- Click Chemistry Approach for Bis-Chromenyl Triazole Hybrids and Their Antitubercular Activity
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1,4-Disubstituted bis-chromenyl triazole hybrids 5a-m have been synthesized in a three-step reaction sequence from 4-(bromomethyl)-2H-chromen-2-ones 3a-m. The intermediate azides 4a-m underwent a regioselective 1,3-dipolar cycloaddition with a 2H-chromen-2-one linked acetylenic dipolarophile in the presence of Cu (II)/ascorbate/water/n-butanol reaction medium. Three compounds 5h-j exhibited 6.25μg/mL MIC against M. tuberculosis. Among the compounds screened for antifungal activity, lowest MIC of 6.25μg/mL was observed for 5c against A. niger that also exhibited DNA cleavage observed by agarose gel electrophoresis. All the compounds were moderately active against both Gram-positive and Gram-negative bacterial strains. The cytotoxic effect of potent compounds on normal cells (V79 and HBL100) was assessed by MTT assay.
- Naik, Reshma J.,Kulkarni, Manohar V.,Sreedhara Ranganath Pai,Nayak, Pawan G.
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- A targeted, image-guided and dually locked photoresponsive drug delivery system
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We have developed a new targeted image-guided photoresponsive drug delivery system (DDS) based on a dual locking strategy. Excitation of the DDS by fluorescent light results in the first unlocking and activation of the drug, and allows real-time monitorin
- Karthik,Prashanth Kumar,Gangopadhyay, Moumita,Mandal, Mahitosh,Singh, N. D. Pradeep
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- Synthesis of coumarin-theophylline hybrids as a new class of anti-tubercular and anti-microbial agents
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A series of novel coumarin-theophylline hybrids were synthesized and examined for their anti-tubercular activity in vitro against Mycobacterium tuberculosis H37Rv, anti-microbial activity in vitro against gram-positive bacteria (Staphylococcus aureus) and gram-negative bacterias (Escherichia coli, Salmonella typhi) as well as fungi (Candida albicans). The compound (3a) has shown excellent anti-tubercular activity with MIC of 0.12 μg/mL. Electron donating compounds (3a, 3f) have displayed significant anti-microbial activity. The compounds have also been precisely elucidated using single crystal X-ray diffraction techniques. Molecular docking study has been performed against 4DQU enzyme of Mycobacterium tuberculosis showed good binding interactions and is in agreement with the in vitro results.
- Mangasuli, Sumitra N.,Hosamani, Kallappa M.,Devarajegowda, Hirihalli C.,Kurjogi, Mahantesh M.,Joshi, Shrinivas D.
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- Preparation and molecular recognition of SERS probe based on gold nanoparticles constructed from PEG-oligoamine copolymer possessing a coumarin group between PEG and oligoamine
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Novel gold nanoparticles (GNPs) as a SERS probe were prepared using two types of functional PEG/oligoamine polymers possessing biotin as biotag molecules at the PEG end or a coumarin moiety as a Raman probe molecule between the PEG and oligoamine segments. Eventually, the GNPs showed excellent dispersion stability under physiological conditions, as well as remarkable SERS signal resulting from molecular recognition between streptavidin and the biotin tag, even in the presence of bovine serum albumin (BSA).
