2-hydroxy-1-naphthaldehyde thiosemicarbazone | 7410-40-4

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: 2-hydroxy-1-naphthaldehyde thiosemicarbazone
• 英文别名: 2-Hydroxy-[1]naphthaldehyd-thiosemicarbazon；[(2-hydroxynaphthalen-1-yl)methylideneamino]thiourea
• CAS: 7410-40-4
• 化学式: C₁₂H₁₁N₃OS
• mdl: MFCD00434164
• 分子量: 245.305
• InChiKey: INVDVNVYLCEPSF-UHFFFAOYSA-N

物化性质

• 熔点：
  280 °C (decomp)(Solv: acetic acid (64-19-7))
• 沸点：
  463.0±47.0 °C(Predicted)
• 密度：
  1.35±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  17
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  103
• 氢给体数：
  3
• 氢受体数：
  3

安全信息

• 海关编码：
  2930909090

反应信息

• 作为反应物：
  描述：

  2-hydroxy-1-naphthaldehyde thiosemicarbazone 在 lithium chloride 作用下， 以 乙醇 为溶剂， 生成
  参考文献：
  名称：

  Novel molecular discovery of promising amidine-based thiazole analogues as potent dual Matrix Metalloproteinase-2 and 9 inhibitors: Anticancer activity data with prominent cell cycle arrest and DNA fragmentation analysis effects

  摘要：

  Thiazole derivatives are known to possess various biological activities such as antiparasitic, antifungal, anti-microbial and antiproliferative activities. Matrix metalloproteinases (MMPs) are important protease target in-volved in tumor progression including angiogenesis, tissue invasion, and migration. Therefore, MMPs have also been reported as potential diagnostic and prognostic biomarkers in many types of cancer. Herein, new aryl thiazoles were synthesized and evaluated for their anticancer effects on a panel of cancer cell lines including the invasive MDA-MB-231 line. Some of these compounds showed IC50 values in the submicromolar range in anti -proliferative assays. In order to examine the relationship between their anticancer activity and MMPs targets, the compounds were evaluated for their inhibitory effects on MMP-2 and 9. That data obtained revealed that most of these compounds were potent dual MMP-2/9 inhibitors at nanomolar concentrations. Among these, 2-(1-(2-(2-((E)-4-iodobenzylidene)hydrazineyl)-4-methylthiazol-5-yl)ethylidene)hydrazine-1-carboximidamide (4a) was the most potent non-selective dual MMP-2/9 inhibitor with inhibitory concentrations of 56 and 38 nM re-spectively. When compound 4a was tested in an MDA-MB-231, HCT-116, MCF-7 model, it effectively inhibited tumor growth, strongly induced cancer cell apoptosis, inhibit cell migration, and suppressed cell cycle pro-gression leading to DNA fragmentation. Taken together, the results of our studies indicate that the newly dis-covered thiazole-based MMP-2/9 inhibitors have significant potential for anticancer treatment.

  DOI：

  10.1016/j.bioorg.2020.103992
• 作为产物：
  描述：

  氨基硫脲 、 2-羟基-1-萘甲醛 在 溶剂黄146 作用下， 以 甲醇 为溶剂， 反应 4.0h， 以82.4%的产率得到2-hydroxy-1-naphthaldehyde thiosemicarbazone
  参考文献：
  名称：

  基于人血清白蛋白载体IIA亚域的N-供体残基开发抗癌铁前药。

  摘要：

  为了提高三价铁（Fe）抗癌药的选择性，递送和活性，我们基于人血清白蛋白（HSA）载体IIA子域的N供体残基设计了前药。我们合成了由2-羟基-1-萘醛缩氨基硫脲（派生6的Fe（III）化合物7 - 12）。HSA复杂结构表明，Fe化合物与HSA IIA子域中的疏水腔结合。HSA的Lys199和His242取代了Fe化合物的两个Cl原子，并与Fe 3+配位。体内数据显示，化合物12和HSA- 12复合物抑制肝肿瘤的生长，而HSA- 12该复合物比单独的化合物12具有更强的靶向能力和治疗功效。另外，我们的结果表明，化合物12和HSA - 12复合物可能通过几种机制诱导Bel-7402细胞死亡。

  DOI：

  10.1021/acs.jmedchem.6b00509

文献信息

• Vanadium(IV and V) Complexes ContainingSNO (Dithiocarbonylhydrazone; Thiosemicarbazone) Donor Sets
  作者：Dongren Wang、Martin Ebel、Carola Schulzke、Cerstin Grüning、Saroj K. S. Hazari、Dieter Rehder

  DOI：10.1002/1099-0682(200104)2001:4<935::aid-ejic935>3.0.co;2-j

  日期：2001.4

  signals, two of which are due to two diastereomers. The EPR spectra of 3 and 4 in THF reveal the presence of octahedral species in solution. The crystal and molecular structures of complexes 3a·OCMe2, 5a, and 5b have been obtained, revealing basically a tetragonal pyramid, and coordination of the sulfur function in the thiocarbonyl (3) or enethiolate mode (5). The relevance of the compounds to bioinorganic

