- One pot, three component 1,3 dipolar cycloaddition: Regio and diastereoselective synthesis of spiropyrrolidinyl indenoquinoxaline derivatives
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A competent and highly discriminating one-pot synthesis of highly diversified novel functionalized indenoquinoxalone grafted spiropyrrolidine linked chromene-3-carbonitrile conjugates accumulating three pharmocophoric cores, heterocyclic indenoquinoxalone, pyrrolidines and chromene-3-carbonitrile in a single molecular framework by means of 1,3-dipolar cycloaddition reaction between indenoquinoxalone, proline/benzyl amine and chromene-3-carbonitrile in ethanol under classical and microwave conditions is described. The three component 1,3-dipolar cycloaddition reaction proceeds via in situ generation of azomethine ylides by the decarboxylative condensation of indenoquinoxalone with proline/benzyl amine and their selectivity towards the endo cyclic double bonds of dipolarophile (chromene-3-carbonitrile) leading to the formation of highly functionalised regio- and diastereoselective molecular hybrids. This methodology exemplifies the green chemistry protocol such as mild reaction conditions, high yields, one-pot procedure and operational simplicity.
- Pattanaik, Priyabrata,Nayak, Sabita,Ranjan Mishra, Deepak,Panda, Pravati,Prasad Raiguru, Bishnu,Priyadarsini Mishra, Nilima,Mohapatra, Seetaram,Arjunreddy Mallampudi,Purohit, Chandra Shekhar
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Read Online
- 10-Camphorsulfonic acid ((±)-CSA) catalyzed facile one-pot synthesis of a new class of 2,5-disubstituted 1,3,4-oxadiazoles
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A convenient and efficient one-pot synthesis of 2,5-disubstituted-1,3,4-oxadizoles is described. Various carboxylic acid hydrazides reacted efficiently with different carboxylic acid chlorides and 10-camphorsulfonic acid. This methodology was successfully
- Mule, Siva Nagi Reddy,Battula, Sailaja Kumari,Velupula, Ganapathi,Guda, Dinneswara Reddy,Bollikolla, Hari Babu
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- A spectroscopic insight into the interaction of chromene 1,2,4-oxadiazole-based compounds with bovine serum albumin
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Four synthesized 2H-chromene-based 1,2,4-oxadiazole compounds (6a-6d) were studied for binding with bovine serum albumin (BSA) by different spectroscopic and thermodynamic analyses. A molecular docking program was used to find out the possible binding sites and binding affinity of 2H-chromene based 1,2,4-oxadiazole compounds with bovine serum albumin (BSA). The intrinsic fluorescence of BSA was quenched by these compounds through static quenching mechanism, and the estimated binding constant (Kb) value was found to be 1.5 × 103–10 × 103. The conformational changes of BSA were monitored by circular dichroism analysis, and it was observed that BSA is structurally stable in the presence of these compounds. The thermodynamic results indicated that the interaction process is spontaneous and the binding between oxadiazole compounds and BSA is mainly driven by hydrogen bonding and van der Waals forces. This study would be helpful to understand the biological benefits of oxadiazole-based compounds as well as the nature of interactions with biomolecules. Graphic abstract: [Figure not available: see fulltext.].
- Mishra, Nilima Priyadarsini,Satish, Lakoji,Mohapatra, Seetaram,Nayak, Sabita,Sahoo, Harekrushna
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- Synthesis and antimicrobial evaluation of novel urea derivatives from chromene based oxadiazole amines
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A series of novel aryl ureides were synthesized based on oxadiazoles and different substituted aromatic amines. The intermediate amine, (3-(2H-chromen-3-yl)-1,2,4-oxadiazol-5-yl)methanamines (6a) was reacted with aromatic amines in presence of triphosgene
- Kumar, K. Santosh,Daniel,Kaki, Shiva Shanker,Rao, Ch. Prasad,Krupadanam, G.L. David
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Read Online
- Synthesis, characterization, and antifungal activity of novel chromene oxadiazole based dithiocarbamates
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A series of novel conjugated chromene oxadiazole-based dithiocarbamate (5a–i) derivatives have been synthesized from oxadiazole (4a–c) intermediates with carbon disulfide. The structures of all the newly synthesized compounds were established by IR, NMR, and Mass spectral analysis. The synthesized derivatives were screened for their antifungal activity against Aspergillus niger fungal strain and the results showed that some of the derivatives were found to exhibit good antifungal activity.
