Schiff Base Analogues Research Articles

Green synthesis of Tacrine modified Schiff bases as anti-Alzheimer Agents: An effective strategy validated through in-silico and in-vitro analysis

A variety of Tacrine-modified Schiff base analogues were developed via solvent free (green) method and structurally elucidated using 1HNMR, FTIR and UV–Vis analysis. High product yield was obtained from the synthesised molecules, which were produced efficiently at room temperature without the need of a solvent. The developed molecules were subsequently assessed for their potential to inhibit acetylcholinesterase (AChE) and butyrylcholinesterase (BChE). These molecules revealed effective inhibition of AChE and BChE enzymes with IC50 values varying from 0.1 ± 0.02 to 0.3 ± 0.03 μM and 0.065 ± 0.01 to 0.3 ± 0.03 μM respectively. Compared to the standard Tacrine which has IC50 values of 0.35 ± 0.02 μM for AChE and 0.1 ± 0.01 μM for BChE. Notably, compound 3f showed strong inhibition among others for both the enzymes. The structure–activity relationship of derivatives synthesized were verified and established through molecular docking studies. Theoretical ADME studies also predicted excellent drug-likeness for all the synthesized molecules. Antioxidant activities were also assessed because elevated oxidative stress levels are linked with cognitive loss in Alzheimer's disease (AD). These findings suggest that the lead compound is potentially an effective inhibitor for the therapeutic management of AD.

Insights into the role of potent thiadiazole based Schiff base derivatives in targeting type-II diabetes: A combine in-vitro and in-silico approaches

A novel series of varied substituted thiadiazole based Schiff base analogues (1–21) were designed and characterized using NMR (13C, 1H) and HREI-mass spectrometry, and secerned against the enzymes responsible for hyperglycemia i-e α-amylase and α-glucosidase. Newly designed analogues demonstrated distinct inhibitory activities having IC50= 1.10 ± 0.50 to 21.40 ± 0.20 µM (for alpha-amylase) and 2.50 ± 0.05 to 21.40 ± 0.10 µM (for alpha-glucosidase) in contrast to acarbose a well-known marketed drug (IC50 = 3.16 ± 0.22 & 4.8 ± 0.21 µM for α-amylase and α-glucosidase, respectively). Compound (20) with tri-fluoromethyl at para position of aromatic ring revealed as lead candidate among the members of synthesized series, having effective inhibitory activity against enzymes α-amylase and α-glucosidase. The excellent activity of compound (20) might be due to involvement of fluoro atom interacting via H-bonding with the active sites of enzymes α-amylase and α-glucosidase being targeted. Furthermore, for exploration of binding interactions of potent drugs, molecular docking was performed. For investigation of drug likeness and toxicity, ADME analysis was also conducted.

Synthesis, Characterization, Molecular Docking Studies and Biological Evaluation of Thiazole Schiff Base Analogs

In this work, potentially safe few Schiff base compounds containing a thiazole moiety were synthesized and characterized. Three thiazole derivatives (2a-c) were successfully synthesized through a two-step reaction involving substituted benzaldehyde, thiosemicarbazide and 1,3-dichloroacetone. The elucidation of the synthesized compounds was accomplished by using spectral studies. Antimicrobial activities demonstrated that some compounds exhibited moderate effectiveness against microbes, compared to the standard antibiotic’s ceftriaxone and amphotericin B, using the disc diffusion technique. In the DPPH free radical scavenging assay, all compounds displayed promising antioxidant effectiveness. Moreover, the molecular docking studies showed that thiazole Schiff base analogs effectively bind to potential receptor binding sites.

Synthesis, biological evaluation and molecular docking study of indazole based schiff base analogues as new anti-diabetic inhibitors

Indazole-based Schiff base analogues (1–27) were synthesized by a three-step reaction pathway starting from 1-methyl-1H-indazole-3-carboxylic acid as the basic compound. The structure of the new indazoles was characterized and confirmed by mass spectral analyses as well as NMR spectroscopic data. All synthesized analogues were screened for their in vitro α-glucosidase and α-amylase inhibitory activities. All analogues of the series exhibited good inhibitory potentials, with IC50 values ranging from 0.40 ± 0.01 to 16.20 ± 0.30 µM for α-glucosidase and 0.70 ± 0.01 to 17.40 ± 0.30 µM for α-amylase as compared to the standard drug acarbose (IC50 = 12.90 ± 0.10 and 12.80 ± 0.10 µM, respectively). The most effective analogue of the series is analogue 22 having 3‑hydroxyl groups with an IC50 value of 0.40 ± 0.01 µM and 0.70 ± 0.01 µM for α-glucosidase and α-amylase, respectively. Structure-activity relationship was carried out, which mainly depends upon the nature, number, position, and electron donating/withdrawing effect of the substituent(s) attached to the phenyl ring. To investigate the binding interaction of the potent analogue with the active site of an enzyme, molecular docking studies were carried out.

