Article
Chemistry, Applied
Qingfu Guo, Chunhui Du, Xukun Deng, Yanmei Cheng, Xishi Tai, Guangming Nie
Summary: Novel poly(3,4-dibromothiophene) (PDBrTh) was prepared through electrochemical polymerization using boron trifluoride diethyl etherate (BF3Et2O) as solvent. The PDBrTh showed good electrochemical activity, thermal stability, electrochromic performance, and supercapacitive performance. An all-polythiophenes electrochromic supercapacitor device (ESD) was constructed with PDBrTh, and it exhibited good energy storage property and intelligent visual monitoring of the energy storage state.
Article
Biochemistry & Molecular Biology
Yunyun Zheng, Jiuling Li, Kai Wei
Summary: An efficient, high-yielding, and scalable method for the regioselective 3-acylation of indoles with anhydrides promoted by boron trifluoride etherate under mild conditions was reported. This novel protocol provides a simple way to prepare 3-(benzofuran-2-yl) indole in three steps.
Article
Chemistry, Applied
Tales A. C. Goulart, Ana M. S. Recchi, Davi F. Back, Gilson Zeni
Summary: The Lewis acid-promoted cyclization reaction of benzomidazole thiols with propargyl alcohols for the selective synthesis of benzoimidazolo thiazines and benzothiazolo imidazoles is described. The reaction is regioselective and controlled by the choice of solvent. The best reaction conditions were determined through systematic study, resulting in the formation of six-membered benzoimidazolo thiazines using boron trifluoride etherate and dichloromethane as the solvent, and five-membered benzothiazolo imidazoles using the same starting material and reagents with dimethylformamide as the solvent. The proposed mechanism of the cyclization reaction is based on experimental results and control experiments.
ADVANCED SYNTHESIS & CATALYSIS
(2022)
Review
Chemistry, Medicinal
Guna Sakaine, Anastasija Ture, Julia Pedroni, Gints Smits
Summary: The isolation and evaluation of nearly 60 PBD natural products as potential anticancer agents have led to significant advancements in synthetic studies and total syntheses, culminating in the development of highly potent anticancer agents. This review provides a comprehensive summary of the occurrence and biological activity of PBD natural products, as well as the strategies employed for their total syntheses.
MEDICINAL RESEARCH REVIEWS
(2022)
Article
Chemistry, Organic
Nai-Chen Hsueh, Meng-Yang Chang
Summary: We describe a facile-operational, high-yield method for the diastereocontrolled preparation of novel sulfonyl benzofused fluorooxabicyclo[4.2.1]nonanes by a straightforward synthetic route, including the reduction and intramolecular nucleophilic fluorocyclization. This method allows for the installation of a fluoro-atom on the bridged head position in a short time and under mild conditions, resulting in the formation of one carbon-carbon and one carbon-fluorine bond.
ORGANIC & BIOMOLECULAR CHEMISTRY
(2022)
Article
Chemistry, Organic
Karthikeyan Soundararajan, Helen Ratna Monica Jeyarajan, Raju Subimol Kamarajapurathu, Karthik Krishna Kumar Ayyanoth
Summary: (English Summary)
The chiral (salen)Cr(III)/BF3 center dot OEt2 combination was found to be an effective catalyst for intramolecular Friedel-Crafts cyclization, leading to 2-substituted-1H-indenes from electron-deficient Morita-Baylis-Hillman adducts under mild reaction conditions.
BEILSTEIN JOURNAL OF ORGANIC CHEMISTRY
(2021)
Article
Chemistry, Multidisciplinary
Feng Pan, Haohu Li, Xiaohua Wang, Liwen Luo, Yanfei Lin, Qingkai Yu, Wenlin Xie, Lianpeng Zhang
Summary: A general and convenient protocol for the visible light-promoted radical-mediated cascade spiro-cyclization/Michael addition of N-arylpropiolamides with thiophenols was developed. This method employs commercially available hydrochloric acid as a cheap promoter and air as a sustainable oxidant. The reaction conditions are tolerant towards many functional groups and produce sulfur-containing benzo[b]pyrrolo[2,1-c][1,4]oxazine-3,9-diones.
