A convenient two-step preparation of NH-free 5-aryl-pyrrole-2-carboxylates is described. The synt... more A convenient two-step preparation of NH-free 5-aryl-pyrrole-2-carboxylates is described. The synthetic route consists of catalytic borylation of commercially available pyrrole-2-carboxylate ester followed by Suzuki coupling without going through pyrrole N–H protection and deprotection steps. The resulting 5-aryl substituted pyrrole-2-carboxylates were synthesized in good- to excellent yields. This synthetic route can tolerate a variety of functional groups including those with acidic protons on the aryl bromide coupling partner. This methodology is also applicable for cross-coupling with heteroaryl bromides to yield pyrrole-thiophene, pyrrole-pyridine, and 2,3’-bi-pyrrole based bi-heteroaryls.
Borylated aryl alkynes have been synthesized via one-pot iridium catalyzed C–H borylation (CHB)/S... more Borylated aryl alkynes have been synthesized via one-pot iridium catalyzed C–H borylation (CHB)/Sonogashira cross-coupling of aryl bromides. Direct borylation of aryl alkynes encountered problems related to the reactivity of the alkyne under CHB conditions. However, tolerance of aryl bromides to CHB made possible a subsequent Sonogashira cross-coupling to access the desired borylated aryl alkynes.
Biarylboronic esters are generally prepared by directed ortho-metalation or by Miyaura borylatio... more Biarylboronic esters are generally prepared by directed ortho-metalation or by Miyaura borylation and hence rely on the presence of a directing group or pre-functionalization. In this paper, the preparation of biarylboronic esters by direct C–H borylation of biaryl substrates is reported. Sterically governed regioselectivities were observed in the borylation of appropriately substituted biaryls by using [Ir(OMe)(COD)]2 precatalyst and di-tert-butylbipyridyl ligand. The resulting biarylboronic esters were isolated in 38–98% yields. The synthesized biarylboronic esters were further successfully employed in C–O, C–Br, and C–C coupling reactions.
We have carried out a docking inspired synthesis and screening of a library of diazenyl-derivativ... more We have carried out a docking inspired synthesis and screening of a library of diazenyl-derivatives of pyridazinylpyrazolone molecules for their ability to modulate the amyloidogenic self-assembly of human islet amyloid polypeptide (hIAPP). hIAPP is a 37-residue peptide which is involved in glycemic control along with insulin. Its extracellular fibrillar assemblies in pancreatic β-cells are responsible for type 2 diabetes. A three-step synthetic scheme was used to prepare these novel compounds using 2-(6-chloropyridazin-3-yl)-5-methyl-2,4-dihydro-3H-pyrazol-3-one as a key intermediate that was reacted with various diazo electrophiles to generate a library of compounds with yields ranging from 64 to 85%. The effect of the compounds on hIAPP amyloid fibril formation was evaluated with a thioflavin T (ThT) fluorescence-based kinetic assay. Furthermore, TEM imaging was carried out to corroborate the interactions of the compounds with hIAPP and subsequent hIAPP inhibition at the different level of fibrillization. The CD spectroscopy showed that upon incubation with SSE15314 for 12 h, the percentage of α-helices was maintained to a level of hIAPP at 0 h. The current study presents identification and characterization of SSE15314 as the hit, which completely inhibited the fibril formation and can be further optimized into a lead compound.
Environmental science and pollution research international, 2018
The present study focused on exploring the potential of Ag-ZnO composites for complete mineraliza... more The present study focused on exploring the potential of Ag-ZnO composites for complete mineralization of imidacloprid with the aim to sustain the pollutant free safe water supply. The composites were prepared by hydrothermal method and characterized by Scanning electron microscope (SEM), Energy dispersive X-ray crystallography (EDX), X-ray diffraction (XRD) and band gap measurements. These composites were used to study the UV irradiated degradation of imidacloprid while optimizing the process parameters such as time of UV irradiation, pH of medium, pesticide concentration and composite loading. The results of the study revealed an increase in photodegradation of imidacloprid by Ag-ZnO composites than pure ZnO. Temperature and catalyst loading had a positive effect on degradation efficiency, while an inverse relation was observed between pesticide concentration and degradation. Moreover, no harmful degradation products of imidacloprid were observed in GC-MS analyses that confirmed it...
Tumor suppressor protein p53 induces cell cycle arrest and apoptotic cell death in response to va... more Tumor suppressor protein p53 induces cell cycle arrest and apoptotic cell death in response to various cellular stresses thereby preventing cancer development. Activation and stabilization of p53 through small organic molecules is, therefore, an attractive approach for the treatment of cancers retaining wild-type p53. In this context, a series of nineteen chalcones with various substitution patterns of functional groups including chloro, fluoro, methoxy, nitro, benzyloxy, 4-methyl benzyloxy was prepared using Claisen-Schmidt condensation. The compounds were characterized using NMR, HRMS, IR and melting points. Evaluation of synthesized compounds against human colorectal (HCT116) and breast (CAL-51) cancer cell lines revealed potent antiproliferative activities. Nine compounds displayed GI50 values in the low micromolar to submicromolar range; for example (E)-1-phenyl-3-(3,4,5-trimethoxyphenyl)prop-2-en-1-one (SSE14108) showed GI50 of 0.473±0.043µM against HCT116 cells. Further analy...
