Article
Chemistry, Multidisciplinary
Zorana Ferjancic, Andrej Kukuruzar, Filip Bihelovic
Summary: An enantioselective total synthesis of the monoterpenoid indole alkaloid (+)-alstonlarsine A (1) has been achieved, which possesses a unique pentacyclic skeleton and rare biological activity. The key step involves an efficient domino sequence, consisting of enamine formation followed by an inverse-electron-demand intramolecular dearomative Diels-Alder cycloaddition for the construction of a 9-azatricyclo[4.3.1.0(3,8)]decane core. This strategy offers a new general entry into other tricyclic frameworks with fused indole ring and 6-, 7-, or 8-membered rings.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2022)
Article
Multidisciplinary Sciences
Andrew V. Kelleghan, Ana S. Bulger, Dominick C. Witkowski, Neil K. Garg
Summary: Since 1825, compounds with the molecular formula C6H6, especially benzene, have been extensively studied. However, the strained isomer 1,2,3-cyclohexatriene has been largely overlooked. This study demonstrates that 1,2,3-cyclohexatriene and its derivatives can undergo various reactions and be integrated into multistep syntheses, showing potential application in the synthesis of important compounds.
Article
Chemistry, Organic
Shuheng Xu, Linwei Zeng, Sunliang Cui
Summary: The Diels-Alder (DA) reaction and hetero-Diels-Alder (HDA) reaction are powerful methods for constructing carbocycles and heterocycles. This study presents an integrated building block that combines both DA and HDA reactions, utilizing triazenyl dienes to undergo the DA reaction and the newly released alkene moiety and triazene to engage in the HDA reaction.
Article
Chemistry, Organic
Gary L. Points, Christopher M. Beaudry
Summary: Substituted carbazoles are efficiently synthesized from 3-triflato-2-pyrones and alkynyl anilines, allowing for multiple substituents with complete control of regiochemistry, resulting in complex substitution patterns. This strategy can also be applied to prepare substituted bicarbazoles and related biaryls, and has been demonstrated in the synthesis of the carbazole natural product clausine C.
Article
Multidisciplinary Sciences
Xiang Gao, Tian-Jiao Han, Bei-Bei Li, Xiao-Xiao Hou, Yuan-Zhao Hua, Shi-Kun Jia, Xiao Xiao, Min-Can Wang, Donghui Wei, Guang-Jian Mei
Summary: The chiral phosphoric acid-catalyzed divergent intermolecular CADA reactions of common phenols with azoalkenes have been reported, which can efficiently synthesize tetrahydroindolone and cyclohexadienone products with an all-carbon quaternary stereogenic center in good yields.
NATURE COMMUNICATIONS
(2023)
Article
Chemistry, Multidisciplinary
David Fabian Leon Rayo, Young J. Hong, Dominic Campeau, Dean J. Tantillo, Fabien Gagosz
Summary: This article reports on the gold-catalyzed dehydro-Diels-Alder reactions of ynamide derivatives, which allow efficient access to various N-containing aromatic heterocycles. A dual gold catalysis mechanism was found, with the reaction proceeding in three stages: formation of a sigma,pi-digold complex, cyclization to produce a gem-diaurated aryl complex, and catalyst transfer to release the product and regenerate the sigma,pi-digold complex.
CHEMISTRY-A EUROPEAN JOURNAL
(2021)
Article
Chemistry, Multidisciplinary
Khaled Youssef, Magali Allain, Thomas Cauchy, Frederic Gohier
Summary: 2-Bromo, 3-bromothiophene, 2,5-dibromothiophene, 3,4-dibromothiophene, and perbrominated thiophene were oxidized under different conditions to form thiophene S,S-dioxide. Depending on the substitution, sulfone was obtained when the hindered thiophene was used. However, monosubstituted thiophenes could not be transformed into sulfone due to the reactivity of the sulfoxide intermediate, which led to dimerization. The structures were confirmed through the obtaining of crystals. The oxidation of 3,4-dibromothiophene could either result in the formation of cycloadduct or the isolation of sulfone, which could further evolve into benzothiophene sulfone.