Ni(II) complexes with in-situ generated N, O-bidentate aroylhydrazone Schiff base ligands: One-pot synthesis, characterization, crystal structure, and in-silico studies

A series of novel aroylhydrazone-based Ni(II) complexes were synthesized by using analogous Schiff base ligands prepared in-situ by reacting 4-[(4-methylbenzyl)oxy]benzoylhydrazine with different aldehydes in the presence of Ni(II) acetate tetrahydrate. The correspondent [NiL2] complexes, 4-7, were characterized by physicochemical techniques, viz., molar conductance, magnetic susceptibility measurement, IR, NMR, and mass spectroscopic techniques. The single-crystal X-ray structural analyses of complexes 4, 6 and 7 showed a distorted square-planar geometry for Ni atoms with deprotonated ligands in trans-configuration bound via azomethine-N and carbonylate-O atoms. Next, quantum chemical methods were incorporated to investigate their thermochemical, molecular orbital, and electrostatic potential properties. Computer-aided drug design methods were also implemented to assess their medicinal, pharmacological, and toxicological properties. Molecular docking and interaction analyses disclosed their potential binding affinity against human lung Cytochrome P450 2A13 receptor protein. Pharmacokinetic and toxicological studies suggest their relatively safe drug administrative properties.

In-Silico Prediction of Novel Fused Quinazoline Based Topoisomerase Inhibitors as Anticancer Agents.

The prospective uses of tryptanthrin and its analogues in cancer chemotherapy are well known, and they are also predicated on their capacity to reverse drug resistance in cancer therapy. The current project entails developing a novel hybrid analogue that includes modifying the tryptanthrin molecule at the C-6 carbonyl position and is expected to exhibit substantial anticancer action. In the ATPase domain of human topoisomerase II, a series of 162 substituted Schiff base analogues of tryptanthrin were developed, and molecular docking experiments were done using Gold 5.1 software interfaced with Hermes 1.6.2. (PDB ID: 1ZXM). Most of the compounds were found to have Goldscore above 100 and formed interactions with the residues like ASN91, ALA92, ASN95, ARG98, ASN120, ILE125, ILE141, PHE142, SER149, THR215, and ILE217. Compound RK-149 had highest Goldscore of 132.59, forming an interaction with ASN91 but had a lesser Goldscore as compared to the standard drug etoposide and had a better score than tryptanthrin. The nitrogen in the imine bond of the proposed compounds is responsible for significant interactions, demonstrating their anticancer potential.

Promising Schiff bases in antiviral drug design and discovery.

Emerging and re-emerging illnesses will probably present a new hazard of infectious diseases and have fostered the urge to research new antiviral agents. Most of the antiviral agents are analogs of nucleosides and only a few are non-nucleoside antiviral agents. There is quite a less percentage of marketed/clinically approved non-nucleoside antiviral medications. Schiff bases are organic compounds that possess a well-demonstrated profile against cancer, viruses, fungus, and bacteria, as well as in the management of diabetes, chemotherapy-resistant cases, and malarial infections. Schiff bases resemble aldehydes or ketones with an imine/azomethine group instead of a carbonyl ring. Schiff bases have a broad application profile not only in therapeutics/medicine but also in industrial applications. Researchers have synthesized and screened various Schiff base analogs for their antiviral potential. Some of the important heterocyclic compounds like istatin, thiosemicarbazide, quinazoline, quinoyl acetohydrazide, etc. have been used to derive novel Schiff base analogs. Keeping in view the outbreak of viral pandemics and epidemics, this manuscript compiles a review of Schiff base analogs concerning their antiviral properties and structural-activity relationship analysis.