Review
Chemistry, Organic
Jay Prakash Soni, Nayan Arvind Jadhav, Nagula Shankaraiah
Summary: This review focuses on the azido-reductive cyclization of organic azides and its significant insights. The review elaborates the extensive literature for synthesizing various heterocycles using chemoselective and straightforward protocols for azido-reduction with concomitant intramolecular cyclization. The azido-reductive cyclization strategy has been successfully applied in the synthesis of essential heterocycles and various iminosugars, drugs/APIs, and natural products embedding such heterocycles.
CURRENT ORGANIC CHEMISTRY
(2022)
Article
Chemistry, Multidisciplinary
Vitaly S. Mityanov, Alexandra G. Podrezova, Anton V. Kutasevich, Ivan S. Pytskii, Victor N. Khrustalev
Summary: A new synthetic protocol for the preparation of stable boron trifluoride complexes of oxazole N-oxides has been developed. By condensing alpha-diketone monooximes with an appropriate aldehyde in the presence of equimolar boron trifluoride, a wide range of derivatives including previously unknown 2-unsubstituted oxazole N-oxides can be obtained. The method has been demonstrated to successfully synthesize 25 diverse oxazole derivatives in yields of 14-89%.
Article
Chemistry, Multidisciplinary
Pallavi Singh, Rama Krishna Peddinti
Summary: This paper presents a highly efficient and sustainable synthesis of triarylmethanes through the dehydrative coupling of p-quinols with diaryl carbinols. The catalyst used in this protocol is the in situ generated superacid BF3-H2O from BF3-OEt2. Moisture is used as an efficient initiator in this reaction system, and various diaryl carbinols and p-quinols have been found to be compatible, yielding triarylmethanes with up to 96% yield.
JOURNAL OF CHEMICAL SCIENCES
(2022)
Article
Chemistry, Multidisciplinary
Hongli Chai, Xiang Zhen, Xueqing Wang, Liang Qi, Yuji Qin, Jijun Xue, Zhaoqing Xu, Hongrui Zhang, Weiwei Zhu
Summary: In this study, a hypervalent iodine catalyst was utilized for the nucleophilic fluorination of unsaturated amides, using BF3·Et2O as the fluorine source and activating reagent. Various 5-fluoro-2-oxazoline derivatives were synthesized with good to excellent yields (up to 95% isolated yield) within a short time of 10 minutes. The process was efficient, metal-free, and conducted under mild conditions. A proposed mechanism involving fluorination/1,2-aryl migration/cyclization cascade was based on previous studies and experimental results.
Article
Chemistry, Organic
Zeng Gao, Jinlong Qian, Huameng Yang, Jinlong Zhang, Gaoxi Jiang
Summary: Two approaches involving intramolecular and intermolecular cyclization were developed for the construction of a series of benzo[f]pyrrolo[1,2-a][1,4]azepines using Bronsted acid catalysts. The intramolecular dehydroxylation/ring closure reaction and intermolecular addition reaction both provided high yields of the desired compounds.
Article
Chemistry, Multidisciplinary
Mason T. Koeritz, Haley K. Banovetz, Sean A. Prell, Levi M. Stanley
Summary: This study reports a nickel-catalyzed dearylative cyclocondensation reaction of aldehydes, alkynes, and triphenylborane. The reaction proceeds under mild conditions, generating oxaboranes with high regioselectivity and moderate-to-high yields. This approach provides a direct and modular synthesis of oxaboranes, which are difficult to access using current methods, and has important implications in the synthesis of valuable building blocks for organic synthesis.
Article
Chemistry, Multidisciplinary
Oriol Planas, Vytautas Peciukenas, Markus Leutzsch, Nils Noethling, Dimitrios A. . Pantazis, Josep Cornella
Summary: This article presents a combined experimental and theoretical investigation of the C(sp(2))-F bond formation from neutral and cationic high-valent organobismuth(V) fluorides. The study reveals the impact of different ligands, sulfoximines, and reactive aryls on the kinetic and thermodynamic parameters of the reaction. The addition of external fluoride sources and the role of tetrafluoroborate anion are also explored. Both experimental and theoretical analyses demonstrate that C-F bond formation occurs through a low-energy five-membered transition-state pathway. The study provides a rational assessment of ligands and identifies a sulfone-based ligand family as an improved system for the fluorination of arylboronic acid derivatives.