NEW JOURNAL OF CHEMISTRY
(2023)
Article
Chemistry, Multidisciplinary
Wei Cao, Yingchao Dou, Cyrille Kouklovsky, Guillaume Vincent
Summary: The first total synthesis of the monoterpene indole alkaloids ophiorrhine A is reported via a late stage bioinspired intramolecular Diels-Alder cycloaddition. The synthesis includes the construction of the indolopyridone moiety, cyclodehydration, and the desired spontaneous intramolecular Diels-Alder cycloaddition.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2022)
Article
Chemistry, Multidisciplinary
Bo Qin, Zhepei Lu, Yanxing Jia
Summary: We have successfully achieved the divergent total synthesis of four kopsane alkaloids, which share a complex heptacyclic caged ring system. Key transformations in this synthesis include an asymmetric Diels-Alder reaction for constructing the central bicyclo[2.2.2]octane moiety and the quaternary stereocenter at C20, a SmI2-mediated cascade reduction/aldol reaction for constructing the five-membered ring and the quaternary stereocenter at C7, and a late-stage cascade reductive amination/cyclization for establishing the highly strained caged ring system.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2022)
Article
Chemistry, Multidisciplinary
Jiujian Ji, Jiajun Chen, Sixun Qin, Wanye Li, Jun Zhao, Guozhao Li, Hao Song, Xiao-Yu Liu, Yong Qin
Summary: This article reports the first total synthesis of vilmoraconitine using efficient ring-forming reactions. Key steps include an oxidative dearomatization-induced Diels-Alder cycloaddition, a hydrodealkenylative fragmentation/Mannich sequence, and an intramolecular Diels-Alder cycloaddition.
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
(2023)
Article
Chemistry, Multidisciplinary
Shaolei Ding, Yingbo Shi, Baochao Yang, Min Hou, Haibing He, Shuanhu Gao
Summary: We describe the asymmetric total synthesis of periglaucines A-C, N,O-dimethyloxostephine and oxostephabenine. Key strategies include a regio- and diastereoselective Hayashi-Miyaura reaction, an intramolecular photoenolization/Diels-Alder reaction, and a bio-inspired intramolecular Michael addition and transannular acetalization.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2023)
Article
Chemistry, Organic
Lukas Hoff, Simon D. Schnell, Andrea Tomio, Anthony Linden, Karl Gademann
Summary: A silver-mediated Pd-catalyzed cross-coupling method for 3-bromo-1,2,4,5-tetrazine with boronic acids was presented in this study. It was found that electronic modification of the dppf ligand played a crucial role in achieving good turnover. Using this fast method, a variety of alkyl-, heteroatom-, and halide-substituted aryl- and heteroaryl-tetrazines were successfully prepared, with yields up to 87%.
Article
Chemistry, Organic
Jonathan P. Knowles, Hannah G. Steeds, Maria Schwarz, Francesca Latter, Kevin Booker-Milburn
Summary: This method transforms simple starting materials into complex tetracyclic products with potential medicinal chemistry applications through a sophisticated chemical catalysis process.
Article
Chemistry, Physical
Jinbo Zhang, Manli Ma, Rong Zhou, Hongqiang Chu, Xue Wang, Shaojie Wang, Huhu Tian, Zhipeng Yan, Mingtao Li, Zhongyan Wu, Bin Li, Jiafeng Yan, Lan Anh Thi Nguyen, Rongxing Cao, Guoqing Wu, Xianghua Zeng, Hao-Li Zhang, Jaeyong Kim, Lin Wang, Yongjun Tian
Summary: In this study, it is demonstrated using multiple characterization techniques that the bowl-shaped clusters C18Te3Br4(Bu-O)(6) may undergo a Dehydro-Diels-Alder (DDA) reaction at high pressure, resulting in crystalline carbon materials with different transport properties.
Article
Chemistry, Multidisciplinary
Marlene Fadel, Erick M. Carreira
Summary: The first total synthesis of (+)-pedrolide, a tigliane-derived diterpenoid featuring an unprecedented 5-5-6-6-3 carbon skeleton, was achieved. A key step in the synthesis involved the construction of the bicyclo[2.2.1]heptane core via an intramolecular cyclopentadiene-Diels-Alder cycloaddition. A norbornadiene was used as a surrogate for cyclopentadiene, and the unmasking of the cyclopentadiene was achieved through a complex Diels-Alder reaction cascade. This synthesis also provided a novel approach to a densely functionalized carane in an efficient and enantioselective manner.
