A new synthesis and stereocontrolled functionalization of substituted silacyclopent-3-enes

C2-Substituted silacyclopent-3-enes have been prepared in good yields in two steps starting from commercially available diallylsilane 9. Coupling between carbanion of 9 and aldehydes or epoxides followed by ring-closing metathesis of the corresponding substituted diallylsilanes led to various silacyclopent-3-enes having a beta- or a gamma-hydroxysilane moiety. Dihydroxylation and epoxidation of the sila-cycle then led stereoselectively to polyhydroxylated silacyclopentanes. These processes were shown to occur with opposite topicity, offering a complementary and stereocontrolled access to diastereomeric polyols having up to five contiguous stereogenic centers.     

Effect of hydrolysis on the yield of hederagenin and High-performance thin-layer chromatography densitometric quantification of hederagenin in fruit pericarp of Sapindus spp

Fruit pericarp of Sapindus species are reported to contain glycosides with hederagenin as an aglycone. To free the aglycone from the glycosides, they need to be hydrolyzed, and the commonly used method is hydrolysis with either hydrochloric or sulfuric acid. In the present work, we studied the effect of hydrolysis on the yield of hederagenin from the fruit pericarp of 3 species of Sapindus, viz., S. mukorossi, S. laurifolius, and S. emarginatus. A high-performance thin-layer chromatography densitometric method for the quantification of hederagenin was developed and validated. It involved automated application of samples as bands onto silica gel 60F254 plates, development with toluene-ethyl acetate-formic acid (7 + 3 + 5, v/v/v) mobile phase, detection with anisaldehyde-sulfuric acid reagent, and scanning at 595 nm. The yield of hederagenin ranged from 0.035 to 1.29% (w/w) with different methods of hydrolysis. Hydrolysis with 3.5 M aqueous sulfuric acid under reflux for 6 h gave the maximum yield of hederagenin in all 3 species, with the highest amount in S. emarginatus (1.29%, w/w).     

Simultaneous Quantification of Three Bioactive Lignans,viz., Phyllanthin,Hypophyllanthin, and Niranthin from Phyllanthus amarus Using High-Performance Thin-Layer Chromatography

JPC – Journal of Planar Chromatography – Modern TLC - Phyllanthus amarus, a well-known drug of the Indian Systems of Medicine, possesses a wide variety of pharmacological activities...     

Simultaneous Quantification of Picrosides I and II from Picrorhiza kurroa,Picrolax Capsules,and Picrolax Suspension: High-Performance Thin-Layer Chromatographic-Densitometric Method Developed with Kutkin

JPC – Journal of Planar Chromatography – Modern TLC - Kutkin, a mixture of two iridoid glycosides, viz., picrosides I and II, is a major active constituent of Picrorhiza kurroa (family:...     

New class of biodegradable polymers formed from reactions of an inorganic functional group

Although numerous small molecules have been synthesized with sulfenamide bonds (R(2)N-SR), this is the first report of the synthesis of polysulfenamides. These polymers are readily synthesized at room temperature using secondary diamines and dithiosuccinimides. The dithiosuccinimides were readily synthesized in one step by the reaction of dithiols such as HS(CH(2))(6)SH with N-chlorosuccinimide. The resulting dithiosuccinimides were either recrystallized or readily purified by chromatography on silica gel and required no special handling. The conversions of polymerization ranged from 95 to 98%, and the molecular weights of the polymer reached as high as 6,300 g mol(-1). The sulfenamide bond was very stable in organic solvents, and no degradation was observed under atmospheric conditions in C(6)D(6) for 30 days. In contrast, the sulfenamide bond readily decomposed in less than 12 h in D(2)O. Polysulfenamides were fabricated into micron-sized particles loaded with dye and endocytosed into JAWSII immature dendritic and HEK293 cells. Polysulfenamides represent a new class of polymers that are readily synthesized, stable in aprotic solvents, and readily degrade in water.     

Structural and electronic properties of sulphur-doped boron nitride nanotubes

First-principles calculations based on density functional theory were performed to study the structural and electronic properties of sulphur substitution-doped boron nitride (BN) nanotubes, using the theory as implemented in SIESTA code, which uses non-conserving pseudo-potentials in fully non-local form and atomic orbitals as the basis set. The generalized gradient approximation (GGA) was used for the exchange–correlation (XC) potential. The tube selected was a (10, 0) BN nanotube that fell in the range of energy gap independent of the tube diameter. The electronic and structural properties for sulphur substitution in the boron and the nitrogen sites were studied. The structural arrangement in equilibrium conditions for S shows an outward radial deformation around the sulphur atom in the tube. The bandgap of the pristine BN nanotubes was found to be significantly modified on doping.     

