Synthesis, characterizations, and computational studies of new tetrasubstituted imidazole containing a benzothiazole moiety

被引：2

作者：

Al-Jorani, Kamal Rashid ^{[1
]}

Abbood, Ammar Ferman ^{[1
]}

Ali, Atheer Abdulsahib ^{[1
]}

Kadhim, Mustafa M. ^{[2
]}

Hamdan, Salam Dawood ^{[1
]}

机构：

[1] Wasit Univ, Coll Sci, Dept Chem, Wasit 52002, Iraq

[2] Al Farahidi Univ, Med Lab Tech Dept, Baghdad, Iraq

来源：

STRUCTURAL CHEMISTRY | 2023年 / 34卷 / 03期

关键词：

Imidazole; Benzothiazole; Docking; DFT; Breast cancer;

D O I：

10.1007/s11224-022-02069-w

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

Tetrasubstituted imidazoles containing a benzothiazole moiety can be formed by a one-pot three-component synthesis from aldehydes, benzil, and 1,3-benzothiazol-2-amine. The synthesized compounds (1-4) are characterized by Fourier-transform infrared spectroscopy (FT-IR), nuclear magnetic resonance spectroscopy (C-13, H-1 NMR), and mass spectra. The derivatives (1-4) were predicted as anti-breast cancer by docking and DFT study utilization. Discovery Studio Visualizer (DSV) and MGL (Molecular Graphic Laboratory) performed the Autodock procedure. Molecules' adsorption sites were revealed by measuring the total electron density (TED). Furthermore, variables were utilized to determine which of the molecules were more efficient than the others. The binding energy (Eb) of organic compounds was employed in docking simulations to investigate the inhibitory ability. DFT and docking revealed that 1, 2, and 3 were the most effective inhibitory positions.

引用

页码：1143 / 1156

页数：14

共 38 条

[1] Antimicrobial, computational, and molecular docking studies of Zn (II) and Pd (II) complexes derived from piperidine dithiocarbamate [J].

Al-Janabi, Ahmed S. M. ;

Kadhim, Mustafa M. ;

Al-Nassiry, Amenah I. A. ;

Yousef, Tarek A. .

APPLIED ORGANOMETALLIC CHEMISTRY, 2021, 35 (02)

[2]

Al-Saadi ZN, 2018, SYNTHESIS CHARACTERI, V10, P2866

[3] (2E)-2-[1-(1,3-Benzodioxol-5-yl)-3-(1H-imidazol-1-yl)propylidene]-N-(4-methoxyphenyl)hydrazinecarboxamide: Synthesis, crystal structure, vibrational analysis, DFT computations, molecular docking and antifungal activity [J].

Al-Wabli, Reem, I ;

Al-Ghamdi, Alwah R. ;

Primsa, I. P. ;

Ghabbour, Hazem A. ;

Al-Agamy, Mohamed H. ;

Joe, I. Hubert ;

Attia, Mohamed, I .

JOURNAL OF MOLECULAR STRUCTURE, 2018, 1166 :121-130

[4] Gabedit-A Graphical User Interface for Computational Chemistry Softwares [J].

Allouche, Abdul-Rahman .

JOURNAL OF COMPUTATIONAL CHEMISTRY, 2011, 32 (01) :174-182

[5] 2-substituted benzothiazoles as antiproliferative agents: Novel insights on structure-activity relationships [J].

Ammazzalorso, Alessandra ;

Carradori, Simone ;

Amoroso, Rosa ;

Fernandez Fernandez, Inmaculada .

EUROPEAN JOURNAL OF MEDICINAL CHEMISTRY, 2020, 207

[6] Synthesis of 1,2-benzisoxazole tethered 1,2,3-triazoles that exhibit anticancer activity in acute myeloid leukemia cell lines by inhibiting histone deacetylases, and inducing p21 and tubulin acetylation [J].

Ashwini, Nanjundaswamy ;

Garg, Manoj ;

Mohan, Chakrabhavi Dhananjaya ;

Fuchs, Julian E. ;

Rangappa, Shobith ;

Anusha, Sebastian ;

Swaroop, Toreshettahally Ramesh ;

Rakesh, Kodagahalli S. ;

Kanojia, Deepika ;

Madan, Vikas ;

Bender, Andreas ;

Koeffler, H. Phillip ;

Basappa ;

Rangappa, Kanchugarakoppal S. .

BIOORGANIC & MEDICINAL CHEMISTRY, 2015, 23 (18) :6157-6165

[7] Biological activities of the natural imidazole-containing peptidomimetics n-acetylcamosine, carcinine and L-carnosine in ophthalmic and skin care products [J].

Babizhayev, MA .

LIFE SCIENCES, 2006, 78 (20) :2343-2357

[8] The Protein Data Bank [J].

Berman, HM ;

Westbrook, J ;

Feng, Z ;

Gilliland, G ;

Bhat, TN ;

Weissig, H ;

Shindyalov, IN ;

Bourne, PE .

NUCLEIC ACIDS RESEARCH, 2000, 28 (01) :235-242

[9]

Bhagdev K., 2021, Int. Electron. Conf. Mol. Sci, V7, P9, DOI [10.3390/ECMS2021-10839, DOI 10.3390/ECMS2021-10839]

[10] Benzothiazoles: From recent advances in green synthesis to anti-cancer potential [J].

Dhadda, Surbhi ;

Raigar, Ashok Kumar ;

Saini, Kamlesh ;

Guleria, Anjali .

SUSTAINABLE CHEMISTRY AND PHARMACY, 2021, 24

← 1 2 3 4 →