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
(2023)
Article
Chemistry, Organic
Nagnath Yadav More, Masilamani Jeganmohan
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY
(2017)
Article
Chemistry, Organic
Nagnath Yadav More, Kishor Padala, Masilamani Jeganmohan
JOURNAL OF ORGANIC CHEMISTRY
(2017)
Article
Chemistry, Multidisciplinary
Bibhisan Roy, Mallu Chenna Reddy, Partha Hazra
Article
Nanoscience & Nanotechnology
Prachi Kour, Mallu Chenna Reddy, Rounak Naphade, Satishchandra Ogale
Article
Chemistry, Physical
Bibhisan Roy, Mallu Chenna Reddy, Soumendra Nath Panja, Partha Hazra
JOURNAL OF PHYSICAL CHEMISTRY C
(2019)
Article
Chemistry, Physical
Bibhisan Roy, Mallu Chenna Reddy, Gregor P. Jose, Felix C. Niemeyer, Jens Voskuhl, Partha Hazra
Summary: This study presents a pair of luminogens with white light emission and temperature-induced mechanochromic features, capable of specifically illuminating mitochondria with a high Pearson coefficient value. The research opens up new possibilities for designing next generation organic luminogens with potential applications in optical, materials, and biological fields.
JOURNAL OF PHYSICAL CHEMISTRY LETTERS
(2021)
Article
Chemistry, Multidisciplinary
Prachi Kour, Mallu Chenna Reddy, Shiv Pal, Siraj Sidhik, Tisita Das, Padmini Pandey, Shatabdi Porel Mukherjee, Sudip Chakraborty, Aditya D. Mohite, Satishchandra Ogale
Summary: A new low-dimensional hybrid perovskitoid with unique structure and excellent optical properties was synthesized, showing potential applications in photodetectors and selective detection of metal ions.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2021)
Article
Chemistry, Medicinal
Jian Huang, Qiong Shi, Namrta Choudhry, Hongmei Li, Chenglu Yang, Julia Kalashova, Ziqi Yan, Jinhua Li, Mallu Chenna Reddy, Sridhar Goud Gopala, Shenqiu Zhang, Jing Zhang, Naganna Nimishetti, Dun Yang
Summary: Mechanism-informed phenotypic screening was used to identify and optimize compounds that mimic the genetic depletion of AURKB kinase. These compounds exhibited potent cytotoxic activities in various cancer cell lines and showed excellent drug-like properties. The findings suggest that seven-membered lactam-based analogs could be valuable for the development of new antimitotic agents for cancer treatment.
ACS MEDICINAL CHEMISTRY LETTERS
(2022)
Article
Biochemistry & Molecular Biology
Gang Lv, Qiong Shi, Ting Zhang, Jinhua Li, Yan Long, Wenhui Zhang, Namrta Choudhry, Kevin Yang, Hongmei Li, Julia Kalashova, Chenglu Yang, Xiaohu Zhou, Mallu Chenna Reddy, Kishore Kumar Anantoju, Shenqiu Zhang, Jing Zhang, Thaddeus D. Allen, Hong Liu, Naganna Nimishetti, Dun Yang
Summary: In this study, a mechanism-informed phenotypic screening (MIPS) assay combined with a structural simplification strategy was used to discover compounds that disrupt the localization of AURKB. A lead compound, N-(3-methoxy-5-(6-methoxyquinolin-4-yl)oxy)phenyl)acetamide, was identified that effectively inhibits AURKB's mitotic localization and induces severe growth inhibition in human cancer cell lines. This lead compound also showed AURKB-inhibitory phenotypes in a mouse xenograft model, making it a potential first-in-class oncology therapeutic.
