Match!

Newly designed organotin(IV) carboxylates with peptide linkage: Synthesis, structural elucidation, physicochemical characterizations and pharmacological investigations

Published on Jan 1, 2018in European Journal of Medicinal Chemistry4.833
· DOI :10.1016/j.ejmech.2017.11.001
Muhammad Sirajuddin17
Estimated H-index: 17
(University of Science and Technology),
Vickie McKee39
Estimated H-index: 39
(DCU: Dublin City University)
+ 1 AuthorsSaqib Ali30
Estimated H-index: 30
(QAU: Quaid-i-Azam University)
Abstract
Abstract Fourteen new organotin(IV) carboxylate complexes with peptide linkage of (2-(4-methoxy-2-nitrophenylcarbamoyl)benzoic acid) were successfully synthesized and characterized by elemental analyses, FT-IR, NMR ( 1 H, 13 C and 119 Sn) and single crystal X-ray techniques. FT-IR results of the sodium salt of 2-(4-methoxy-2-nitrophenylcarbamoyl)benzoic acid and complexes showed that the coordination took place via oxygen atoms of the carboxylate group. 1 J ( 119 Sn- 13 C), 2 J ( 119 Sn- 1 H) and θ values calculated from 1 H and 13 C NMR data using Lockhart's equation reveal a trigonal bipyramidal geometry for triorganotin(IV) derivatives and an octahedral geometry for diorganotin(IV) derivatives. Crystallographic data for three triorganotin(IV) complexes ( 1 – 3 ) showed the tin has distorted trigonal bipyramidal geometry. In vitro anticancer activity against lung carcinoma (H-157) and kidney fibroblast (BHK-21) cell lines as well as antileishmanial activity against the promastigote forms of leishmania major of the synthesized compounds were also studied and the complexes were found biologically active. The in vitro antibacterial activity of most of the synthesized organotin(IV) derivatives against the studied bacterial pathogens is higher than those of the standard 3rd generation antibiotics such as Tetracycline, Penicillin G, Ampicillin, Amoxicillin. This suggest the use of these newly designed organotin(IV) derivatives as potent antibiotics. The synthesized compounds interact with DNA via intercalative mode of interaction. Viscosity measurement results also support the intercalative mode of interaction for the compounds with DNA.
  • References (53)
  • Citations (17)
📖 Papers frequently viewed together
34 Citations
64 Citations
1 Citations
78% of Scinapse members use related papers. After signing in, all features are FREE.
References53
Newest
#1Xiao XiaoH-Index: 8
#2Jingwen Liang (Northeast Normal University)H-Index: 5
Last. Yuan DongH-Index: 2
view all 6 authors...
Abstract Organotin carboxylates based on an amide carboxylic acid 2-(1,3-dioxo-1H-benzo[de]isoquinolin-2(3H)-yl)acetic acid (HL): [(Bn2Sn)2O2L]2·2C6H6 (1) (Bn = benzyl group) and (Ph2Sn)(L)2 (2) were synthesized and characterized by elemental analysis, IR, 1H, 13C, 119Sn NMR spectroscopy and X-ray crystallography diffraction analysis. Complex 1 is dimeric carboxylate tetraorganodistannoxane and show a “ladder-like” molecular structure. Complex 2 is a dialkyltin carboxylate monomer possessing cry...
8 CitationsSource
#1Mala Nath (IITR: Indian Institute of Technology Roorkee)H-Index: 23
#2Mridula (IITR: Indian Institute of Technology Roorkee)H-Index: 3
Last. Ranjana Kumari (IITR: Indian Institute of Technology Roorkee)H-Index: 2
view all 3 authors...
Abstract Diorganotin(IV) and triphenyltin(IV) derivatives of L-proline (HPro) having general formula R 2 Sn(Pro) 2 (R = n -Bu ( 1 ), Ph ( 2 )) and Ph 3 Sn(Pro) ( 3 ), respectively, and the mixed ligands di-/triorganotin(IV) derivatives of L-proline and 1,10-phenanthroline (phen) with general formula [R 2 Sn(Pro)(Phen)Cl] and [R 3 Sn(Pro)(Phen)] (where R = Me ( 4 and 7 ), n -Bu ( 5 and 8 ), Ph ( 6 and 9 )), respectively, have been synthesized by microwave-assisted method and characterized by elem...
