Crystal structure of 3-(adamantan-1-yl)- 4-(4-chlorophenyl)-1H-1,2,4-triazole- 5(4H)-thione

The title compound, C18H20ClN3S, is a functionalized triazoline- 3-thione derivative. The benzene ring is almost perpendicular to the planar 1,2,4-triazole ring [maximum deviation = 0.007 (1) A ° ] with a dihedral angle of 89.61 (5)� between them and there is an adamantane substituent at the 3-position of the triazolethione ring. In the crystal, N—H� � �S hydrogenbonding interactions link the molecules into chains extending along the c-axis direction. The crystal packing is further stabilized by weak C—H� � �� interactions that link adjacent chains into a two-dimensional structure in the bc plane. The crystal studied was an inversion twin with a 0.50 (3):0.50 (3) domain ratio

Anti-Inflammatory Screening and Molecular Modeling of Some Novel Coumarin Derivatives

Coumarin and their derivatives have drawn much attention in the pharmacological and pharmaceutical fields due to their broad range and diverse biological activities. In the present work, starting from the 6-amino-7-hydroxy-4-methyl-2H-chromen-2-one, a series of 6-(substituted benzylamino)-7-hydroxy-4-methyl-2H-chromen-2-ones 1–11 was synthesized and assessed for their anti-inflammatory activity using the carrageenan-induced hind paw edema method. Compounds 2, 3, 4 and 9 showed significant (p < 0.001) reduction of rat paw edema volume after 1 h from the administration of the carrageenan compared to the reference drug, indomethacin. On the other hand, compounds 4 and 8 showed the highest anti-inflammatory activity, surpassing indomethacin after 3 h with 44.05% and 38.10% inhibition, respectively. Additionally, a molecular docking study was performed against the COX enzyme using the MOE 10.2010 software

Synthesis, structure elucidation, and antifungal potential of certain new benzodioxole–imidazole molecular hybrids bearing ester functionalities

Reem I Al-Wabli,1 Alwah R Al-Ghamdi,1 Hazem A Ghabbour,2 Mohamed H Al-Agamy,3,4 Mohamed I Attia1,5 1Department of Pharmaceutical Chemistry, College of Pharmacy, King Saud University, Riyadh 11451, Saudi Arabia; 2Department of Medicinal Chemistry, Faculty of Pharmacy, Mansoura University, Mansoura 35516, Egypt; 3Department of Pharmaceutics, College of Pharmacy, King Saud University, Riyadh 11451, Saudi Arabia; 4Microbiology and Immunology Department, Faculty of Pharmacy, Al-Azhar University, Cairo 11884, Egypt; 5Medicinal and Pharmaceutical Chemistry Department, Pharmaceutical and Drug Industries Research Division, National Research Centre, Dokki, Giza 12622, Egypt Background: The incidence of fungal infections is a growing serious global health burden. There is an urgent medical demand to acquire new antifungal drug-like compounds having azole nuclei to get rid of the drawbacks of the currently available azole antifungal agents. Methods: The target compounds 5a-r were synthesized in a four-step reaction sequence using the appropriate acetophenone derivative as a starting material. The antifungal potential of the title compounds was assessed using DIZ and MIC assays according to the reported standard procedures. Results: The newly synthesized oximino esters 5a-r were identified with the aid of various spectroscopic approaches. Their assigned chemical structures were confirmed via single-crystal X-ray structure of compound 5o. The molecular structure of compound 5o was crystallized in the triclinic, P-1, a=9.898 (3) Å, b=10.433 (3) Å, c=11.677 (4) Å, α=86.886 (6)°, β=87.071 (7)°, γ=64.385 (6)°, V=1,085.2 (6) Å3, Z=2. The synthesized compounds 5a-r were in vitro evaluated for antifungal potential against four fungal strains. Compounds 5l and 5m bearing a trifluoromethylphenyl moiety showed the best anti-Candida albicans activity with minimum inhibitory concentration (MIC) value of 0.148 µmol/mL, while compound 5b displayed the best activity toward Candida tropicalis with MIC value of 0.289 µmol/mL. Compounds 5o and 5l were the most active congeners against Candida parapsilosis and Aspergillus niger, respectively. Conclusion: Single-crystal X-ray analysis of compound 5o confirmed without doubt the assigned chemical structures of the title compounds as well as confirmed the (E)-configuration of their oximino group. Compounds 5b, 5l, 5m, and 5o emerged as the most active compounds against the tested fungi and they could be considered as new antifungal lead candidates. Keywords: crystal structure, imidazole, benzodioxole, ester, antifunga

Synthesis of curcumin and ethylcurcumin bioconjugates as potential antitumor agents