- Furusho, Hitoshi,Oishi, Motoi,Kishi, Tetsuo,Yasumori, Atsuo,Nagasaki, Yukio
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- Synthesis of a PEGylated polymeric pH sensor and its pH sensitivity by fluorescence resonance energy transfer
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A new pH-sensitive polymeric sensor with dispersion stability and biocompatibility is synthesized, and its pH sensitivity is examined on the basis of the fluorescence resonance energy transfer (FRET) efficiency. The polymeric pH sensor has a FRET donor an
- Hong, Sung Woo,Ahn, Cheol-Hee,Huh, June,Jo, Won Ho
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- Chemistry, chemical biology and photophysics of certain new chromene-triazole-coumarin triads as fluorescent inhibitors of CDK2 and CDK4 induced cancers
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A new series of chromene-triazole-coumarin triads (T1 to T6) have been synthesized through the employment of a solvent-free mechanochemical multicomponent reaction, followed by a copper catalyzed (3+2) azide-alkyne cycloaddition (click chemistry). The mol
- Shankar, E. P. Shyam,Bahulayan, Damodaran
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- Coumarin polycaprolactone polymeric nanoparticles: light and tumor microenvironment activated cocktail drug delivery
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Highly sensitive hypoxia (H2O2)-activated photoresponsive polymeric nanoparticles for cocktail delivery of anticancer drugs doxorubicin (Dox) and chlorambucil (Cbl) were developed. The photoresponsive polymer conjugate was constructe
- Karthik,Jana, Avijit,Selvakumar,Venkatesh, Yarra,Paul, Amrita,Shah, Sk. Sheriff,Singh, N. D. Pradeep
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- Synthesis of furocoumarin–stilbene hybrids as potential multifunctional drugs against multiple biochemical targets associated with Alzheimer's disease
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A series of furocoumarin-stilbene hybrids has been synthesized and evaluated in vitro for inhibitory effect against acetylcholinesterase (AChE), butyrylcholinestarase (BChE), β-secretase, cyclooxygenase-2 (COX-2), and lipoxygenase-5 (LOX-5) activities including free radical-scavenging properties. Among these hybrids, 8-(3,5-dimethoxyphenyl)-4-(3,5-dimethoxystyryl)furochromen-2-one 4h exhibited significant anticholinesterase activity and inhibitory effect against β-secretase, COX-2 and LOX-5 activities. 2,2-Diphenyl-1-picrylhydrazyl (DPPH) radical scavenging activity and an in vitro cell-based antioxidant activity assay involving lipopolysaccharide induced reactive oxygen species production revealed that 4h has capability of scavenging free radicals. Molecular docking into AChE, BChE, β-secretase, COX-2 and LOX-5 active sites has also been performed.
- Agbo, Emmanuel N.,Choong, Yee Siew,Gildenhuys, Samantha,More, Garland K.,Mphahlele, Malose J.
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- Synthesis and biological evaluation of novel coumarin derivatives as antioxidant agents
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Coumarins have been isolated from plants and reported for antioxidant properties. In the present study, we report synthesis of new coumarin derivatives as prospective therapeutic agents and investigate their antioxidant properties.
- Randive,Jaishree,Patil, K. Santosh,Patil, Kumar
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- A lysosome-targetable fluorescent probe for simultaneous detection and discrimination of Cys/Hcy and GSH by dual channels
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Small molecule biothiols, such as cysteine (Cys), homocysteine (Hcy) and glutathione (GSH), are important biomarkers and play vital roles in many physiological processes. Due to their similarity in structure and function, it is still a challenge to develop probes that can simultaneously distinguish Cys, Hcy and GSH from each other. Lysosome is a major subcellular organelle in living cells that contains approximately 50 different degradative enzymes, and biothiols play an important role in lysosome. Herein, we developed a lysosome-targetable probe Lyso-O-NBD for simultaneous detection and discrimination of Cys/Hcy and GSH by dual channels. Under double-wavelength excitation of 400 nm and 470 nm, the probe Lyso-O-NBD showed high selectivity and sensitivity towards Cys/Hcy and GSH over other amino acids and ions. Furthermore, the probe Lyso-O-NBD could be used for simultaneous detection and discrimination of Cys/Hcy and GSH in lysosome of living cells with low cytotoxicity.
- Song, Xufen,Tu, Yayi,Wang, Renjie,Pu, Shouzhi
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- Synthesis, characterization, biological evaluation and docking of coumarin coupled thiazolidinedione derivatives and its bioisosteres as PPARγ agonists
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Thiazolidinedione (TZD) derivatives are the novel class of oral antidiabetic drugs which are selective agonist for the nuclear PPAR γ that enhances the transcription of several insulin responsive genes but TZDs are known to cause weight gain, hepatotoxicity and fluid retention. So a new series of coumarin coupled thiazolidinedione derivatives and its bioisosters (oxazolidinedione and imidazolidinedione) were synthesized by Knoevenagel condensation of 4-((7-hydroxy-2-oxo-2H-chromen-4-yl) methoxy) benzaldehyde with 2,4 thiazolidinedione and its bioisosteres. The structures of these compounds were established by means of FT IR, 1H-NMR, elemental analysis and mass spectroscopy. All the compounds were screened for antidiabetic activity in streptozotocin induced diabetic wistar male rats. Most of the compounds revealed significant antidiabetic activity when compared with the standard drug rosiglitazone. Compounds 5 & 6 containing oxazolidinedione ring system were found to be more active than compounds having thiazolidinedione and imidazolidinedione nucleus. Molecular docking was performed on 2 PRG protein by using the software Glide (Schroedinger, LLC, USA). The QikProp program was used to obtain the pharmacokinetic properties of analogues.
