4

  A series of isosteric phenolic thio- and selenosemicarbazones have been obtained by condensation of naturally-occurring phenolic aldehydes and thio(seleno)semicarbazides. Title compounds were designed as potential multi-target drugs, and a series of structure-activity relationships could be established upon their in vitro assays: antioxidant activity, alpha-glucosidase inhibition and antiproliferative activity against six human tumor cell lines: A549 (non-small cell lung), HBL-100 (breast), HeLa (cervix), SW1573 (non-small cell lung), T-47D (breast) and WiDr (colon). For the antiradical activity, selenium atom and 2 or 3 phenolic hydroxyl groups proved to be essential motifs; remarkably, the compound with the most potent activity, with a trihydroxyphenyl scaffold (EC50 = 4.87 +/- 1.57 mu M) was found to be stronger than natural hydroxytyrosol, a potent antioxidant present in olive oil (EC50 = 13.80 +/- 1.41 mu M). Furthermore, one of the thiosemicarbazones was found to be a strong non-competitive inhibitor of alpha-glucosidase (K-i = 9.6 +/- 1.6 mu M), with an 8-fold increase in activity compared to acarbose (K-i = 77.9 +/- 11.4 mu M), marketed for the treatment of type-2 diabetes. Most of the synthesized compounds also exhibited relevant antiproliferative activities; in particular, seleno derivatives showed GI(50) values lower than 6.0 mu M for all the tested cell lines; N-naphthyl mono- and dihydroxylated derivatives behaved as more potent antiproliferative agents than 5-fluorouracil or cisplatin. (C) 2015 Elsevier Masson SAS. All rights reserved.
• Synthesis and Ribonucleotide reductase inhibitory activity of thiosemicarbazones
  作者：Kesavan Krishnan、Kumari Prathiba、Venkatesan Jayaprakash、Arijit Basu、Nibha Mishra、Bingsen Zhou、Shuya Hu、Yun Yen

  DOI：10.1016/j.bmcl.2008.09.097

  日期：2008.12

  Ribonucleotide reductase (RR) is an important therapeutic target for anticancer drugs. The structure of human RR features a 1: 1 complex of two homodimeric subunits, hRRM1 and hRRM2. Prokaryotically expressed and highly purified recombinant human RR subunits, hRRM1 and hRRM2, were used for holoenzyme-based [(3)H] CDP reduction in vitro assay. Ten new thiosemicarbazones (7-16) were synthesized and screened for their RR inhibitory activity. Two thiosemicarbazones derived from p-hydroxy benzaldehyde (9 and 10) were found to be active but less potent than the standard, Hydroxyurea (HU). Guided by the activity of compounds 9 and 10, 11 new thiosemicarbazones (17-27) derived from p-hydroxy benzaldehyde were prepared and screened for their RR inhibitory activity. All the 11 compounds were more potent than HU. (C) 2008 Elsevier Ltd. All rights reserved.