We appreciate very much the help of Dr. Abeer El-Alfy, Pharmacology Department, King Saud University and Dr. Shabana Khan, National center for Natural Products Research, University of Mississipi, USA, for performing the Cytotoxicity Tests.Some new curcumin and ethylcurcumin bioconjugates with various functionalities supported on the curcumin skeleton were synthesized and evaluated for antitumor activity. Most of the newly synthesized compounds are more active than curcumin and ethyl curcumin but are less cytotoxic than the reference compound doxorubicin. Surprisingly, many of these compounds are not cytotoxic to noncancer cells. Compounds 5c, 5e, 5g, 5j, 6b, and 6g having 5-methylthiadiazole, 6-methoxy-benzothiazole, diethylaminoethyl and the usual alkylating bis(2chloroethyl)amino moieties showed the highest cytotoxic activity against SK-MEL cancer cells. Compounds 5k, 6c, and 6g are less cytotoxic to KB cancer cells. Moreover, compounds 5c, 5e, 5j, 5k, 6d, 6e, 6f, and 6g showed cytotoxicity against BT-549 cancer cells with 5j being the most active compound. Curcumin and the new intermediate di-O-chloroacetylcurcumin (3a) were also cytotoxic against the same cell line but are less active than the target compounds. Compound 6b is the only one exhibiting cytotoxicity against SK-OV-3 cancer cells.Springer Scienc

3-Ethoxymethyl-1,4-dihydroquinolin-4-one

In the title molecule, C12H13NO2, the dihydroquinolinone fused-ring system is nearly planar [maximum deviation = 0.012 (3) Å], and the mean plane passing through the extended ethoxymethyl substituent is aligned at 86.9 (2)° with respect to the fused-ring system. In the crystal, adjacent molecules are linked by an N—H...Ocarbonyl hydrogen bond to generate a chain running along the b-axis direction

Synthesis, Spectroscopic Characterization and Antimicrobial Potential of Certain New Isatin-Indole Molecular Hybrids

Molecular hybridization has a wide application in medicinal chemistry to obtain new biologically active compounds. New isatin-indole molecular hybrids 5a–n have been synthesized and characterized by various spectroscopic tools. The in vitro antimicrobial potential of the prepared compounds 5a–n was assessed using diameter of the inhibition zone (DIZ) and minimum inhibitory concentration (MIC) assays against a panel of Gram-negative bacteria, Gram-positive bacteria and fungi. Most of the synthesized compounds 5a–n showed weak activities against Gram-negative bacteria while compounds 5b and 5c exhibited good activities against Gram-positive bacteria. On the other hand, compound 5j emerged as the most active compound towards Candida albicans (C. albicans), with an MIC value of 3.9 µg/mL, and compound 5g as the most active congener towards Asperagillus niger (A. niger), with an MIC value of 15.6 µg/mL. Moreover, compound 5h manifested the best anti-P. notatum effect, with an MIC value of 7.8 µg/mL, making it equipotent with compound 5g

Synthesis and Spectroscopic Identification of Certain Imidazole-Semicarbazone Conjugates Bearing Benzodioxole Moieties: New Antifungal Agents

During the last three decades the extent of life-threatening fungal infections has increased remarkably worldwide. Synthesis and structure elucidation of certain imidazole-semicarbazone conjugates 5a–o are reported. Single crystal X-ray analysis of compound 5e unequivocally confirmed its assigned chemical structure and the (E)-configuration of its imine double bond. Compound 5e crystallized in the triclinic system, P-1, a = 6.3561 (3) Å, b = 12.5095 (8) Å, c = 14.5411 (9) Å, α = 67.073 (4)°, β = 79.989 (4)°, γ =84.370 (4)°, V = 1048.05 (11) Å3, Z = 2. In addition, DIZ and MIC assays were used to examine the in vitro antifungal activity of the title conjugates 5a–o against four fungal strains. Compound 5e, bearing a 4-ethoxyphenyl fragment, showed the best MIC value (0.304 µmol/mL) against both C. tropicalis and C. parapsilosis species, while compounds 5c (MIC = 0.311 µmol/mL), 5k, and 5l (MIC = 0.287 µmol/mL) exhibited the best anti-C. albicans activity

A combined experimental and theoretical study on vibrational and electronic properties of (5-methoxy-1H-indol-1-yl)(5-methoxy-1H-indol-2-yl)methanone

(5-Methoxy-1H-indol-1-yl)(5-methoxy-1H-indol-2-yl)methanone (MIMIM) is a bis-indolic derivative that can be used as a precursor to a variety of melatonin receptor ligands. In this work, the energetic and spectroscopic profiles of MIMIM were studied by a combined DFT and experimental approach. The IR, Raman, UV-Vis, 1H NMR and 13C NMR spectra were calculated by PBEPBE and B3LYP methods, and compared with experimental ones. Results showed good agreement between theoretical and experimental values. Mulliken population and natural bond orbital analysis were also performed by time-dependent DFT approach to evaluate the electronic properties of the title molecule