6 CitationsSource
#1Kai Liu (Liaocheng University)H-Index: 2
#2Hun Yan (Liaocheng University)H-Index: 1
Last. Min Hong (Liaocheng University)H-Index: 17
view all 6 authors...
Abstract Four new organotin(IV) complexes Me 2 SnL 1 , Ph 2 SnL 1 , Me 2 SnL 2 and Ph 2 SnL 2 (H 2 L 1 = 5-chlorosalicylaldehyde isonicotinoyl hydrazone and H 2 L 2 = 2-hydroxy-4-methoxybenzaldehyde isonicotinoyl hydrazone) have been synthesized and characterized by elemental analyses, FT-IR, NMR ( 1 H, 13 C and 119 Sn) and single crystal X-ray diffraction techniques. The crystal structure analysis shows that complexes 1 and 2 are trinuclear compounds, of which the enolic hydrazone Schiff base l...
24 CitationsSource
#1Ceyda Acilan (TÜBİTAK Marmara Research Center)H-Index: 11
#2Buse Cevatemre (Uludağ University)H-Index: 11
Last. João Costa Pessoa (IST: Instituto Superior Técnico)H-Index: 40
view all 8 authors...
Abstract Background To overcome the hurdles of cisplatin, majorly its toxicity and resistance, there has been extensive search for alternative anti-cancer metal-based compounds. Here, three Cu(II)-complexes, Cu(Sal-Gly)(phen), Cu(Sal-Gly)(pheamine), Cu(Sal-Gly)(phepoxy) are characterized for their interaction with DNA, cytotoxicity and mechanism of action. Methods The binding ability of the complexes to Calf-Thymus DNA was evaluated by competition fluorescence studies with thiazole-orange, UV–Vi...
33 CitationsSource
#1Min Hong (Liaocheng University)H-Index: 17
#2Guoliang Chang (Liaocheng University)H-Index: 6
Last. Meiju Niu (Liaocheng University)H-Index: 14
view all 4 authors...
Five new mono- or di-organotin(IV) complexes, Me2SnL (1), Ph2SnL (2), n-Bu2SnL (3), n-Oct2SnL (4) and n-BuSnCl(H2O)L·CH3CH2OH (5), where H2L is 2-hydroxy-N′-[(2-hydroxy-3-methoxyphenyl)methylidene]-benzohydrazone, were synthesized and characterized by elemental analysis and spectroscopic techniques (IR and 1H, 13C, 119Sn NMR). The crystal structures of all compounds were established by X-ray diffraction, showing the hydrazone Schiff base ligand bound to the tin atom as ONO tridentate chelate. In...
33 CitationsSource
#1Fatima Javed (QAU: Quaid-i-Azam University)H-Index: 7
#2Muhammad Sirajuddin (University of Science and Technology)H-Index: 17
Last. Muhammad Rashid Khan (QAU: Quaid-i-Azam University)H-Index: 34
view all 8 authors...
Abstract A series of organotin(IV) complexes have been synthesized by reacting potassium o-isobutyl carbonodithioate with di- and triorganotin halides in methanol under stirring conditions. The newly synthesized complexes have been characterized by elemental analysis, FT-IR, NMR (1H and 13C) and X-ray crystallography. The FT-IR results show that the ligand acts as bidentate in complexes 1–3 and monodentate in complexes 4 and 5, which were also confirmed by theoretical calculations. The NMR data ...
19 CitationsSource
#1Laijin Tian (Qufu Normal University)H-Index: 11
#2Haixia Yu (Qufu Normal University)H-Index: 1
Last. Xijie LiuH-Index: 2
view all 4 authors...
Two new bis(tricyclohexyltin)benzenedioxyacetates, 1,x-C6H4[OCH2CO2Sn(c-C6H11)3]2 (1: x = 3; 2: x = 4), have been synthesized and characterized by means of elemental analysis, infrared and NMR (1H, 13C and 119Sn) spectra and single-crystal X-ray diffraction. Compound 1⋅H2O⋅CH3OH is a binuclear tin complex containing a four-coordinated tin and a five-coordinated tin and linked by an R33(16) hydrogen bond into a one-dimensional supramolecular chain. Compound 2 is a two-dimensional coordination pol...