BIOORGANIC & MEDICINAL CHEMISTRY
(2023)
Article
Chemistry, Medicinal
Gang Lv, Qiong Shi, Ting Zhang, Jinhua Li, Julia Kalashova, Yan Long, Yin Sun, Chao Li, Namrta Choudhry, Hongmei Li, Chenglu Yang, Xiaohu Zhou, Mallu Chenna Reddy, Kishore Kumar Anantoju, Rajesh Jupelli, Shenqiu Zhang, Jing Zhang, Thaddeus Allen, Hong Liu, Naganna Nimishetti, Dun Yang
Summary: Activity-based drug screens have led to the development of inhibitors for aurora kinases (AURKs), but disrupting the localization of AURKB is an alternative approach worth exploring. The pan-AURK inhibitor AMG900 was shown to disrupt the localization of AURKB rather than inhibiting its phosphorylation of H3 at Ser10. Further studies revealed that certain derivatives of 2-phenoxy-3,4'-bipyridine have the potential to be developed as effective therapeutics for malignancy by delocalizing AURKB.
EUROPEAN JOURNAL OF MEDICINAL CHEMISTRY
(2023)
Article
Chemistry, Multidisciplinary
Swati Parmar, Shiv Pal, Abhijit Biswas, Suresh Gosavi, Sudip Chakraborty, Mallu Chenna Reddy, Satishchandra Ogale
CHEMICAL COMMUNICATIONS
(2019)
Article
Chemistry, Multidisciplinary
Nagnath Yadav More, Masilamani Jeganmohan
CHEMICAL COMMUNICATIONS
(2017)
Article
Chemistry, Multidisciplinary
Rajendran Manikandan, Masilamani Jeganmohan
CHEMICAL COMMUNICATIONS
(2017)
Article
Chemistry, Multidisciplinary
Alexander M. Prophet, Kritanjan Polley, Gary J. Van Berkel, David T. Limmer, Kevin R. Wilson
Summary: The oxidation kinetics of iodide by ozone at the air-water interface is studied in single microdroplets. Molecular simulations and kinetic modeling are used to understand the underlying multiphase mechanism.
Article
Chemistry, Multidisciplinary
Rong Zhang, Jiajing Lan, Fei Wang, Shumei Chen, Jian Zhang
Summary: By utilizing 1,1'-ferrocene dicarboxylic acid as a chelating and surface protection ligand, we have synthesized multi-nuclear indium oxide clusters with varying nuclear sizes, including heptanuclear and thirteen-nuclear clusters. These clusters possess labile coordination sites, allowing for structural modification and self-assembly, resulting in the formation of various cluster structures.
Article
Chemistry, Multidisciplinary
Hui Wang, Hui Liu, Mingsen Wang, Jiaheng Hou, Yongjun Li, Yuancheng Wang, Yingjie Zhao
Summary: Two supramolecular complexes were prepared using CBs and M1, and their single-crystal structures were analyzed by SCXRD. The unexpected 1:2 self-assembly structure between M1 and CB[8] was discovered for the first time. These complexes exhibit unique photophysical properties and provide valuable information about the structure and photophysical properties of supramolecular complexes.
Article
Chemistry, Multidisciplinary
Chang-Hee Lee, Sookil Park, Sanggil Kim, Ji Young Hyun, Hyun Soo Lee, Injae Shin
Summary: The epidermal growth factor receptor (EGFR) is a cell-surface glycoprotein involved in cell proliferation and tumor development. This study used a fluorescently labeled EGFR to investigate its time-dependent endocytosis in live cells and found that appended glycans affect EGFR internalization. Additionally, the study detected sialic acid residues attached to EGFR on the live cell surface using FRET-based imaging. This research provides valuable insights into the cellular functions of EGFR.
Article
Chemistry, Multidisciplinary
Subhankar Sahu, Lokesh Kumar, Sumita Das, Dipti Gupta, Ruchi Anand
Summary: This study proposes a strategy that combines organic electronics with biosensor scaffolds to create a compact device for monitoring environmental aromatic pollution. By coupling biosensing protein MopR with an organic electrochemical transistor (OECT), a sensor module capable of efficient detection of phenol was designed. Exclusive phenol detection with minimal loss of sensitivity could be achieved in complex pollutant mixtures and real environmental samples.
Review
Chemistry, Multidisciplinary
Changseok Lee, Hyung-Joon Kang, Sungwoo Hong
Summary: The formation of C-N bonds through hydroamination reactions catalyzed by nickel hydrides has been a topic of recent interest. This approach offers a way to efficiently transform a variety of alkene and alkyne substrates into compounds enriched with C-N bonds. The review provides a concise overview of the underlying reaction mechanisms and aims to stimulate further progress in NiH-catalytic techniques and catalyst design.