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
(2022)
Article
Chemistry, Organic
Rayees Ahmad Naikoo, Rupesh Kumar, Parvesh Singh, Gaurav Bhargava
Summary: The manuscript discusses an efficient and atom economical synthesis method for pyrimido[4,5-b][1,4]benzodiazepin-4-ones through 7-endo-trig Pictet-Spengler type cyclisations. The synthetic approach involves the synthesis of different variants of 5-arylidene-amino-3H-pyrimidines and their cyclisations to afford biologically relevant functionalized benzodiazepine condensed pyrimidinones in good to excellent yields (82-94%).
SYNTHETIC COMMUNICATIONS
(2021)
Review
Chemistry, Medicinal
Kritika Laxmikeshav, Pooja Kumari, Nagula Shankaraiah
Summary: This review provides a comprehensive report on the design strategies of sulfur-bearing cytotoxic agents and their potential in anticancer therapy. The article discusses various sulfur-containing heterocyclic scaffolds and their cytotoxic effects through multiple mechanisms. The assessment of antiproliferative activities allows for a proficient evaluation of the structure-activity relationships of the synthesized molecules.
MEDICINAL RESEARCH REVIEWS
(2022)
Review
Biochemistry & Molecular Biology
Sarthak Jhingran, Kritika Laxmikeshav, Sayali Mone, Venkata K. Rao, Nagula Shankaraiah
Summary: Cancer, as a global health issue, poses a significant threat to human lives. DNA, being one of the major targets in cancer chemotherapy, can be effectively targeted by phenanthrene and its derivatives through intercalation and inhibition of DNA synthesis enzymes. However, the development of novel chemotherapeutic agents is crucial due to off-target effects and resistance. This review summarizes the recent progress in the development of phenanthrene-based derivatives, focusing on synthetic strategies, conjugation with other pharmacophores, and metal complexes. The cytotoxicity evaluation against various carcinoma cell lines and computational studies are also discussed, highlighting the potential of these derivatives as cytotoxic agents in medicinal chemistry.
CURRENT MEDICINAL CHEMISTRY
(2022)
Review
Chemistry, Organic
Jay Prakash Soni, Nayan Arvind Jadhav, Nagula Shankaraiah
Summary: This review focuses on the azido-reductive cyclization of organic azides and its significant insights. The review elaborates the extensive literature for synthesizing various heterocycles using chemoselective and straightforward protocols for azido-reduction with concomitant intramolecular cyclization. The azido-reductive cyclization strategy has been successfully applied in the synthesis of essential heterocycles and various iminosugars, drugs/APIs, and natural products embedding such heterocycles.
CURRENT ORGANIC CHEMISTRY
(2022)
Article
Chemistry, Multidisciplinary
Kritika Laxmikeshav, Akash P. Sakla, Stephy Elza John, Nagula Shankaraiah
Summary: A facile and proficient dithiocarbamation of imidazo[1,2-a]pyridines and other imidazoheterocycles is established using a copper(i) catalyst and molecular oxygen under microwave conditions, resulting in moderate to excellent yields. The synthesized derivatives have drug-like properties and good ADME/T profile, with compounds 3be and 3bb showing more potency towards MCF-7 human breast cancer cells compared to the standard drug 5-fluorouracil.