Exploring thiazole-based Schiff base analogs as potent α-glucosidase and α-amylase inhibitor: their synthesis and in-silico study

In search of potent antidiabetic agents here in this study a new series of thiazole-based Schiff base analogs (1–20) have been synthesized, characterized by 1HNMR, 13CNMR, HREI-MS and evaluated as dual inhibitor for α-glucosidase and α-amylase. All analogs of the series found active and exhibited variable degree of inhibitory potential ranging from 1.10 ± 0.10–17.20 ± 0.30 µM as compared to reference drug acarbose IC50 = for 9.80 ± 0.20 µM α-glucosidase and from 0.90 ± 0.01 to 16.20 ± 0.30 µM as compared to reference drug acarbose IC50 = 10 0.30 ± 0.20 µM for α-amylase. Compounds 3, 5, 6, 7, 14, 15, 16, 18 and 19 exhibited outstanding α-glucosidase as well as α-amylase inhibitory potential as compared to reference drug acarbose. Structure activity relationships SAR) have established for all the synthesized analogs. A molecular docking study has been conducted to develop an idea about binding interaction of compounds and enzymes. All synthesized compounds were tested for cytotoxicity and found nontoxic.

Synthesis, spectral characterization of pyrazole derived Schiff base analogs: molecular dynamic simulation, antibacterial and DNA binding studies

We have synthesized the pyrazole-bearing Schiff base derivatives (5a–5e) and (6a–6h) then the structural confirmation was supported by various spectral analyses. The antibacterial activity of all analogs was screened against bacterial strains Staphylococcus aureus, Bacillus subtilis, Enterococcus faecalis, Escherichia coli, Klebsiella pneumonieae and Pseudomonas aeruginosa. In comparison to the reference drug ciprofloxacin, the lead analogs 5c and 6c showed potent activity, with MIC values of 64 µg/mL against E. coli and B. subtilis. Compound 5c showed a moderate effect with a MIC value of 128 µg/mL against B. subtilis, P. aeruginosa and K. pneumonieae, while compound 6c was against E. coli and P. aeruginosa. Furthermore, the compounds 5c and 6c displayed groove binding mode towards CT-DNA by absorption, emission, competitive fluorescence studies using EtBr, CD and time-resolved fluorescence studies. Thermodynamic parameters of analogs 5c and 6c with CT-DNA were also calculated at 298, 303 and 308K temperatures by UV–visible spectroscopy. The molecular docking studies give the docking score for all compounds with PDB codes: 1BNA and 2XCT. The MD simulation study of analogs 5c and 6c was also carried out. The pharmacokinetic and ADME properties were calculated for all of the synthesized analogs (5a–5e) and (6a–6h).Communicated by Ramaswamy H. Sarma

Synthesis, Spectroscopic Analysis, Biological Evaluation, and In Silico Studies of Novel Benzenesulfonate-Derived Schiff-Mannich Bases

In the current study, 3-formyl phenyl benzenesulfonate is created by reacting 3-hydroxybenzaldehyde with benzene sulfonyl chloride, which is aided by triethylamine. Nine unique (Z)-3-[(3-substituted-5-oxo-1,5-dihydro-4H-1,2,4-triazol-4-yl)-iminomethyl] compounds were formed through the reaction of a manufactured 3-formyl phenyl benzenesulfonate chemical with nine 3-alkyl(aryl)-4-amino-4,5-dihydro-1H-1,2,4-triazol-5-one, as detailed in the existing literature. Phenyl benzene sulfonate (S) compounds were purchased. Through the reaction of the Schiff bases that were made a secondary amine, such as morpholine with formaldehyde, heterocyclic Mannich bases of a unique kind were created. Five recently found (Z)-3-[(3-substituted-5-oxo-1,5-dihydro-4H-1,2,4-triazol-4-yl)-iminomethyl] compounds are presented in this work. By reacting phenyl benzene sulfonate (S) with morpholine in the presence of formaldehyde, five new (Z)-3-[(3-substituted-1-(morpholinomethyl)-5-oxo-1,5-dihydro-4H-1,2,4-triazol-4-yl)-iminomethyl] compounds were created. Chemical compounds fall under the category of phenylbenzene sulfonates (M). Utilizing IR, 1H NMR, and 13C NMR spectroscopy, fourteen recently novel compoundsand#39; chemical structures were examined. The ability of the freshly synthesized Schiff and morpholine-derived Mannich bases to obstruct the acetylcholinesterase enzymeand#39;s (AChE) activity was also assessed. The 1,2,4-triazole functional group was modified by adding various groups at the 1 and 3 positions, resulting in a collection of compounds (S1–9 and M1, 2, 4, 5, 7). It was determined whether these synthetic compounds could prevent the human recombinant AR enzyme from working in vitro, and the findings were validated using molecular docking, molecular mechanics, and ADME analyses. To better understand this mechanism, synthetic Schiff and Mannich base derivatives as well as the positive control substance quercetin were tested using molecular docking against the human recombinant AR enzyme in vitro. To assess the drug-like properties of Schiff and Mannich base analogs, a series of absorption, distribution, metabolism, and excretion (ADME) properties were analyzed theoretically.