- Shukla, Shubhanjali,Das, Nirupam,Shrivastava, Sushant Kumar,Srivastava, Radhey Shyam,Kumar, Pankaj,Moorthy, N. S. Hari Narayana,Trivedi, Piyush
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- Microwave facilitated one-pot three component synthesis of coumarin-benzoxazole clubbed 1,2,3-triazoles: Antimicrobial evaluation, molecular docking and in silico ADME studies
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4-((4-((Benzo[d]oxazol-2-ylthio)methyl)-1H-1,2,3-triazol-1-yl)methyl)-2H-chromen-2-ones 7k–z were synthesized by conventional as well as microwave irradiation method in order to obtain antimicrobial agents. The present green synthetic protocol explores facile work up procedure with excellent yields (82–92%) and purity. Docking studies exhibited strong binding interactions with enzyme N-myristoyl transferase (PDB ID: 4CAW) with excellent C-score values. Compounds 7k–z were screened for their in vitro antimicrobial activities. The compounds 7w and 7 y exhibited excellent antimicrobial results for all the tested microorganisms at MICs ranging from 3.12 to 6.25 μg/ml in comparison with the marketed drugs.
- Nesaragi, Aravind R.,Kamble, Ravindra R.,Bayannavar, Praveen K.,Metre, Tukaram V.,Kariduraganavar, Mahadevappa Y.,Margankop, Sheetal B.,Joshi, Shrinivas D.,Kumbar, Vijay M.
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p. 3460 - 3472
(2021/10/02)
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- Synthesis and preliminary evaluation of benzofuran-oxadiazole conjugates as potential antitubercular agents
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In the present study, a series of benzofuran-oxadiazole conjugates 7(a-o) was designed, synthesized and characterized through IR,1H NMR,13C NMR and mass spectral data. All the compounds were screened for preliminary antitubercular activity against Mycobacterium phlei and Mycobacterium tuberculosis H37RV. Among all the target compounds, the compound possessing chlorine (7k, MIC 1.56 μg/mL) and bromine (7m, MIC 1.56 μg/mL) on 6th position of benzofuran showed highest activity against Mycobacterium phlei. Whereas, bromine on either 5th position (7l, MIC 3.125 μg/mL) or 6th position (7m MIC 3.125 μg/mL) on benzofuran exhibited highest activity for Mycobacterium tuberculosis (H37 RV).
- Negalurmath, Veerabhadrayya S.,Kotresh, Obelannavar,Basanagouda, Mahantesha
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p. 965 - 970
(2019/03/07)
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- Synthesis of coumarin-benzotriazole hybrids and evaluation of their anti-tubercular activity
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Background: Tuberculosis is one of the top ranked airborne infectious diseases caused by the bacillus Mycobacterium tuberculosis with high mortality rate from a single infectious agent. In the present article, we aimed to synthesize oxadiazole-coumarin-triazole based small molecules and evaluate for their possible anti-mycobacterial activity. Method: Herein, we describe the facile synthesis of 5-((1H-benzo[d][1, 2, 3]triazol-1-yl)methyl)-1, 3, 4- oxadiazole-2-thiol-tethered substituted 4-(bromomethyl)-7-methyl-2H-chromen-2-one derivatives and evaluated for their anti-mycobacterial activity against H37Rv strain of M. tuberculosis. We also evaluated the cytotoxic effect of new compounds on normal cells. Results: Among the 14 novel oxadiazole-coumarin-triazole derivatives, 4-((5-((1H-benzo[d][1, 2, 3]triazol-1- yl)methyl)-1, 3, 4-oxadiazol-2-ylthio)methyl)-6-methoxy-2H-chromen-2-one (5f) displayed good antimycobacterial activity towards M. tuberculosis with an MIC value of 15.5 μM. Pyrazinamide was used as reference drug. Our investigation also revealed that, 5f is not cytotoxic to normal cells. Conclusion: In summary, the findings suggested that novel 1, 3, 4-oxadiazole coumarin-triazole hybrids are promising antimycobacterial agents against M. tuberculosis.
- Ambekar, Sachin P.,Mohan, Chakrabhavi Dhananjaya,Shirahatti, Arunkumar,Kumar, Mahesh K.,Rangappa, Shobith,Mohan, Surender,Basappa,Kotresh, Obelannavar,Rangappa, Kanchugarakoppal S.