The present study describes several novel 2,5-biaryl-3-hexylthiophene derivatives (3a-i) synthesi... more The present study describes several novel 2,5-biaryl-3-hexylthiophene derivatives (3a-i) synthesized via a Pd(0)-catalyzed Suzuki cross-coupling reaction in moderate to good yields. The novel compounds were also analyzed for their anti-thrombolytic, haemolytic, and biofilm inhibition activities. In addition, the anti-tumor activity was also evaluated in vitro for newly-synthesized compounds, where 3-hexyl-2,5-bis(4-(methylthio)phenyl)thiophene exhibited the best anti-tumor activity against 4T1 cells with IC50 value of 16 μM. Moreover, 2,5-bis(4-methylphenyl)-3-hexylthiophene showed the highest activity against MCF-7 cells with an IC50 value of 26.2 μM. On the other hand, the compound 2,5-bis(4-chloropheny)-3-hexylthiophene exhibited excellent biofilm inhibition activity. Furthermore, the compound 2,5-bis(3-chloro-4-fluorophenyl)-3-hexylthiophene also exhibited better anti-thrombolytic and hemolytic activity results as compared to the other newly-synthesized compounds.
Agricultural soils contain both heavy metals and pesticides originating from various agricultural... more Agricultural soils contain both heavy metals and pesticides originating from various agricultural practices. It is quite important to study the relationships between these two classes of compounds. To accomplish this, 52 soil samples were collected from cotton fields and analyzed for their metal contents (Ni, Cu, Co, Pb, Cr, and Cd) and levels of most commonly used pesticides (imidacloprid, acetamiprid, and emamectin). FAAS was used for metal estimation and the pesticides were determined by HPLC equipped with UV detector. The results of the study revealed slightly enhanced levels of Ni and Cd in these samples while the rest of the metals were present within tolerable range. Acetamiprid residues in soil were strongly positively correlated with Cu and negatively correlated with Cr. Similarly, imidacloprid in soil was negatively correlated with Ni. Thus it was evidenced that Cu stabilizes acetamiprid while Cr and Ni facilitate the degradation of acetamiprid and imidacloprid in the soil.
A convenient two-step preparation of NH-free 5-aryl-pyrrole-2-carboxylates is described. The synt... more A convenient two-step preparation of NH-free 5-aryl-pyrrole-2-carboxylates is described. The synthetic route consists of catalytic borylation of commercially available pyrrole-2-carboxylate ester followed by Suzuki coupling without going through pyrrole N–H protection and deprotection steps. The resulting 5-aryl substituted pyrrole-2-carboxylates were synthesized in good- to excellent yields. This synthetic route can tolerate a variety of functional groups including those with acidic protons on the aryl bromide coupling partner. This methodology is also applicable for cross-coupling with heteroaryl bromides to yield pyrrole-thiophene, pyrrole-pyridine, and 2,3’-bi-pyrrole based bi-heteroaryls.
Borylated aryl alkynes have been synthesized via one-pot iridium catalyzed C–H borylation (CHB)/S... more Borylated aryl alkynes have been synthesized via one-pot iridium catalyzed C–H borylation (CHB)/Sonogashira cross-coupling of aryl bromides. Direct borylation of aryl alkynes encountered problems related to the reactivity of the alkyne under CHB conditions. However, tolerance of aryl bromides to CHB made possible a subsequent Sonogashira cross-coupling to access the desired borylated aryl alkynes.
Biarylboronic esters are generally prepared by directed ortho-metalation or by Miyaura borylatio... more Biarylboronic esters are generally prepared by directed ortho-metalation or by Miyaura borylation and hence rely on the presence of a directing group or pre-functionalization. In this paper, the preparation of biarylboronic esters by direct C–H borylation of biaryl substrates is reported. Sterically governed regioselectivities were observed in the borylation of appropriately substituted biaryls by using [Ir(OMe)(COD)]2 precatalyst and di-tert-butylbipyridyl ligand. The resulting biarylboronic esters were isolated in 38–98% yields. The synthesized biarylboronic esters were further successfully employed in C–O, C–Br, and C–C coupling reactions.