Article
Chemistry, Multidisciplinary
Yueci Wu, Lu-Lu Sun, Hai-Hao Han, Xiao-Peng He, Weiguo Cao, Tony D. James
Summary: Drug-induced liver injury (DILI) is a common cause of acute liver failure in the USA and Europe, but most cases can be recovered or prevented by discontinuing the offending drug. Recent research has found that peroxynitrite (ONOO-) can be used as a potential indicator for early diagnosis of DILI, and there is an urgent need to establish a method to detect and track peroxynitrite in DILI cases. In this study, a FRET-based nano fluorescent probe CD-N-I was developed, which showed high selectivity and sensitivity in detecting peroxynitrite. The probe successfully detected exogenous peroxynitrite in live cells and endogenous peroxynitrite in APAP-induced liver injury of HepG2 cells.
Article
Chemistry, Multidisciplinary
Dmitry L. Lipilin, Mikhail O. Zubkov, Mikhail D. Kosobokov, Alexander D. Dilman
Summary: This article describes a direct photocatalytic method for the thiolation of unprotected acids, which was previously challenging. By using a thionocarbonate reagent with an N-O bond, the efficient conversion of carboxylic acids to thiols is achieved.
Article
Chemistry, Multidisciplinary
Jason Malenfant, Lucille Kuster, Yohann Gagne, Kouassi Signo, Maxime Denis, Sylvain Canesi, Mathieu Frenette
Summary: Raman microscopy can reveal compound-specific vibrational fingerprints without sample preparation. The combination of efficient theoretical calculations and a user-friendly software can accurately predict peak positions and provide match scores to assist with structure determination.
Article
Chemistry, Multidisciplinary
Jayoh A. Hernandez, Paul S. Micus, Sean Alec Lois Sunga, Luca Mazzei, Stefano Ciurli, Gabriele Meloni
Summary: Essential trace metals play crucial roles in the survival and virulence of bacterial pathogens. Helicobacter pylori requires nickel for colonization and persistence in the stomach, and NixA is an essential nickel transporter in this process. This study characterizes the selectivity and electrogenic nature of NixA-mediated nickel transport.
Article
Chemistry, Multidisciplinary
Tarali Devi, Kuheli Dutta, Jennifer Deutscher, Stefan Mebs, Uwe Kuhlmann, Michael Haumann, Beatrice Cula, Holger Dau, Peter Hildebrandt, Kallol Ray
Summary: This study emphasizes the importance of subtle electronic changes and secondary interactions in the stability of biologically relevant metal-dioxygen intermediates. It also shows that the role of the chloride ligand in stabilizing the Fe-III-(OOBu)-Bu-t moiety can extend to other anions, including the thiolate ligand.
Article
Chemistry, Multidisciplinary
Jacqueline R. Santhouse, Jeremy M. G. Leung, Lillian T. Chong, W. Seth Horne
Summary: By studying the folding kinetics and mechanism of the BdpA sequence, researchers found that altering the backbone connectivity can affect protein folding. This suggests that protein mimetic chains have a significant degree of plasticity in transitioning between unfolded and folded states.
Article
Chemistry, Multidisciplinary
Divanshu Gupta, Ralf Einholz, Holger F. Bettinger
Summary: This study presents the first direct spectroscopic evidence of a cyclic seven-membered iminoborane. Compared to linear amino-iminoboranes, this cyclic iminoborane exhibits weakened bond strength and lower Lewis acidity value. The study suggests that the reduced ring strain of cyclic iminoborane prevents nitrogen fixation but allows facile (2 + 2) cycloaddition reaction with C2H4.
Article
Chemistry, Multidisciplinary
Renny Mathew, Aniruddha Mazumder, Praveen Kumar, Julie Matula, Sharmarke Mohamed, Petr Brazda, Mahesh Hariharan, Brijith Thomas
Summary: This study reveals the packing arrangement of partially disordered nitro-perylenediimide (NO2-PDI) using a synergistic approach that combines 3D ED, ssNMR, and DFT techniques. By overcoming these challenges, this methodology opens up new avenues for material characterization, driving exciting advancements in the field.