  VO2+ 复合物 [VOCl(ONS)] (3) 和 [VO(ONS)'] (4)，以及 VO3+ 复合物 [VO(OEt)(ONS)'] (5) ONS = (R)-水杨醛缩氨基硫脲(1-) R = 5,6-C4H4 (3a) 或 3-OMe (3b)；(ONS)' = (R)-水杨醛[benzylmercaptothiocarbonylhydrazonate(2−)], R = H, (4a/5a) 或 3-OMe (4b/5b)} 已制备并通过 IR、EPR、1H-、和 51V-NMR 光谱。在 (S)-sBuOH 中，4a 转化为 [VO(S)-OsBu}(ONS)'] (5c) 和 [VO(OH)(ONS)']（或其缩合产物）。5c 的溶液显示三个 51V NMR 信号，其中两个是由于两种非对映异构体。THF 中 3 和 4 的 EPR 光谱揭示了溶液中存在八面体物质。已获得
• In vitro antiproliferative activity of palladium(<scp>ii</scp>) thiosemicarbazone complexes and the corresponding functionalized chitosan coated magnetite nanoparticles
  作者：Wilfredo Hernández、Abraham. J. Vaisberg、Mabel Tobar、Melisa Álvarez、Jorge Manzur、Yuri Echevarría、Evgenia Spodine

  DOI：10.1039/c5nj02429c

  日期：——

  Magnetite functionalized nanoparticles with Pd(L³)₂ and Pd(L⁴)₂ show antiproliferative activity against DU-145 and HuTu80; Pd(L²)₂ is found to be a promising pharmacological agent.

  磁铁矿功能化纳米颗粒与Pd(L³)₂和Pd(L⁴)₂对DU-145和HuTu80显示抗增殖活性；Pd(L²)₂被发现是一种有前景的药理试剂。
• Dual anion colorimetric and fluorometric sensing of arsenite and cyanide ions
  作者：Neetu Yadav、Ashok Kumar Singh

  DOI：10.1039/c6ra19781g

  日期：——

  appended probe, 2-((2-hydroxynaphthalen-1-yl)methylene)hydrazine carbothioamide, was synthesized and found to recognize AsO2− and CN− ions with turn-on emission fluorescence over different anions in a DMF : H2O (HEPES buffer, pH = 7.2) (9 : 1, v/v solution) medium. The probe was characterized using different techniques including NMR, IR, CHNS, UV-visible and ESI mass spectroscopy. This probe shows colorimetric

  甲萘所附探头，2 - （（2-羟基萘-1-基）亚甲基）肼硫代甲酰胺，合成并发现识别ASO 2 -和CN -与接通发射荧光随在DMF不同阴离子的离子：H 2O（HEPES缓冲液，pH = 7.2）（9：1，v / v溶液）培养基。使用不同的技术（包括NMR，IR，CHNS，UV可见光谱和ESI质谱）对探针进行表征。该探针显示出比色变化，以及其他阴离子中亚砷酸盐和氰化物离子的荧光发射增强。根据紫外线可见光谱，由乔布氏图计算出分别具有砷和氰化物离子的探针的1：1和1：2的化学计量比。使用B–H（Benesi–Hildebrand）曲线建立结合常数，砷，砷和氰化物的阴离子浓度分别为3.1×10 5和1.9×10 6。使用发射光谱，亚砷酸盐和氰化物离子的检出限（LOD）分别为66 nM和77 nM。探针的结合亲和力使用NMR，DFT优化，ESI质谱，电化学行为和光学研究确定带有两种阴离子的L。该探针
• Synthesis and antimicrobial properties of some new thiazolyl coumarin derivatives
  作者：Afsheen Arshad、Hasnah Osman、Mark C. Bagley、Chan Kit Lam、Suriyati Mohamad、Anis Safirah Mohd Zahariluddin

  DOI：10.1016/j.ejmech.2011.05.044

  日期：2011.9

  Two novel series of hydrazinyl thiazolyl coumarin derivatives have been synthesized and fully characterized by IR, 1H NMR, 13C NMR, elemental analysis and mass spectral data. The structures of some compounds were further confirmed by X-ray crystallography. All of these derivatives, 10a–d and 15a–h, were screened in vitro for antimicrobial activity against various bacteria species including Mycobacterium

  已经合成了两个新颖的肼基噻唑基香豆素衍生物系列，并通过IR，1 H NMR，13 C NMR，元素分析和质谱数据进行了充分表征。X射线晶体学进一步证实了某些化合物的结构。在体外筛选了所有这些衍生物10a – d和15a – h对各种细菌（包括结核分枝杆菌和白色念珠菌）的抗菌活性。化合物10c，10d和15e 对所有测试的微生物菌株表现出非常好的活性。
• Synthesis, antibacterial and antifungal activity of some new thiazolylhydrazone derivatives containing 3-substituted cyclobutane ring
  作者：Alaaddin Cukurovali、İbrahim Yilmaz、Seher Gur、Cavit Kazaz

  DOI：10.1016/j.ejmech.2005.01.013

  日期：2006.2

  A series of Schiff bases, combining 2,4-disubstituted thiazole and cyclobutane rings, and hydrazone moieties in the same molecule, was synthesized, characterized and evaluated for screening antibacterial and antifungal activities on microorganisms, respectively, on four bacteria and Candida tropicalis. The structures of original compounds were confirmed by analytical and spectroscopic (FT-IR, (1)H

  合成，组合并表征了一系列席夫碱，这些席夫碱将2,4-二取代的噻唑和环丁烷环以及rings部分结合在同一分子中，并分别针对四种细菌和热带念珠菌进行了筛选，以筛选其对微生物的抗菌和抗真菌活性。原始化合物的结构通过分析和光谱法（FT-IR，（1）H NMR和（13）C NMR）方法以及元素分析得到确认。化合物的抗菌和抗真菌活性以及MIC值都有报道。在测试的化合物中，提供MIC值为16微克ml（-1）的最有效化合物是仅对付热带假丝酵母和枯草芽孢杆菌2个，对付枯草芽孢杆菌3个。