Synthesis, Crystal Structure, Density Function Theory, Molecular Docking and Antimicrobial Studies of 2-(3-(4- phenylpiperazin-1-yl) propyl) isoindoline-1,3-dione

Purpose: To determine the exact structure and antimicrobial activity of 2-(3-(4 phenylpiperazin-1-yl) propyl) isoindoline-1,3-dione.Methods: 2-(3- (4-Phenylpiperazin-1-yl) propyl) isoindoline-1,3-dione (C21H23N3O2) was synthesized by the reaction of phthalimide with 1,3 dibromopropane to form 2-(3-bromopropyl) isoindoline-1,3-dione, and was then treated with 1-phenylpiperazine in acetonitrile. The structure of the title compound, 2-(3- (4-phenylpiperazin-1-yl)propyl)isoindoline-1,3-dione, was characterized by proton nuclear magnetic resonance spectroscopy (NMR) and single crystal x-ray diffraction method. The target compound was tested for its antimicrobial activities and computational studies including density function test (DFT) and docking studies were performed.Results: The crystal structure is monoclinic, P21/n, a = 10.0047 (3) Å, b = 6.0157 (2) Å, c = 30.8571 (12) Å, β = 90.105 (1) °, V = 1857.14 (11) Å3, Z = 4, wRref(F2) = 0.158, T = 296 K. The molecules are packed in the crystal structure by non-classical intermolecular C–H….O interactions. Besides HOMO– LUMO energy gap was performed at B3LYP/6-31G (d,p) level of theory. The compound exhibited good activity against S. aureus and C. albicans with zones of inhibition of 15 cm and 18 cm, respectivelyConclusion: The test compound has a moderate antimicrobial activity and the optimized molecular structure of the studied compound using B3LYP/6-31G (d,p) method showed good agreement with the reported x-ray structure.Keywords: Isoindoline-1, 3-dione, X-ray analysis, Density function theory, Antimicrobial, Molecular dockin

5-Bromo-4-(3,4-dimeth­oxy­phen­yl)thia­zol-2-amine

In the title compound, C11H11BrN2O2S, the thia­zole ring makes a dihedral angle of 53.16 (11)° with the adjacent benzene ring. The two meth­oxy groups are slightly twisted from the attached benzene ring with C—O—C—C torsion angles of −9.2 (3) and −5.5 (3)°. In the crystal, mol­ecules are linked by a pair of N—H⋯N hydrogen bonds into an inversion dimer with an R 2 2(8) ring motif. The dimers are further connected by N—H⋯O hydrogen bonds into a tape along [-110]

1-(4-Fluoro­phen­yl)-2-(phenyl­sulfon­yl)ethanone

In the title compound, C14H11FO3S, the unit comprising the ethanone and 4-fluoro­phenyl groups is essentially planar, with an r.m.s. deviation of 0.0084 (2) Å for the ten non-H atoms, and it makes a dihedral angle of 37.31 (10)° with the phenyl ring. In the crystal, mol­ecules are linked by pairs of weak C—H⋯O hydrogen bonds into inversion dimers with R 2 2(16) graph-set motifs. The dimers are stacked along the b axis through further C—H⋯O hydrogen bonds

3-Methyl-1-benzofuran-2-carbohydrazide

In the asymmetric unit of the title benzofuran derivative, C10H10N2O2, there are three crystallograpically independent mol­ecules, which are slightly twisted; the dihedral angle between the benzofuran ring system and the plane of the carbohydrazide unit is 8.64 (11)° in one mol­ecule, whereas the dihedral angles are 9.58 (11) and 6.89 (10)° in the other two mol­ecules. In the crystal, the three independent mol­ecules are linked to each other through N—H⋯N hydrogen bonds, forming a trimer. The trimers are further linked by weak N—H⋯O and C—H⋯O hydrogen bonds into a three-dimensional network. π–π inter­actions with centroid–centroid distances in the range 3.4928 (11)–3.8561 (10) Å are also observed

Synthesis, characterization, x-ray structure and antimicrobial activity of N-(4-chlorophenyl)-2-(pyridin-4- ylcarbonyl) hydrazinecarbothioamide

Purpose: To synthesize thiosemicarbazide and determine its antimicrobial properties.Methods: Pyridine-based thiosemicarbazide was synthesized, characterized and evaluated for antimicrobial activity. The structure of the synthesized compound was established by spectral analysis, namely, Fourier transform infrared spectroscopy (FT-IR), proton nuclear magnetic resonance spectroscopy (1H NMR), carbon 13 magnetic resonance spectroscopy (13C NMR), liquid chromatography-mass spectroscopy (LC-MS), single crystal x-ray analysis as well as by elemental analysis.Results: The title compound crystallized in monoclinic form with space group P21/c of a = 11.6050 (3) Å, b = 13.3130 (4) Å, c = 9.9884 (3) Å, β = 94.911 (2)°, V = 1537.52 (8) Å3, Z = 4 and Rint = 0.033. The pyridine ring formed dihedral angles of 74.1(3) and 88.2(5)° with major and minor components of disordered benzene ring, respectively. In the crystal packing, molecules were linked via intermolecular N—H•••N, N—H•••S and N—H•••O hydrogen bonds into zigzag layers. Compound 2 was most effective against Bacillus subtilis ATCC 10400, MRSA 85N, MRSA 66N and MRSA 15G, compared to the reference drugs, ampicillin and ceftriaxone.Conclusion: The title compound represents a good lead for the development of potent antibacterial agent against Gram positive bacteria and MRSA strains.Keywords: Isoniazid, Thiosemicarbazide, Single crystal x-ray, Antimicrobial activit