Equilibria of complexes in the aqueous cobalt(II)–N-(2-hydroxybenzyl)phenylalanine system and their biological activity compared to analogous Schiff base structures

Due to their excellent prospects in biological applications, Schiff bases and their complexes are a source of continuing interest. The present study examines the formation of four cobalt(II) complexes with the reduced Schiff base N-(2-hydroxybenzyl)phenylalanine (PhAlaSal) in alkaline aqueous solution by pH-metry. UV–Vis and ESI–MS studies confirmed the model of proposed species. Kinetic analysis indicated that the single- and bi-ligand cobalt(II) complexes transitioned from octahedral to tetrahedral structures. The Schiff base and its complexes detected under physiological pH were tested for antimicrobial abilities and compared with analogous structures of the Schiff base derivative, N-(2-hydroxybenzyl)alanine (AlaSal). The ability of these structures to influence cell growth was tested on L929 mouse fibroblasts and on cervix and gastric adenocarcinoma cancer cell lines. N-(2-hydroxybenzyl)phenylalanine demonstrates greater antimicrobial efficacy than N-(2-hydroxybenzyl)alanine but also higher cytotoxicity; however, it is nonetheless effective against cancer cells. In turn, AlaSal demonstrates low cytotoxicity for fibroblasts and high cytotoxicity for gastric adenocarcinoma epithelial cells at bacteriostatic concentration for Helicobacter pylori and Candida strains. The presence of these microorganisms in the gastric milieu supports the development of gastritis and gastric cancer; AlaSal therapy may be simultaneously effective against both. Due to their cytotoxicity, Schiff base complexes are not suitable for use against fungal and bacterial infections, but may effectively prevent cancer cell growth. Data availabilityData will be made available on request.

1,2,4-Triazole-3-Thione Analogues with a 2-Ethylbenzoic Acid at Position 4 as VIM-type Metallo-β-Lactamase Inhibitors.

Metallo-β-lactamases (MBLs) are increasingly involved as a major mechanism of resistance to carbapenems in relevant opportunistic Gram-negative pathogens. Unfortunately, clinically efficient MBL inhibitors still represent an unmet medical need. We previously reported several series of compounds based on the 1,2,4-triazole-3-thione scaffold. In particular, Schiff bases formed between diversely 5-substituted-4-amino compounds and 2-carboxybenzaldehyde were broad-spectrum inhibitors of VIM-type, NDM-1 and IMP-1 MBLs. Unfortunately, these compounds were unable to restore antibiotic susceptibility of MBL-producing bacteria, probably because of poor penetration and/or susceptibility to hydrolysis. To improve their microbiological activity, we synthesized and characterized compounds where the hydrazone-like bond of the Schiff base analogues was replaced by a stable ethyl link. This small change resulted in a narrower inhibition spectrum, as all compounds were poorly or not inhibiting NDM-1 and IMP-1, but showed a significantly better activity on VIM-type enzymes, with Ki values in the μM to sub-μM range. The resolution of the crystallographic structure of VIM-2 in complex with one of the best inhibitors yielded valuable information about their binding mode. Interestingly, several compounds were shown to restore the β-lactam susceptibility of VIM-type-producing E. coli laboratory strains and also of K. pneumoniae clinical isolates. In addition, selected compounds were found to be devoid of toxicity toward human cancer cells at high concentration, thus showing promising safety.

The involvement of triplet states in the isomerization of retinaloids.

