2-羟基-1-萘甲醛缩氨基硫脲 | 7410-40-4

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 中文名称: 2-羟基-1-萘甲醛缩氨基硫脲
• 英文名称: 2-hydroxy-1-naphthylcarbaldehyde (E)-thiosemicarbazone
• 英文别名: 2-hydroxynaphthalenecarbaldehyde thiosemicarbazone；2-hydroxynaphthaldehyde thiosemicarbazone；2-hydroxy-1-naphthaldehyde thiosemicarbazone；(E)-2-((2-hydroxynaphthalen-1-yl)methylene)hydrazinecarbothioamide；2-hydroxynaphthalene-1-carbaldehyde thiosemicarbazone；2-[(2-Hydroxy-1-naphthyl)methylidene]hydrazine-1-carbothioamide；hntsc；2-Hydroxy-1-naphthaldehyde thiosemicarbazone；[(E)-(2-hydroxynaphthalen-1-yl)methylideneamino]thiourea
• CAS: 7410-40-4
• 化学式: C₁₂H₁₁N₃OS
• 分子量: 245.305
• InChiKey: INVDVNVYLCEPSF-VGOFMYFVSA-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)
• 溶解度：
  2.5 [ug/mL]

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-羟基-1-萘甲醛缩氨基硫脲 在 Et₃N 作用下， 以 甲醇 、 乙醇 为溶剂， 生成 Pt(C10H6(O)CHNNCSNH2)(triphenylphosphine)
  参考文献：
  名称：

  Synthesis, structure and spectroscopic properties of some thiosemicarbazone complexes of platinum

  摘要：

  Reaction of salicyldehyde thiosemicarbazone (H2L1), 2-hydroxyacetophenone thiosemicarbazone (H2L2) and 2-hydroxynapthaidehyde thiosemicarbazone (H2L3) (general abbreviation H2L, where H-2 stands for the two dissociable protons, one phenolic proton and one hydrazinic proton) with K-2[PtCl4] afforded a family of polymeric complexes of type [{Pt(L)}(n)] Reaction of the polymeric species with two monodentate ligands (D), viz. triphenylphosphine (PPh3) and 4-picoline (pic), yielded complexes of the type [Pt(L)(D)]. These mixed-ligand complexes were also obtained from the reaction of the thiosenticarbazones with [Pt(PPh3)(2)Cl-2] and [Pt(pic)(2)Cl-2]. The crystal structure of [Pt(MAL 2)] has been determined. The thiosernicarbazone ligands are coordinated, via dissociation of the two protons, as dianionic tridentate O,N,S-donors. The [Pt(L)(D)] complexes show characteristic H-1 NMR spectra and intense absorptions in the visible and ultraviolet region. They also fluoresce in the visible region at ambient temperature. (C) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.poly.2007.01.048
• 作为产物：
  描述：

  氨基硫脲 、 2-羟基-1-萘甲醛 以 甲醇 为溶剂， 反应 2.0h， 以52%的产率得到2-羟基-1-萘甲醛缩氨基硫脲
  参考文献：
  名称：

  作为潜在的抗肿瘤药的新型硫半脲类衍生物：合成，理化和结构性质，DNA相互作用和抗增殖活性。

  摘要：

  该论文描述了几种新型硫代半碳酰胺衍生物的合成。此外，4-二乙基氨基-水杨醛4-苯基硫代半脲的晶体和分子结构揭示了共轭芳族体系的平面性，这暗示了通过嵌入特别是对于本文研究的萘衍生物而言，DNA结合的可能性。但是，这里提出的DNA结合研究排除了这种作用方式。将新型衍生物的理化和结构性质与先前研究的类似物（作为参考化合物）进行比较，揭示出明显的差异。此外，新的硫代半脲衍生物（1、2和5-8）在五个肿瘤细胞系上的抗增殖活性明显高于参考化合物3和4，这支持了它们作为潜在抗肿瘤剂的进一步研究。

  DOI：

  10.1016/j.bmc.2008.03.006

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 antioxidant, antiinflammatory and in silico molecular docking studies of thiosemicarbazones
  作者：G.R. Subhashree、J. Haribabu、S. Saranya、P. Yuvaraj、D. Anantha Krishnan、R. Karvembu、D. Gayathri

  DOI：10.1016/j.molstruc.2017.05.054

  日期：2017.10

  1-naphthaldehyde and (un)substituted thiosemicarbazides with the view to ascertain their biological properties brought about by the change in substitution at N-terminal position of the thiosemicarbazide derivatives. The compounds were fully characterized by elemental analyses, and various spectroscopic techniques (UV–Visible, FT-IR, NMR and mass). The solid-state structure of three compounds (1, 2