8 CitationsSource
#1George M. Sheldrick (GAU: University of Göttingen)H-Index: 52
The new computer program SHELXT employs a novel dual-space algorithm to solve the phase problem for single-crystal reflection data expanded to the space group P1. Missing data are taken into account and the resolution extended if necessary. All space groups in the specified Laue group are tested to find which are consistent with the P1 phases. After applying the resulting origin shifts and space-group symmetry, the solutions are subject to further dual-space recycling followed by a peak search a...
4,446 CitationsSource
The improvements in the crystal structure refinement program SHELXL have been closely coupled with the development and increasing importance of the CIF (Crystallographic Information Framework) format for validating and archiving crystal structures. An important simplification is that now only one file in CIF format (for convenience, referred to simply as `a CIF') containing embedded reflection data and SHELXL instructions is needed for a complete structure archive; the program SHREDCIF can be us...
9,376 CitationsSource
#1Muhammad Sirajuddin (QAU: Quaid-i-Azam University)H-Index: 17
#2Saqib Ali (QAU: Quaid-i-Azam University)H-Index: 30
Last. Hammad Pasha (QAU: Quaid-i-Azam University)H-Index: 1
view all 5 authors...
Abstract Fourteen new organotin(IV) complexes with general formula R 2 SnL 2 or R 3 SnL where R = CH 3 , C 2 H 5 , C 4 H 9 , C 6 H 5 , C 6 H 11 , CH 2 –C 6 H 5 , C(CH 3 ) 3 , C 8 H 17 and L = N-[(2-methoxyphenyl)]-4-oxo-4-[oxy]butanamide were synthesized and characterized by elemental analyses, FT-IR, NMR ( 1 H, 13 C and 119 Sn), mass spectrometry and single crystal X-ray structural analysis. Crystallographic data for four triorganotin(IV) complexes (R 3 SnL, R = CH 3 , C 2 H 5 , C 4 H 9 , CH 2 ...
64 CitationsSource
Cited By17
Newest
#1Muhammad Sirajuddin (University of Science and Technology)H-Index: 17
#2Saqib Ali (QAU: Quaid-i-Azam University)H-Index: 30
Last. Shaukat Ali (Government College University)H-Index: 4
view all 6 authors...
Abstract The carboxylic acid functional group plays a fundamental role in the biochemistry of living systems as well as in drug design by enhancing the hydrophilicity of drugs as well as their polarity which in turn affect their bioavailability. Two new carboxylic acid derivatives with molecular formula C15H12N2O6, (1) and C11H12N2O6 (2) were successfully confirmed by different instrumental techniques. Confirmation by FT-IR and 1H NMR techniques was proved by the presence of the OH peak (3289 cm...
Source
#1Muhammad Sirajuddin (University of Science and Technology)H-Index: 17
#2Saqib Ali (QAU: Quaid-i-Azam University)H-Index: 30
Last. Abdul Matin (Majmaah University)H-Index: 2
view all 4 authors...
Abstract This article focus on the synthesis of three 5-coordinated Sn(IV) complexes based on carboxylate ligand: 4-((4-methoxy-2-nitrophenyl)amino)-4-oxobutanoic acid. The complexes were characterized in both solid state (FT-IR, single crystal XRD and micro elemental analysis) as well as in solution state (1H, 13C and 119Sn NMR) and their results demonstrate that the carboxylate moiety of the ligand is linked with Sn atom. A 5-coordinated trigonal bipyramidal structure was obtained from crystal...
1 CitationsSource
#1Muhammad Zubair (QAU: Quaid-i-Azam University)H-Index: 8
#2Muhammad Sirajuddin (University of Science and Technology)H-Index: 17
Last. Muhammad Nawaz Tahir (UOS: University of Sargodha)H-Index: 38
view all 8 authors...