Facile Synthesis of Pyrazoline Derivatized Amides via Sydnone Ring Cleavage

In the present investigation, we have utilized 3‐[3′‐(5″‐aryl‐2″‐pyrazolin‐3″‐yl)]phenylsydnones 1a–c to couple two biodynamic moieties in amide derivatives 7 , 8 , 9 , 10 . The compounds 1a–c were brominated to 4‐bromo‐3‐[3′‐(5″‐aryl‐2″‐pyrazolin‐3″‐yl)]phenylsydnone 2 , which were further reacted with secondary amines to form the title compounds. These novel molecules were subjected to antitubercular activity against Mycobacterium tuberculae (H₃₇R_v) and antioxidant activity assay.     

Iridoid glycosides-Kutkin,Picroside I,and Kutkoside from Picrorrhiza kurroa Benth inhibits the invasion and migration of MCF-7 breast cancer cells through the down regulation of matrix metalloproteinases: 1st Cancer Update

Ethnopharmacological relevanceIridoid glycosides have been associated with decreased risks of cancer, such as hepatocarcinoma. Although Picrorrhiza kurroa has shown activity against hepatocarcinogenesis, its mechanism of action is poorly understood, further the anticancer activity of iridoid glycosides present in this plant has not been tested so far.Aim of the studyHere, MCF-7 cell lines (Human breast cancer) were used to test whether P. kurroa extract (PE) and its isolated iridoid glycosides Picroside I (PS), Kutkoside (KS), and Kutkin (KT) exerts the anti-invasion activity via down-regulation of the expression of matrix metalloproteinases (MMPs). MMPs play an important role in solid tumor invasion and migration.Materials and methodsThe activity and expression of gelatinases (MMP-2 and MMP-9) and collagenases (MMP-1 and MMP-13), protein, and mRNA were detected by gelatin zymography, and RT-PCR. The migratory and invasive capacities of MCF-7 cell lines were measured by the wound scratch migration assay. The preliminary cytotoxicity testing was done by MTT assay and propidium iodide staining. Further the inhibition of inflammatory mediators was also done by quantification of nitrite inflammatory mediators.ResultsThe study showed that PE and its isolated iridoids glycosides PS, KS, and KT exhibited considerable cytotoxic potential in a dose-dependent manner. Further PE, PS, KS, and KT inhibited MCF-7 cell invasion and migration, and decreased MMP-2, 9 and MMP-1, 13 activities. Furthermore, PS, KS, and KT reduced MMPs expression at protein and mRNA levels, and suppression of the inflammatory mediators was also exhibited.ConclusionsOur results suggest that PS, KS, and KT may be the valuable anti-invasive drug candidates for cancer therapy by suppressing Collagenases and Gelatinases. PS, KS, and KT showed good results in comparison with PE. PS and KS exhibit almost comparable down regulation while KT exhibited maximum suppression of invasion, migration, and expression of MMPs.     

Synthesis and biological evaluation of 16E-arylidenosteroids as cytotoxic and anti-aromatase agents

Taking into consideration the structural requirements for cytotoxicity and aromatase inhibition, several new 16E-arylidenosteroidal derivatives have been prepared and evaluated for their cytotoxic and aromatase inhibitory activity. The new steroidal analogues 3, 5-8 and 11 exhibited significant cytotoxic effects when screened against three cancer cell lines, MCF-7 (breast), NCl-H460 (lung) and SF-268 central nervous system (CNS) at 100 μM and sensible cytotoxic effects subsequently in sixty cancer cell lines derived from nine cancers types (leukemia, lung, colon, CNS, melanoma, ovarian, renal, prostate and breast cancers). The imidazolyl substituted steroidal derivatives 5 and 7 exhibited strong inhibition of the aromatase enzyme with 16-[4-{3-(imidazol-1-yl)propoxy}-3-methoxybenzylidene]-5-androstene-3β,17β-diol (7) displaying 13 times more potency in comparison to aminoglutethimide.     

Tuning the Photometric Properties of Ternary Sm3+ Complexes Involving Mixed-Ligands

This research article deals with the synthesis of ternary Sm³⁺ complexes with 6,8-dichlorochromone-3-carboxaldehyde through solution-precipitation method. The photometric properties of resultant complexes were tuned by coordinating N-donor heterocyclic ligands with Sm³⁺ ion. The emission spectra, obtained in the visible region have been studied. Under optical excitation of 370 nm, the complexes displayed characteristic Sm³⁺-centered emission peaks at?~?563, 600 and 647 nm in solution as well as in powder state. The complexes showed thermal stability up to 175 °C. The complexes delivered quantum yield as high as 7.91% and longest emission lifetime of 0.564 ms. The color coordinates of the complexes, located in deep orange (in solution) and red (in powder) spectral region, matched well with the Society of Motion Picture and Television Engineers and European Broadcasting Union. The properties of complexes have been investigated to a significant extent due to their easy synthesis and potential applications as orange-red light emitter in a wide range of photonic applications such as display devices, OLEDs, dashboards, optical systems.