  摘要 5-甲氧基水杨醛/2-羟基-1-萘醛与(un)反应得到了一系列5-甲氧基水杨醛附加氨基硫脲(1-4)和2-羟基-1-萘醛附加氨基硫脲(5-8)。氨基硫脲衍生物的 N 末端位置的取代变化所带来的生物学特性。通过元素分析和各种光谱技术（紫外-可见光、红外光谱、核磁共振和质谱）对化合物进行了全面表征。三种化合物（1、2 和 7）的固态结构通过单晶 X 射线衍射法测定。化合物(1、2和7)采用具有P21/c(1和2)或C2/c(7)空间群的单斜晶系。分别通过体外 DPPH 和溶血试验分析了化合物 (1-8) 的抗氧化和非溶血活性。抗炎潜力通过体外 PLA2 抑制试验和计算机分子对接研究得到验证。体外和计算机研究揭示了缩氨基硫脲衍生物有希望的抗炎潜力。化合物 2、4、6、7 和 8 显示出显着的抗炎活性。
• Inhibitors of protein kinase for the treatment of disease
  申请人：——

  公开号：US20030187007A1

  公开（公告）日：2003-10-02

  The present invention is directed in part towards methods of modulating the function of protein kinases with phenol- and hydroxynaphthalene-based compounds. The methods incorporate cells that express a protein kinase. In addition, the invention describes methods of preventing and treating protein kinase-related abnormal conditions in organisms with a compound identified by the invention. Furthermore, the invention pertains to phenol- and hydroxynaphthalene-based compounds and pharmaceutical compositions comprising these compounds.

  本发明部分涉及使用基于酚和羟基萘的化合物调节蛋白激酶功能的方法。这些方法涉及表达蛋白激酶的细胞。此外，该发明描述了使用本发明鉴定的化合物预防和治疗生物体中与蛋白激酶相关的异常情况的方法。此外，该发明涉及基于酚和羟基萘的化合物以及包含这些化合物的药物组合物。
• Synthesis, structure, spectroscopic properties and cytotoxic effect of some thiosemicarbazone complexes of palladium
  作者：Sarmistha Halder、Shie-Ming Peng、Gene-Hsiang Lee、Tanmay Chatterjee、Asama Mukherjee、Sushanta Dutta、Utpal Sanyal、Samaresh Bhattacharya

  DOI：10.1039/b707448d

  日期：——

  Reaction of salicylaldehyde thiosemicarbazone (H2L1), 2-hydroxyacetophenone thiosemicarbazone (H2L2) and 2-hydroxynaphthaldehyde thiosemicarbazone (H2L3) (general abbreviation H2L, where H2 stands for the two dissociable protons, one phenolic proton and one hydrazinic proton) with Na2[PdCl4] affords a family of polymeric complexes of type [Pd(L)}n]. Reaction of the polymeric species with two monodentate ligands (D), viz. triphenylphosphine (PPh3) and 4-picoline (pic), has yielded complexes of type [Pd(L)(D)]. These mixed-ligand complexes have also been obtained from reaction of the thiosemicarbazones with [Pd(PPh3)2Cl2] and [Pd(pic)2Cl2]. Crystal structures of [Pd(L1)(PPh3)] and [Pd(L2)(pic)] have been determined. The [Pd(L)(D)] complexes show characteristic 1H NMR spectra and intense absorptions in the visible and ultraviolet region. They also fluoresce in the visible region at ambient temperature. In vitro cytotoxicity screenings of the complexes along with four human clinical drugsviz.cisplatin, BCNU, 5-fluorouracil (5-FU) and hydroxyurea have been carried out in two human tumor cell lines, namely promyelocytic leukemia HL-60 and histiocytic lymphoma U-937. [Pd(L2)(PPh3)] shows the lowest IC50 value and is found to be much more cytotoxic than the reference anticancer drugs in both the cell lines. An apoptosis study in HL-60 with [Pd(L2)(PPh3)] confirms that at 10 µM concentration it induces apoptosis to a greater extent than cisplatin and camptothecin.

  水杨醛缩氨基硫脲(H2L1)、2-羟基苯乙酮缩氨基硫脲(H2L2)和2-羟基萘醛缩氨基硫脲(H2L3)(通用缩写为H2L,其中H2代表两个可解离的质子,分别为酚羟基和肼基的质子)与Na2[PdCl4]反应生成了一类聚合物配合物[Pd(L)}n]。这类聚合物与两个单齿配体,例如三苯基膦(PPh3)和4-甲基吡啶(pic),反应生成了配合物[Pd(L)(D)]。从硫卡巴脒与[Pd(PPh3)2CL2]和[Pd(pic)2CL2]的反应中也可以得到这类混合配体配合物。已测定了配合物[Pd(L1)(PPh3)]和[Pd(L2)(pic)]的晶体结构。[Pd(L)(D)]配合物具有特征的1H NMR图谱与明显的可见光区和紫外区吸收。它们在环境温度下可见光区也具有强荧光。这类配合物与四个临床药物即顺铂、BCNU、5-氟尿嘧啶(5-FU)和羟基脲共同进行了体外细胞毒性屏幕测试,测试对象为两个人类癌细胞系,即早幼粒细胞白血病HL-60和组织细胞淋巴瘤U-937。与上述两种细胞系中作为参比试剂的抗癌药物相比,[Pd(L2)(PPh3)]显示了最低的IC50值,其细胞毒性更为明显。用[Pd(L2)(PPh3)]在HL-60细胞上进行的凋亡研究证实,10μM浓度下的该配合物诱导细胞凋亡的程度要大于顺铂和喜树碱。
• 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.