X-ray Molecular Structure of ({[(1E)-3-(1H-Imidazol-1-yl)-1- phenylpropylidene]amino} oxy)(3,4,5-trimethoxyphenyl)- methanone: A Potential Anti-Candida Agent

Purpose: To elucidate the solid-state conformation as well as the imine double bond configuration of a potential anti-Candida agent ({[(1E)-3-(1H-imidazol-1-yl) 1-phenylpropylidene]amino}oxy)(3,4,5- trimethoxyphenyl)methanone.Methods: Acetophenone was used as a starting material to prepare the target oximino ester in a fourstep reaction sequence. Nuclear magnetic resonance (1H-NMR and 13C-NMR) and mass spectrometry were used to confirm the chemical structure of the synthesized compounds. Thereafter, x-ray crystallography was performed on single crystals of the target compound. The solid-state conformation of the target molecule and the (E)-configuration of its imine double bond were determined via the investigation of its single crystal x-ray molecular structure.Results: The titled compound crystallized in the triclinic space group P-1 with a = 11.0719 (7) Å, b = 14.6602 (9) Å, c = 14.8530 (9) Å, α = 67.205 (4)°, β = 80.388 (5)º, γ = 70.100 (5)°, V = 2088.2 (2) Å3, and Z = 4. Individual molecules were packed in the crystal by three weak non-classical intermolecular hydrogen interactions, including C9A—H9AA•••O3A, C9B—H9BA•••O3B, C18B—H18C•••O2A and C20B—H20B•••O4B.Conclusion: The results of the single crystal x-ray molecular structure of the titled anti-Candida agent unequivocally confirmed its (E)-configuration.Keywords: Molecular structure, X-ray crystallography, Synthesis, Azole, Anti-Candid

Single-Crystal X-ray Structure of Anti-Candida Agent, (E)-3- (1H-Imidazol-1-yl)-1-Phenylpropan-1-one O-3- Chlorobenzoyl Oxime

Purpose: To determine the conformation as well as imine double bond configuration of the anti- Candida oximino ester, 3-(1H-imidazol-1-yl)-1-phenyl- propan-1-one O-3-chlorobenzoyl oxime.Methods: The titled compound was synthesized in a four-step reaction sequence using acetophenone as a starting material. Spectral analysis, viz, nuclear magnetic resonance (1H NMR and 13C NMR spectroscopy) and mass spectrometry (MS) confirmed the chemical structure of the synthesized compounds. Subsequently, single crystals of the titled compound were subjected to x-ray crystallographic analysis.Results: The single crystal x-ray crystallography of the investigated anti-Candida agent revealed its conformation and the (E)-configuration of its imine double bond. The titled compound crystallizes in the monoclinic space group P21/c with a = 11.1894 (2)Å, b = 19.5577 (4)Å, c = 8.2201 (2)Å, β = 104.919 (2)º, V = 1738.24 (6)Å3, Z = 4. The molecules are packed in crystal structure by weak non-classical intermolecular hydrogen C2—H2A•••O2 interactions.Conclusion: X-ray crystallography analysis confirms the (E)-configuration of the titled compound.Keywords: X-ray crystallography, Synthesis, Anti-Candida, Configuration, Conformation, Single crysta

1-(5-Bromo-4-phenyl-1,3-thia­zol-2-yl)pyrrolidin-2-one

The asymmetric unit of the title compound, C13H11BrN2OS, consists of two crystallographically independent mol­ecules (A and B). In each mol­ecule, the pyrrolidine ring adopts an envelope conformation with a methyl­ene C atom as the flap atom. In mol­ecule A, the central thia­zole ring makes a dihedral angle of 36.69 (11)° with the adjacent phenyl ring, whereas the corresponding angle is 36.85 (12)° in mol­ecule B. The pyrrolidine ring is slightly twisted from the thia­zole ring, with C—N—C—N torsion angles of 4.8 (3) and 3.0 (4)° in mol­ecules A and B, respectively. In the crystal, C—H⋯π and π–π [centroid-to-centroid distance = 3.7539 (14) Å] inter­actions are observed. The crystal studied was a pseudo-merohedral twin with twin law (-100 0-10 101) and a refined component ratio of 0.7188 (5):0.2812 (5)