Rhodopsins form a family of photoreceptor proteins which utilize the retinal chromophore for light energy conversion. Upon light absorption the retinal chromophore undergoes a photoisomerization. This reaction involves a non-radiative relaxation through a conical intersection between the singlet excited state and the ground state. In this work we studied the possible involvement of triplet states in the photoisomerization of retinaloids using the extended multistate (XMS) version of CASPT2. To this end, truncated models of three retinaloids were considered: protonated Schiff base, deprotonated Schiff base and the aldehyde form. The optimized geometries of the reactant, the product and the conical intersection were connected by a linear interpolation of internal coordinates to describe the isomerization. The energetic position of the low-lying singlet and triplet states as well as their spin-orbit coupling matrix elements (SOCME) were calculated along the isomerization profile. The SOCME values peaked in vicinity of the conical intersection for all the retinaloids. Furthermore, the magnitude of SOCME is invariant to the number of double bonds in the model. The SOCME for the protonated Schiff base is negligible (1.5 cm-1) which renders the involvement of the triplet state as improbable. However, the largest SOCME value of 30 cm-1 was found for the aldehyde form, followed by 15 cm-1 for the deprotonated Schiff base.

Nickel(II) Complex of N4 Schiff Base Ligand as a Building Block for a Conducting Metallopolymer with Multiple Redox States

Metal–ligand interactions in monomeric and polymeric transition metal complexes of Schiff base ligands largely define their functional properties and perspective applications. In this study, redox behavior of a nickel(II) N4-anilinosalen complex, [NiAmben] (where H2Amben = N,N′-bis(o-aminobenzylidene)ethylenediamine) was studied by cyclic voltammetry in solvents of different Lewis basicity. A poly-[NiAmben] film electrochemically synthesized from a 1,2-dichloroethane-based electrolyte was investigated by a combination of cyclic voltammetry, electrochemical quartz crystal microbalance, in situ UV-Vis spectroelectrochemistry, and in situ conductance measurements between −0.9 and 1.3 V vs. Ag/Ag+. The polymer displayed multistep redox processes involving reversible transfer of the total of ca. 1.6 electrons per repeat unit, electrical conductivity over a wide potential range, and multiple color changes in correlation with electrochemical processes. Performance advantages of poly-[NiAmben] over its nickel(II) N2O2 Schiff base analogue were identified and related to the increased number of accessible redox states in the polymer due to the higher extent of electronic communication between metal ions and ligand segments in the nickel(II) N4-anilinosalen system. The obtained results suggest that electrosynthesized poly-[NiAmben] films may be viable candidates for energy storage and saving applications.

Synthesis, identification of some new derivatives of 4-amino antipyrine bearing six and seven membered rings

In this paper, we consider the Synthesis of a series of various 4-amino antipyrine derivatives containing 1,3-thiazinan-4-one, 1,3-oxazinan-6-one, and 1,3-oxazepin-4,7-dione in its structure. These derivatives were obtained via cycloaddition of the methenamine group in Schiff base analog of 4-amino antipyrine with 3-mercaptopropanoic acid, 3-chloropropanoic acid, maleic and citraconic anhydride, respectively. The Schiff bases were prepared in excellent yields by condensation of 4-amino antipyrine with 3-nitro- or 3-bromobenzaldehyde in n-butanol. We characterize the desired products by C.H.N.S analysis, FT-IR, and 1HNMR spectroscopy.

Synthesis, Anti-inflammatory Activity, and In Silico Studies of Some New 3-({P-Dimethylamino}benzylidenehydrazinylidene)-1,3-dihydro-2H-indole-2-one Derivatives.

Ten novel isatin Schiff base analogs have been designed using a combination of isatin, hydrazine hydrate, and para-dimethylaminobenzaldehyde. Molecular docking studies have been performed to study the binding interactions of the designed compounds with COX-2 protein as a target (PDB code: 3LN1). The ten novel 3-({p-dimethylamino}benzylidenehydrazinylidene)-1,3-dihydro-2H-indole-2-one derivatives (IIIa-IIIj) were synthesized. Structures of all compounds were elucidated by using IR, 1H NMR, and mass spectra. The compounds which have docked to the COX-2 protein with good score have been investigated for their anti-inflammatory activity using carrageenan-induced rat paw edema method. Compounds IIIe, IIIf, IIIg, IIIh, and IIIi showed anti-inflammatory activity at 100mg/kg compared with the standard drug indomethacin at 10mg/kg. Out of these compounds, IIIe, IIIf, and IIIg showed a good anti-inflammatory activity. Thus, the synthesized compounds could be considered as a new anti-inflammatory hit for further lead optimization.