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- Click chemistry approach for the regioselective synthesis of iso-indoline-1,3-dione-linked 1,4 and 1,5 coumarinyl 1,2,3-triazoles and their photophysical properties
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Copper-catalyzed reaction of N-propargyl isoindoline-1,3-dione and 4-azidomethyl coumarins / 4-azidomethyl-1-aza coumarins under click chemistry conditions afforded 1,4-disubstituted 1,2,3-triazoles, whereas ruthenium catalysis yielded isomeric 1,5-disubstituted 1,2,3-triazoles. The two regioisomers have been distinguished by NOE studies. UV absorption for a given pair of isomers exhibited similar trend, whereas fluorescence measurements showed considerable differences. Photo physical studies on the interaction of azides with copper and ruthenium have also been performed.
- Anand, Ashish,Kulkarni, Manohar V.
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supporting information
p. 722 - 733
(2017/03/27)
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- Photosensitive targeted antineoplastic prodrug for responding to glutathione to kill tumor cells and preparation method and application thereof
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The invention discloses design and application of a drug and fluorescence dual-release system based on glutathione and photo-stimulation and designs and synthesizes a glutathione and photo-stimulation-based drug and fluorescence dual-release system. The glutathione and photo-stimulation-based drug and fluorescence dual-release system takes target molecules released by the drug of glutathione and 2, 4-dinitrobenzene sulfonyl chloride as response groups. Detection of the fluorescence performance of a prodrug (CM-2) shows that the prodrug (CM-2) can well respond to the glutathione to release fluorescence; meanwhile, compared with other photosensitive drugs, the prodrug is higher in stability and targeting property; measurement of antineoplastic activity research through an MTT (3-(4, 5-Dimethylthiazol-2-yl)-2, 5-diphenyltetrazolium bromide) method shows that the antineoplastic activity of the compound (CM-2) is higher than that of chlorambucil and accordingly shows that the targeting property of the compound (CM-2) is higher than that of the chlorambucil; the drug ingestion situation of cells is researched according to the fluorescence characteristics of coumarins, and experimental results show that the prodrug can be ingested by cells. The glutathione and photo-stimulation-based drug and fluorescence dual-release system provides an effective research tool for drug release of cell research.
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Paragraph 0019
(2017/10/23)
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- Redox-responsive xanthene-coumarin-chlorambucil-based FRET-guided theranostics for "activatable" combination therapy with real-time monitoring
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A FRET donor-acceptor xanthene-coumarin conjugate has been designed for redox-regulated synergic treatment of photodynamic therapy and chemotherapy with real-time monitoring. The "locked" FRET pair was selectively "unlocked" by biological reducing thiols via rupture of a sacrificial disulfide linker. A distinct change in fluorescence color and selective cancer cell toxicity were observed in vitro.
- Gangopadhyay, Moumita,Mengji, Rakesh,Paul, Amrita,Venkatesh, Yarra,Vangala, Venugopal,Jana, Avijit,Singh, N. D. Pradeep
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supporting information
p. 9109 - 9112
(2017/08/17)
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- Click-on fluorescent triazolyl coumarin peptidomimetics as inhibitors of human breast cancer cell line MCF-7
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The development of a series of multipurpose triazolyl coumarin peptidomimetics that can also work as click-on fluorescent inhibitors of human breast cancer cell line MCF-7 is described. The quantum mechanical calculations indicate that the click-on fluore
- Thasnim,Bahulayan
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supporting information
p. 13483 - 13489
(2017/11/27)
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- Efficient and Convenient Method for Synthesis of Benzofuran-3-acetic Acids and Naphthafuran-acetic Acids
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Herein, we report an efficient and convenient method for synthesis of benzofuran-3-acetic acids and naphthafuran-acetic acids 5a-p by the reaction of substituted-4-bromomethylcoumarins with aqueous sodium hydroxide at refluxing temperature. The obtained products are characterized by infrared, 1H NMR, 13C NMR, and mass spectral data. Structures 5a and 5e are confirmed by their single x-ray diffraction studies. The advantages of this method are good yields, easy workup, and no chromatographic purifications.
