1-((dodecylimino)methyl)naphthalen-2-ol | 17255-51-5

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: 1-((dodecylimino)methyl)naphthalen-2-ol
• 英文别名: 2-Hydroxy-α-naphthylmethylidene-laurylamine；<2-Hydroxy-<1>naphthylmethylen>-dodecyl-amin；N-dodecyl-5,6-benzosalicylideneamine；1-(Dodecyliminomethyl)naphthalen-2-ol
• CAS: 17255-51-5
• 化学式: C₂₃H₃₃NO
• 分子量: 339.521
• InChiKey: MRLORLHWWRZTOQ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  8
• 重原子数：
  25
• 可旋转键数：
  12
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.52
• 拓扑面积：
  32.6
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  1-((dodecylimino)methyl)naphthalen-2-ol 在 LiCl 、 hydrochloric acid 作用下， 以 乙醇 、 异丙醇 为溶剂， 生成 dichlorobis(N-dodecyl-5,6-benzosalicylideneaminato)manganese(IV)
  参考文献：
  名称：

  Preparation and characterization of dichlorobis(N-alkyl-substituted salicylideneaminato)manganese(IV) complexes

  摘要：

  DOI：

  10.1016/s0277-5387(00)81520-x
• 作为产物：
  描述：

  十二烷基伯胺 、 2-羟基-1-萘甲醛 以 乙醇 为溶剂， 反应 1.0h， 以85.2%的产率得到1-((dodecylimino)methyl)naphthalen-2-ol
  参考文献：
  名称：

  Pudovik 反应：合成具有长烷基链的生物活性 α-氨基膦酸酯

  摘要：

  摘要 在这项研究中，我们研究了取代萘醛与胺的反应。do-、tetra-、hexa-、octadecan-1-胺与2-羟基-1-萘醛的缩合以良好的产率产生了一系列偶氮甲碱。这些化合物与双十二烷基氧化膦的后续反应产生了 α-氨基膦酸酯。合成的磷化合物对革兰氏阳性菌、革兰氏阴性菌和酵母白色念珠菌的体外微生物活性与标准试剂进行比较。合成的化合物对人和动物病原微生物菌群表现出很高的抗菌和抗真菌活性。每个新合成的化合物都通过元素分析、IR、1H NMR、31P NMR 光谱研究进行表征。通过同步热重法和差示扫描量热法(TG/DSC)研究热稳定性。图形概要

  DOI：

  10.1080/10426507.2018.1539848

文献信息

• Structures and properties of di-μ-oxo dimanganese(IV) complexes with bidentate Schiff bases, N-alkyl-substituted-salicylideneamine
  作者：Hitoshi Torayama、Hideyuki Asada、Manabu Fujiwara、Takayuki Matsushita

  DOI：10.1016/s0277-5387(98)00144-2

  日期：1998.11

  Novel di-mu-oxo dimanganese(IV) complexes, [Mn-IV(N-R-X-sal)(2)(mu-O)](2), with bidentate Schiff base ligands, N-alkyl-substituted-salicylideneamine, N-R-X-salH [R= CH3(Me), C2H5 (Et), n-C3H, (Pr), n-C4H9 (Bu), n-C6H13 (Hx), n-C8H17 (Oct), II-C10H21 (Dec), n-C12H25 (Dod), or n-C18H37 (Octd) and X = H or 5,6-benzo]: have been prepared by their reaction with potassium permanganate (KMnO4) in MeCN, while stirring at room temperature. These complexes were characterized by spectroscopy, magnetic susceptibility, thermal analysis and X-ray crystallography. The structures consist of a Mn-2(IV)(mu-O)(2) core with a Mn-Mn separation of 2.731 (4) Angstrom for [Mn-IV(N-Me-sal)(2)(mu-O)](2), 1, 2.769(2) Angstrom for [Mn-2(IV)(N-Et-sal)(2)(mu-O)](2), 2, 2.780(2) Angstrom for [(Mn-IV-Hx-sal)(2)(mu-O)](2), 5, 2.780(2)Angstrom for [Mn-IV(N-Dec-sal)(2)(mu-O)](2), 7, and 2.756(3) Angstrom for [Mn-IV(N-Me-5,6-benzo-sal)(2)(mu-O)](2), 10. The complex 1 is the first di-mu-oxo dimanganese(IV) complex having asymmetrical form in which two manganese ions adopt different configurations each other. Moreover, the complexes 5 and 7 are found to exhibit the longest one among all of the Mn-Mn separation observed for the structurally characterized Mn-2(mu-O)(2) complexes prior to this work. The antiferromagnetic exchange interaction has been found to be J= -83 and -188 cm(-1) for 1 and 7, respectively. (C) 1998 Elsevier Science Ltd. All rights reserved.
• Interplay between Supramolecular and Coordination Interactions in Synthetic Amphiphiles: Triggering Metal Starvation and Anchorage onto MRSA Cell Surface
  作者：Poulomi Dey、Gopal Das、Aiyagari Ramesh

  DOI：10.1021/acs.langmuir.9b03073

  日期：2020.3.3

  The present work highlights the implications of supra-molecular interaction and metal coordination on the self-assembly behavior and bactericidal potential of salicaldehyde-(C1) and napthaldehyde-based (C2) amphiphiles against methicillin-resistant Staphylococcus aureus (MRSA). LB trough and atomic force microscope (AFM) analysis indicated the propensity of the amphiphiles to form a monolayer as well as spherical aggregates, with the critical micelle concentration (CMC) for C2 (7.0 mu M) being lower than C1 (18.5 mu M) in water. Formation of an amphiphile-metal complex was evidenced by ESI-MS, FTIR, FETEM-EDX, and ITC analysis. Growth of S. aureus MRSA 100 cells was remarkably impaired in the presence of 5.0 mu M C1 or 20 mu M C2 as compared to free cells or cells grown in the presence of equivalent levels of amphiphile-metal complexes, suggesting that the amphiphiles perhaps sequester metal and induce metal starvation in MRSA. C1 and C2 rendered superior membrane damage in MRSA and were less toxic to human embryonic kidney (HEK 293) cells as compared to their metal complexes. C1 and C2 rendered a dose-dependent inhibition of S. aureus biofilm formation, while revival of biofilm upon Zn(II) addition suggested that zinc starvation rendered by the amphiphiles may induce biofilm inhibition. C1 imposed a concentration-dependent metal starvation response in MRSA as there was an upregulation of the cntL gene and downregulation of cntA gene, which are involved in synthesis of the zincophore staphylopine (Stp) and transport of the Stp-Zn complex, respectively. ITC analysis revealed that binding of C1 and C2 to staphylococcal lipoteichoic acid (LTA) was stronger than the corresponding Zn(II) complexes, which perhaps accounted for the higher bactericidal potency of the amphiphiles. The study provides a fundamental understanding on how the chemistry-driven multimodal interaction of the amphiphile translates into growth inhibition and metal starvation in MRSA and advances the idea of combating drug resistance in pathogenic bacteria through amphiphiles, which are pluri-active.