Article
Biochemistry & Molecular Biology
Jay Prakash Soni, G. Nikitha Reddy, Ziaur Rahman, Anamika Sharma, Akella Spandana, Regur Phanindranath, Manoj P. Dandekar, Narayana Nagesh, Nagula Shankaraiah
Summary: In this study, a series of new beta-carboline tethered indole-3-glyoxylamide derivatives were synthesized, which showed significant pharmacological properties and prominent cytotoxicity. The compounds exhibited remarkable cytotoxicity against human cancer cell lines, especially melanoma, and showed selective toxicity towards cancer cells compared to normal cells. The compounds induced apoptosis and showed potential as DNA binders and inhibitors of Topoisomerase II. Molecular modeling studies confirmed their excellent DNA intercalation potential. In addition, in silico analysis predicted the promising drug-like properties of the synthesized derivatives.
BIOORGANIC CHEMISTRY
(2023)
Article
Chemistry, Physical
Kritika Laxmikeshav, Pooja Sharma, Manisurya Palepu, Pravesh Sharma, Ashutosh Mahale, Joel George, Regur Phanindranath, Manoj P. Dandekar, Onkar Prakash Kulkarni, Narayana Nagesh, Nagula Shankaraiah
Summary: A new series of carboxamide-bearing benzimidazole derivatives have been investigated for their cytotoxicity on selected human tumor cells. Compounds 10g and 10m showed selective cytotoxicity towards SK-Mel-28 skin cancer cells and were safe for human non-cancerous lung epithelial cells.
JOURNAL OF MOLECULAR STRUCTURE
(2023)
Article
Chemistry, Multidisciplinary
Stephy Elza John, Anamika Sharma, Shivani Gulati, Darshana Bora, Nagula Shankaraiah
Summary: In modern medicinal chemistry, a molecular hybridization approach was used to design and synthesize a new class of cis-stilbene-based 1,2,4-triazole/1,3,4-oxadiazole conjugates. These conjugates exhibited promising cytotoxicity against selected human cancer cell lines, with cis-stilbene-based 1,2,4-triazole conjugate 5a being the most effective against the A549 cell line. Mechanistic analysis revealed that 5a induced apoptosis, DNA damage, nuclear morphological changes, and ROS generation, and exhibited G2/M phase arrest and tubulin polymerization inhibition. Additionally, 5a showed no toxicity towards normal cells and demonstrated significant anti-cancer activity.
NEW JOURNAL OF CHEMISTRY
(2023)
Article
Chemistry, Medicinal
Kritika Laxmikeshav, Mone Sayali, Geetanjali Devabattula, Durgesh G. G. Valapil, Ashutosh Mahale, Pravesh Sharma, Joel George, Regur Phanindranath, Chandraiah Godugu, Onkar P. P. Kulkarni, Narayana Nagesh, Nagula Shankaraiah
Summary: A simple click protocol was used to synthesize 1,2,3-triazole-linked benzimidazoles as potential anticancer agents, which showed significant cytotoxicity against SK-Mel-28 cancer cells and no cytotoxicity against normal BEAS-2B cells. Compound 12j inhibited cellular migration, colony formation, and induced apoptosis in SK-Mel-28 cells.
ARCHIV DER PHARMAZIE
(2023)
Article
Chemistry, Physical
Darshana Bora, Anamika Sharma, Stephy Elza John, Nagula Shankaraiah
Summary: A series of new combretastatin-oxindole derivatives were synthesized using (E)-bis(phenyl) acrylohydrazides and substituted isatins. The cytotoxic activity of these derivatives was evaluated against various cancer cell lines, and compound 9o showed potent anti-cancer activity against lung cancer cells. It induced changes in nuclear morphology and apoptosis, inhibited tubulin polymerization, and had a binding interaction with the 3E22 protein.
JOURNAL OF MOLECULAR STRUCTURE
(2023)
Article
Biochemistry & Molecular Biology
Akash P. Sakla, Biswajit Panda, Ashutosh Mahale, Pravesh Sharma, Kritika Laxmikeshav, Mursalim Ali Khan, Onkar Prakash Kulkarni, Chandraiah Godugu, Nagula Shankaraiah
Summary: In this study, regiospecific nucleophilic ring-opening of spiroaziridine oxindoles was performed to synthesize 3-substituted-thiooxindole derivatives as anticancer agents. Among the new compounds, 7d and 9c showed promising cytotoxic activity against HCT-116 cells with IC50 values of 6.73 ± 0.36 and 6.64 ± 0.95 μM, respectively. Further studies demonstrated significant alterations in nuclear and morphological characteristics, loss of mitochondrial membrane potential, and cell cycle arrest in G2-M phase for compound 9c. In addition, compound 9c exhibited tubulin polymerase inhibition with an IC50 value of 9.73 ± 0.18 μM, supported by docking interactions with tubulin.