Efficient and Facile Synthesis of Benzimidazole Induced Schiff Bases and their Potent Antibacterial Activity and Computational Study

Synthesized benzimidazole induced Schiff base analogues were characterized by mass, 13C NMR, 1H NMR and UV-visible spectroscopy. To get more information about binding mechanism, molecular docking studies were carried out and the obtained results concluded that the compounds could effectively bind with receptor. in vitro Antibacterial screening was carried out against four strains (S. aureus, B. subtilis, P. aeruginosa and E. coli) and exhibited good antibacterial activity. The gastrointestinal absorption (HIA) and brain penetration (BBB) was evaluated by The BOILED-Egg model, which showed that two compounds anticipated being effectively effluated by the P-glycoprotein from central nervous system after penetration and can accounts for brain access and passive gastrointestinal absorption. Computational screening showed 0.55 bioavailability score for all synthesized compounds.

Chemistry of Tetradentate [C,N : C,N] Iminophosphorane Palladacycles: Preparation, Reactivity and Theoretical Calculations.

A theoretical and experimental study of tetradentate [C,N : C,N] iminophosphorane palladacycles was carried out for the purpose of elucidating their behavior as compared to the parent Schiff base analogues to determine the prospect of encountering new A‐frame structures for the iminophosphorane derivatives. The DFT calculations were in agreement with the experimental results regarding the performance of these ligands. New insights into the chemistry of the related dinuclear species have been obtained.

Synthesis, in vitro alpha glucosidase, urease activities and molecular docking study of bis-indole bearing Schiff base analogs

Abstract We have synthesized fifteen bis-indole bearing Schiff base derivatives (1-15) as α-glucosidase and urease inhibitors which were characterized through different spectroscopic techniques (1H, 13C-NMR, HREI-MS and FTIR). All analogs were found active when screened for α-glucosidase inhibition and showed IC50 values ranging from 18.92 ± 1.34 to 475.74 ± 1.52 µM when compared with standard acarbose (IC50 = 375.82 ± 1.76 µM). Among the series, analogs 10, 14 and 15 having IC50 values 18.92 ± 1.34, 39.25 ± 1.28 and 92.46 ± 1.43 µM respectively showed outstanding inhibitory potential. Against urease enzyme; most of analogs were found active and show IC50 values ranging from 19.59 ± 1.53 to 236.24 ± 1.49 µM when compared with standard thiourea (IC50 = 21.37 ± 1.26 µM). Among the series, analog 10 having IC50 value 19.59 ± 1.53 µM showed an excellent inhibitory potential. Structure activity relationship was established. Molecular docking study was carried out to confirm binding interactions.

Chair- and V-Shaped of H-bonded Supramolecular Complexes of Azophenyl Nicotinate Derivatives; Mesomorphic and DFT Molecular Geometry Aspects.

New geometrical architectures of chair- and V-shaped supramolecular liquid crystalline complexes were molded through 1:1 intermolecular hydrogen bonding interactions between 4-(4-(hexyloxy)phenylazo)methyl)phenyl nicotinate and 4-alkoxybenzoic acids. The length of terminal alkoxy acid chains varied, n = 6 to 16 carbons. The mesomorphic behaviour of these complexes was examined through differential scanning calorimetry (DSC) and polarizing optical microscopy (POM). Fourier-transform infrared spectroscopy (FT-IR) was carried out to confirm the presence of Fermi bands that appeared for the hydrogen bonding formation. Enantiotropic nematic phases were observed and covered all lengths of alkoxy chains. The geometrical structures of the prepared supramolecular complexes geometries were estimated by Density functional theory (DFT) calculations. The supramolecular complexes I/An are projected to exhibit a nonlinear geometry with V-shaped and chair-shaped geometry. The chair-shaped conformers of I/An were found to be more stable than V-shaped isomeric complexes. Moreover, the effect of the change of the mesogenic core on the mesophase thermal stability (TC) has been investigated by a comparative study of the present azo supramolecular H-bonding LCs (SMHBCs) I/An and our previously reported their Schiff base analogue complexes, II/An. The findings of the DFT illustrated the high impact of CH=N as a mesogenic core on the mesomorphic behavior in terms of the competitive lateral and terminal intermolecular interactions as well as the molecular electrostatic potential (MEP).