Synthesis of spirooxindolocarbamates based on Betti reaction: antibacterial,antifungal and antioxidant activities

Molecular Diversity - A series of new spirooxindolocarbamates 4a–l and 6a–d were synthesized by using the Betti reaction. All the target compounds were well characterized by IR, NMR and...     

Crystal Structure Analysis of Betti Base 1-((2-hydroxynaphthalen-1-yl)(2-hydroxyphenyl)methyl)urea•2DMF Solvate

A novel Betti base compound, 1-((2-hydroxynaphthalen-1-yl)(2-hydroxyphenyl)methyl)urea, UBB, was synthesized and characterized by spectral, structural and thermal studies. Single crystal X-ray diffraction studies reveal that the racemic mixture of the compound, when crystallized from DMF, yields R-isomer preferentially (prismatic crystals), whereas, when crystallized from 5:1 (v/v) mixture of DMF-THF, it yields S-isomer (rectangular shaped crystals) with two molecules of DMF, included in both the cases. The crystal structure is discussed in terms of supramolecular interactions and molecular modeling. Both R and S enantiomeric DMF solvate crystals are in their chiral triclinic P1 space group.     

An efficient one-pot synthesis of pyrazolyl-[1,2,4]triazolo[3,4-b][1,3,4] thiadiazin-6-yl)-2H-pyran-2-one derivatives via multicomponent approach and their potential antimicrobial and nematicidal activities

A series of simple or/and aryl, heteryl hydrazono pyrazolyl-[1,2,4]triazolo[3,4-b][1,3,4]thiadiazin-6-yl)-2H-pyran-2-one derivatives have been efficiently synthesized in excellent yields via one-pot, multi-component approach. The importance of this methodology is that in a one-pot operation four new bonds (3C–N and 1C–S) are generated. The structure of compound 5a was confirmed by single-crystal X-ray diffraction. The newly synthesized compounds were evaluated for their in vitro antimicrobial activity against gram-positive bacteria (Staphylococcusaureus and Bacillussubtilis), gram-negative bacteria (Escherichiacoli andKlebsiellapneumoniae), antifungal activity against Candida albicans, and nematicidal activity against Meloidogyneincognita. Among all the compounds 6f showed excellent antimicrobial and nematicidal activity against tested bacteria, fungi, and nematodes.     

Sorting of polymorphs based on mechanical properties. Trimorphs of 6-chloro-2,4-dinitroaniline

Mechanical shearing of crystals of a polymorph with a layered structure may be used to separate them from harder crystals of a visually indistinguishable polymorph that resist such shearing.     

Pharmaceutical Salts of Fluoroquinolone Antibacterial Drugs with Acesulfame Sweetener

Novel organic salts of norfloxacin and ciprofloxacin with artificial sweeteners such as saccharin and acesulfame were prepared. The two salts 1 and 2 were characterized by differential scanning calorimetry (DSC) and powder X-ray diffraction (PXRD). Finally, the crystal structures were solved by single crystal X-ray diffraction data and the structures were analyzed in terms of supramolecular synthons. In norfloxacin acesulfamate 1, two norfloxacin cations and two acesulfame anions form an eight membered cyclic tetramer supramolecular synthon. The salt, ciprofloxacin acesulfamate 2, has a similar structure as salt 1. This study contributes the importance of crystal engineering and supramolecular chemistry to the pharmaceutical applications in terms of interactions and structural correlations in the design of new solid phases.

Supplemental materials are available for this article. Go to the publisher's online edition of Molecular Crystals and Liquid Crystals to view the free supplemental file.     

Synthesis and biological evaluation of new benzo[d][1,2,3]triazol-1-yl-pyrazole-based dihydro-[1,2,4]triazolo[4,3-a]pyrimidines as potent antidiabetic,anticancer and antioxidant agents

Research on Chemical Intermediates - A series of new benzo[d][1,2,3]triazol-1-yl-pyrazole-based dihydro-[1,2,4]triazolo[4,3-a]pyrimidine derivatives 4a-p were synthesized and well characterized by...     

Synthesis of fused thiazolo[3,2-a]pyrimidinones: N-aryl-2-chloroacetamides as doubly electrophilic building blocks

2-Chloro-N-phenylacetamide and N-(benzo[d]thiazol-2-yl)-2-chloroacetamide are doubly electrophilic building blocks for the formation of ring annulated thiazolo[3,2-a]pyrimidinone products. This synthetic route involves formation of the title compound in acceptable product yields by the elimination of the by-product, aniline/2-aminobenzothiazole. Analytical and spectral studies, as well as single crystal X-ray data on the representative compound 6c confirmed the structure of all the reaction products.     

Ultrasound-assisted rapid and efficient one-pot synthesis of furanyl spirooxindolo and spiroquinoxalinopyrrolizidines by 1,3-dipolar cycloaddition: a green protocol

Efficient synthesis of novel spirooxindolo and spiroquinoxalinopyrrolizidine derivatives was expediently accomplished with regioselectivity via one-pot, three-component 1,3-dipolar cycloaddition using ultrasonication. Chalcones derived from both heteroaryl methyl ketones and furfural were used as dipolarophiles in these reactions. The synthesized compounds were analyzed by ¹H and ¹³C nuclear magnetic resonance (NMR), mass spectrometry, and elemental (CHN) analysis. Single-crystal X-ray diffraction studies of one of the compounds (11d) proved the structure and regiochemistry of the cycloaddition. The ultrasound methodology is clearly advantageous, and the desired products were obtained in moderate to good yield in shorter reaction time compared with conventional heating and fusion methods.     

Synthesis and Novel Crystal Structure Analysis of Anthracene-Based Chalcone Derivatives

Abstract

Four novel anthracene-based chalcone derivatives, (E)-1-(anthracen-9-yl)-3-(4-nitrophenyl)prop-2-en-1-one 1, (E)-1-(anthracen-9-yl)-3-(3-chlorophenyl)prop-2-en-1-one 2, (E)-1-(anthracen-9-yl)-3-(3,4,5-trimethoxyphenyl)prop-2-en-1-one 3, and (E)-1-(anthracen-9-yl)-3-(pyridin-4-yl)prop-2-en-1-one four were synthesized and their structures were solved by single crystal X-ray diffraction methods. The anthracenyl chalcone 1 crystallizes in the centrosymmetric monoclinic P2₁/c space group. The crystal structure analysis shows that the molecules of one form two dimensional (2D) corrugated layer structure. The anthracenyl chalcone 2 crystallizes in the centrosymmetric triclinic P-1 space group and forms one dimensional (1D) tape like structure in the crystal. Compound 3 crystallizes in the centrosymmetric monoclinic P2₁/n space group. Anthracenyl chalcone 4 crystallizes in the centrosymmetric triclinic P-1 space group.