- Basanagouda, Mahantesha,Narayanachar,Majati, Iranna B.,Mulimani, Shiddappa S.,Sunnal, Satish B.,Nadiger, Rohit V.,Ghanti, Ashok S.,Gudageri, Siddeshwar F.,Naik, Ravi,Nayak, Akshata
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p. 2195 - 2202
(2015/09/22)
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- Fluorescence ratiometric zinc sensors based on controlled energy transfer
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The high-fidelity detection of labile zinc is of central importance for understanding the molecular mechanisms that link zinc homeostasis and human pathophysiology. Fluorescence ratiometric sensors are most suitable for the detection and trafficking of intracellular zinc ions. Here, we report the development of fluorescence ratiometric zinc sensors (HN1 and HN2) based on two-fluorophore platforms. The sensor constructs include blue fluorescent umbelliferone and an energy-accepting chromophore that absorbs the blue fluorescence. Zinc binding was found to promote fluorescence turn-on of the umbelliferone emission by suppression of intramolecular photoinduced electron transfer, thereby facilitating resonance energy transfer to the energy acceptors. The net observables were the fluorescence ratiometric changes, the extent of which depended strongly on the chemical structures of the acceptors. Photophysical investigations, including steady-state and transient photoluminescence spectroscopy, suggested a mechanism for the fluorescent zinc response that involved a combination of the intramolecular electron transfer and the interchromophoric energy transfer. The zinc probes displayed sensing capability that is suitable for the detection of biological zinc ions, with good selectivity, pH tolerance, and appropriate Kd values. Finally, zinc detection was demonstrated by fluorescence ratiometric visualization of exogenously supplied zinc ions in live HeLa cells. The probes enabled the reliable monitoring of zinc equilibration across the cell membrane. The Royal Society of Chemistry 2012.
- Woo, Hana,You, Youngmin,Kim, Taehee,Jhon, Gil-Ja,Nam, Wonwoo
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p. 17100 - 17112
(2012/11/07)
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- Synthesis, characterization, biological evaluation and docking of coumarin coupled thiazolidinedione derivatives and its bioisosteres as PPARγ agonists
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Thiazolidinedione (TZD) derivatives are the novel class of oral antidiabetic drugs which are selective agonist for the nuclear PPAR γ that enhances the transcription of several insulin responsive genes but TZDs are known to cause weight gain, hepatotoxicity and fluid retention. So a new series of coumarin coupled thiazolidinedione derivatives and its bioisosters (oxazolidinedione and imidazolidinedione) were synthesized by Knoevenagel condensation of 4-((7-hydroxy-2-oxo-2H-chromen-4-yl) methoxy) benzaldehyde with 2,4 thiazolidinedione and its bioisosteres. The structures of these compounds were established by means of FT IR, 1H-NMR, elemental analysis and mass spectroscopy. All the compounds were screened for antidiabetic activity in streptozotocin induced diabetic wistar male rats. Most of the compounds revealed significant antidiabetic activity when compared with the standard drug rosiglitazone. Compounds 5 & 6 containing oxazolidinedione ring system were found to be more active than compounds having thiazolidinedione and imidazolidinedione nucleus. Molecular docking was performed on 2 PRG protein by using the software Glide (Schroedinger, LLC, USA). The QikProp program was used to obtain the pharmacokinetic properties of analogues.
- Shukla, Shubhanjali,Kumar, Pankaj,Das, Nirupam,Moorthy, N.S. Hari Narayana,Shrivastava, Sushant Kumar,Trivedi, Piyush,Srivastava, Radhey Shyam
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p. 834 - 845
(2013/01/14)
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- Design, synthesis and characterization of some novel 3-coumarinyl- 5-aryliden-1,3-thiazolidine-2,4-diones and their antioxidant activity
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In our effort to obtain biologically active compounds, new 3,5-disubstituted 1,3-thiazolidine-2,4- diones (5a - r) were synthesized. A series of 5-arylmethylidene-1,3-thiazolidine-2,4-diones (3a - r) were prepared by Knoevenagel reaction from 1,3-thiazolidine-2,4-dione (2) and appropriate aromatic aldehydes. Condensation of 3a - r with 7-hydroxy-4-bromomethyl-2-oxo- 2H-chromene (1) afforded novel 3-(7-hydroxy-2-oxo-2H-chromen-4-ylmethyl)-5- arylidene-1,3-thiazolidine-2,4-diones 5a - r. Compounds 3a - r and 5a - r were evaluated for their antioxidant activity (DPPH free radical scavenging activity).
- Cacic, Milan,Molnar, Maja
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scheme or table
p. 177 - 183
(2011/05/06)
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- A fluorogenic probe for the copper(I)-catalyzed azide-alkyne ligation reaction: Modulation of the fluorescence emission via 3(n, π*)-1(π,π*) inversion
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Chemoselective ligation reactions represent a powerful approach for labeling of proteins or small molecules in a biological environment. We report here a fluorogenic probe that is activated by click chemistry, a highly versatile bio-orthogonal and chemose
- Zhou, Zhen,Fahrni, Christoph J.
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p. 8862 - 8863
(2007/10/03)
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