We have carried out a docking inspired synthesis and screening of a library of diazenyl-derivativ... more We have carried out a docking inspired synthesis and screening of a library of diazenyl-derivatives of pyridazinylpyrazolone molecules for their ability to modulate the amyloidogenic self-assembly of human islet amyloid polypeptide (hIAPP). hIAPP is a 37-residue peptide which is involved in glycemic control along with insulin. Its extracellular fibrillar assemblies in pancreatic β-cells are responsible for type 2 diabetes. A three-step synthetic scheme was used to prepare these novel compounds using 2-(6-chloropyridazin-3-yl)-5-methyl-2,4-dihydro-3H-pyrazol-3-one as a key intermediate that was reacted with various diazo electrophiles to generate a library of compounds with yields ranging from 64 to 85%. The effect of the compounds on hIAPP amyloid fibril formation was evaluated with a thioflavin T (ThT) fluorescence-based kinetic assay. Furthermore, TEM imaging was carried out to corroborate the interactions of the compounds with hIAPP and subsequent hIAPP inhibition at the different level of fibrillization. The CD spectroscopy showed that upon incubation with SSE15314 for 12 h, the percentage of α-helices was maintained to a level of hIAPP at 0 h. The current study presents identification and characterization of SSE15314 as the hit, which completely inhibited the fibril formation and can be further optimized into a lead compound.
Environmental science and pollution research international, 2018
The present study focused on exploring the potential of Ag-ZnO composites for complete mineraliza... more The present study focused on exploring the potential of Ag-ZnO composites for complete mineralization of imidacloprid with the aim to sustain the pollutant free safe water supply. The composites were prepared by hydrothermal method and characterized by Scanning electron microscope (SEM), Energy dispersive X-ray crystallography (EDX), X-ray diffraction (XRD) and band gap measurements. These composites were used to study the UV irradiated degradation of imidacloprid while optimizing the process parameters such as time of UV irradiation, pH of medium, pesticide concentration and composite loading. The results of the study revealed an increase in photodegradation of imidacloprid by Ag-ZnO composites than pure ZnO. Temperature and catalyst loading had a positive effect on degradation efficiency, while an inverse relation was observed between pesticide concentration and degradation. Moreover, no harmful degradation products of imidacloprid were observed in GC-MS analyses that confirmed it...
Tumor suppressor protein p53 induces cell cycle arrest and apoptotic cell death in response to va... more Tumor suppressor protein p53 induces cell cycle arrest and apoptotic cell death in response to various cellular stresses thereby preventing cancer development. Activation and stabilization of p53 through small organic molecules is, therefore, an attractive approach for the treatment of cancers retaining wild-type p53. In this context, a series of nineteen chalcones with various substitution patterns of functional groups including chloro, fluoro, methoxy, nitro, benzyloxy, 4-methyl benzyloxy was prepared using Claisen-Schmidt condensation. The compounds were characterized using NMR, HRMS, IR and melting points. Evaluation of synthesized compounds against human colorectal (HCT116) and breast (CAL-51) cancer cell lines revealed potent antiproliferative activities. Nine compounds displayed GI50 values in the low micromolar to submicromolar range; for example (E)-1-phenyl-3-(3,4,5-trimethoxyphenyl)prop-2-en-1-one (SSE14108) showed GI50 of 0.473±0.043µM against HCT116 cells. Further analy...
The present study describes several novel 2,5-biaryl-3-hexylthiophene derivatives (3a-i) synthesi... more The present study describes several novel 2,5-biaryl-3-hexylthiophene derivatives (3a-i) synthesized via a Pd(0)-catalyzed Suzuki cross-coupling reaction in moderate to good yields. The novel compounds were also analyzed for their anti-thrombolytic, haemolytic, and biofilm inhibition activities. In addition, the anti-tumor activity was also evaluated in vitro for newly-synthesized compounds, where 3-hexyl-2,5-bis(4-(methylthio)phenyl)thiophene exhibited the best anti-tumor activity against 4T1 cells with IC50 value of 16 μM. Moreover, 2,5-bis(4-methylphenyl)-3-hexylthiophene showed the highest activity against MCF-7 cells with an IC50 value of 26.2 μM. On the other hand, the compound 2,5-bis(4-chloropheny)-3-hexylthiophene exhibited excellent biofilm inhibition activity. Furthermore, the compound 2,5-bis(3-chloro-4-fluorophenyl)-3-hexylthiophene also exhibited better anti-thrombolytic and hemolytic activity results as compared to the other newly-synthesized compounds.
Agricultural soils contain both heavy metals and pesticides originating from various agricultural... more Agricultural soils contain both heavy metals and pesticides originating from various agricultural practices. It is quite important to study the relationships between these two classes of compounds. To accomplish this, 52 soil samples were collected from cotton fields and analyzed for their metal contents (Ni, Cu, Co, Pb, Cr, and Cd) and levels of most commonly used pesticides (imidacloprid, acetamiprid, and emamectin). FAAS was used for metal estimation and the pesticides were determined by HPLC equipped with UV detector. The results of the study revealed slightly enhanced levels of Ni and Cd in these samples while the rest of the metals were present within tolerable range. Acetamiprid residues in soil were strongly positively correlated with Cu and negatively correlated with Cr. Similarly, imidacloprid in soil was negatively correlated with Ni. Thus it was evidenced that Cu stabilizes acetamiprid while Cr and Ni facilitate the degradation of acetamiprid and imidacloprid in the soil.
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