Abstract Two azomethines: (E)-2-(((2-hydroxyethyl)imino)methyl)-6-methoxyphenol (1) and (E)-3-(((2-hydroxyethyl)imino)methyl)benzene-1,2-diol (2) were synthesized and characterized in solid state by FT-IR spectroscopy and single crystal X-ray crystallography, whereas in solution state by NMR (1H, 13C) and GC-MS. The titled compounds exist in a zwitter ionic form with a strong intramolecular N–H⋯O hydrogen bond between the NH+ and the phenolate O− as observed both in solution states as well as in...
Source
#1Saba Naz (QAU: Quaid-i-Azam University)H-Index: 1
#2Muhammad Sirajuddin (University of Science and Technology)H-Index: 17
Last. Saqib Ali (QAU: Quaid-i-Azam University)H-Index: 30
view all 10 authors...
Abstract 2-Phenylbutyric acid based four organotin (IV) complexes were prepared with general formula R3SnL/R2SnL2, where R = methyl (1), butyl (2), octyl (3) and L = 2-phenylbutyrate. The 2-phenyl butyrate coordinates to the tin atom via carboxylate group as evidenced by FT-IR and 13C NMR data. Moreover, skew-trapezoidal bipyramidal geometry was observed for complex 3 by single crystal X-ray diffraction data. The prepared complexes were evaluated for antibacterial action against four plant patho...
2 CitationsSource
#1Mehr-un-Nisa (QAU: Quaid-i-Azam University)H-Index: 1
#2Muhammad Sirajuddin (University of Science and Technology)H-Index: 17
Last. Muhammad Iqbal (Bacha Khan University)H-Index: 5
view all 5 authors...
Abstract Three zinc metal complexes viz, [Zn(L1)2phen] (1), [Zn2(L2)4(bipy)2] (2) and [Zn(L2)2bipy.H2O] (3) where HL1 = 4-(o-toluidino)-4-oxobutanoic acid and HL2 = 4-(4-nitrophenyl amino)-4-oxobut-2-enoic acid, bipy = 2,2- bipyridine and phen = 1,10-phenenthroline. To elucidate their structure and geometry, the synthesized complexes were characterized by different analytical techniques such as FT-IR, 1H NMR, 13C NMR and single crystal X-ray diffraction analysis. Single crystal X-ray analysis co...
2 CitationsSource
#1Mehtab Parveen (AMU: Aligarh Muslim University)H-Index: 12
#2Afroz Aslam (AMU: Aligarh Muslim University)H-Index: 1
Last. P. S. Pereira Silva (UC: University of Coimbra)H-Index: 11
view all 6 authors...
Abstract An efficient procedure for the one-pot synthesis of 4-arylmethylene-3- methylisoxazol-5-ones from ethyl acetoacetate, hydroxylamine hydrochloride, and various aromatic aldehydes using sodium acetate as a safe, clean, and green catalyst in ethanol is reported. This simple, synthetic and eco-friendly approach resulted in a remarkable improvement in the synthetic efficiency (90–95% yield), high purity, minimizing the production of chemical wastes without using highly toxic reagents for the...
1 CitationsSource
#1Muhammad Zubair (QAU: Quaid-i-Azam University)H-Index: 8
#2Muhammad Sirajuddin (University of Science and Technology)H-Index: 17
Last. Saqib Ali (QAU: Quaid-i-Azam University)H-Index: 30
view all 6 authors...
Source
#1Sachin B. Pandya (SPU: Sardar Patel University)H-Index: 1
#2Urmila H. Patel (SPU: Sardar Patel University)H-Index: 7
Last. Bhupesh S. Bhatt (SPU: Sardar Patel University)H-Index: 12
view all 6 authors...
1 CitationsSource
#1Xiu-Mei Du (Liaocheng University)H-Index: 1
#2Shuo Wang (Liaocheng University)H-Index: 1
Last. Chunlin Ma (Liaocheng University)H-Index: 23
view all 6 authors...
Source
#1Maryam Yousefi (Shahid Chamran University of Ahvaz)H-Index: 2
#2Tahereh Sedaghat (Shahid Chamran University of Ahvaz)H-Index: 14
Last. Mohammad Shafiei (Shahid Chamran University of Ahvaz)H-Index: 3
view all 4 authors...
1 CitationsSource