BIOORGANIC & MEDICINAL CHEMISTRY
(2023)
Article
Chemistry, Organic
Sravani Sana, Srinivas Reddy Dannarm, Ramya Tokala, Sowmya Dastari, Manda Sathish, Rahul Kumar, Rajesh Sonti, Nagula Shankaraiah
Summary: A sustainable synthetic protocol for the construction of color-tunable fluorescent molecules has been achieved via ruthenium-catalyzed multiple C-H activation/annulation. The strategy provides easy access to a library of fused heterocyclic frameworks with significant yields. A systematic investigation of photophysical properties has also been conducted for the discovery of new fluorophores.
ORGANIC CHEMISTRY FRONTIERS
(2023)
Article
Chemistry, Organic
Sravani Sana, Sowmya Dastari, Dannarm Srinivas Reddy, Ramya Tokala, Manda Sathish, Rajesh Sonti, Nagula Shankaraiah
Summary: A sustainable protocol using a photoredox-mediated dual catalytic copper/ruthenium system has been developed for the construction of unsymmetrical diarylamines. This approach allows for the easy access to medicinally relevant amines by sequentially arylating ammonia with various (hetero)aryl bromides. The resulting mono-arylated amines can undergo a copper-mediated cross-coupling with aryl boronic acids, enabling the synthesis of the tyrosine kinase inhibitor Imatinib in an eco-friendly manner.
ORGANIC CHEMISTRY FRONTIERS
(2023)
Article
Chemistry, Organic
Yellaiah Tangella, Jay Prakash Soni, Nagula Shankaraiah, Diana Abril, Manda Sathish
Summary: A versatile and efficient one-pot protocol has been developed for the synthesis of amides from easily accessible carboxylic acids and amines by employing trimethylsilyl azide as a promoter at room temperature. This reaction proceeds via an in situ generated acyl azide intermediates followed by the nucleophilic substitution of amines. Notably, most of the desired amides were obtained by simple filtration in excellent yields. The significant advantages like metal-free mild reaction conditions, higher yields, easily removable volatile byproducts, operational simplicity, and broad substrate scope make the transformation a useful contribution for the synthesis of biologically important amides.
Article
Biochemistry & Molecular Biology
Jay Prakash Soni, Shrilekha Chilvery, Anamika Sharma, G. Nikitha Reddy, Chandraiah Godugu, Nagula Shankaraiah
Summary: A series of 2-((3-(indol-3-yl)-pyrazol-5-yl)imino)thiazolidin-4-ones were designed and synthesized as potential and effective chemotherapeutic agents. Compound 6c exhibited the highest cytotoxicity against melanoma cancer cells and showed selectivity towards cancer cells. It induced early-stage apoptosis, arrested cell-cycle in the G2/M phase, and inhibited tubulin polymerization. Molecular modeling studies confirmed its stable binding to tubulin and interactions with active pocket residues.
RSC MEDICINAL CHEMISTRY
(2023)
Article
Biochemistry & Molecular Biology
Darshana Bora, Khan Mehtab Samir, Anamika Sharma, Shrilekha Chilvery, Sapana Bansod, Stephy Elza John, Mursalim Ali Khan, Chandraiah Godugu, Nagula Shankaraiah
Summary: In this study, a new series of cis-stilbene-1,2,3-triazole congeners were synthesized and evaluated for their potential anticancer and tubulin polymerization inhibition activity. The most active compound, 9j, showed selective cytotoxicity against colorectal cancer cells and induced apoptotic cell death. It also inhibited tubulin polymerization and exhibited G2/M phase cell cycle arrest.
RSC MEDICINAL CHEMISTRY
(2023)