- Bhoga, Srinivas,Gutam, Madhu,Konda, Santosh Kumar,Krupadanam, G. L. David,Mattela, Kutumbarao,Nayaki, Salva Reddy,Thalari, Gangadhar
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supporting information
(2022/03/02)
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- Synthesis of Pharmaceutically Relevant 2-Aminotetralin and 3-Aminochroman Derivatives via Enzymatic Reductive Amination
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2-Aminotetralin and 3-aminochroman derivatives are key structural motifs present in a wide range of pharmaceutically important molecules. Herein, we report an effective biocatalytic approach towards these molecules through the enantioselective reductive coupling of 2-tetralones and 3-chromanones with a diverse range of primary amine partners. Metagenomic imine reductases (IREDs) were employed as the biocatalysts, obtaining high yields and enantiocomplementary selectivity for >15 examples at preparative scale, including the precursors to Ebalzotan, Robalzotan, Alnespirone and 5-OH-DPAT. We also present a convergent chemo-enzymatic total synthesis of the Parkinson's disease therapy Rotigotine in 63 % overall yield and 92 % ee.
- Citoler, Joan,Harawa, Vanessa,Marshall, James R.,Bevinakatti, Han,Finnigan, James D.,Charnock, Simon J.,Turner, Nicholas J.
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supporting information
p. 24456 - 24460
(2021/10/19)
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- Synthesis, cytotoxicity, and molecular docking of substituted 3-(2-methylbenzofuran-3-yl)-5-(phenoxymethyl)-1,2,4-oxadiazoles
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A series of new benzofuran/oxadiazole hybrids (8a–n) was synthesized from 2H-chromene-3-carbonitriles (3a–c) through the multistep synthetic methodology, and these hybrids are known to exhibit anticancer activities. All the compounds were evaluated for their in vitro cytotoxicity against the HCT116 and MIA PaCa2 cell lines. Compounds 6a (IC50: 9.71 ± 1.9 μM), 6b (IC50: 7.48 ± 0.6 μM), and 6c (IC50: 3.27 ± 1.1 μM) displayed a significant cytotoxic activity, whereas compounds 8d and 8e exhibited good activity against both cell lines. The depletion of glycogen synthase kinase-3β (GSK3β) induces apoptosis through the inhibition of basal NF-κB activity in HCT116 colon cancer cells and MIA PaCa2 pancreatic cancer cells. Molecular docking of compounds 6a, 6b, 6c, 8d, and 8e with GSK3β demonstrated the best binding affinity, correlating with the biological activity assay. Furthermore, the structure–activity relationship of these novel compounds reveals promising features for their use in anticancer therapy.
- Mokenapelli, Sudhakar,Thalari, Gangadhar,Vadiyaala, Naveen,Yerrabelli, Jayaprakash R.,Irlapati, Vamshi K.,Gorityala, Neelima,Sagurthi, Someswar R.,Chitneni, Prasad R.
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- Design and Synthesis of Novel 2-Substituted-Benzyl-5-(2-Methylbenzofuran-3-yl)-2H-Tetrazoles: Anti-Proliferative Activity
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Abstract: A new series of 2,5-regioselective benzofuran-tetrazole hybrids (XIIIa–XIIIp) were synthesised from 2H-chromene-3-carbonitriles (IXa), (IXb) in multi steps approach under mild reaction conditions in good yields and evaluated their anti-proliferative activity against HCT116 and Miapaca2 cell lines. Wherein compounds (XIIIe) (IC50: 3.19 μM) and (XIIIm) (IC50: 2.25 μM) were displayed highest anti-proliferative activity in both cell lines. Molecular docking and SAR studies revealed the in vitro results with target Proto-oncogene tyrosine kinase Src protein.
- Chitneni, Prasad Rao,Gorityala, Neelima,Gutam, Madhu,Irlapati, Vamshi Krishna,Sagurthi, Someswar Rao,Sudhakar, Mokenapelli,Yerrabelli, Jayaprakash Rao
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p. 845 - 855
(2020/10/29)
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- Microwave-Assisted Rapid and Efficient Synthesis of New Series of Chromene-Based 1,2,4-Oxadiazole Derivatives and Evaluation of Antibacterial Activity with Molecular Docking Investigation
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A new series of novel chromene-based oxadiazole derivatives were synthesized from a variety of chromene-based amidoximes with readily available carboxylic acids under conventional oil bath heating as well as under microwave irradiation. The use of commercially available EDCI and HOBt as coupling reagents in DMF combined with microwave heating resulted in high yields and purities of the product 1,2,4-oxadiazoles in an expeditious manner. This methodology is successfully applied to synthesize 18 numbers of new 2H-chromene-substituted 1,2,4-oxadiazole derivatives in good to high yields. The structure of the product was ascertained by X-ray crystallographic analysis. All the synthesized compounds were evaluated for their in vitro antibacterial activity against two different pathogenic bacterial strains, that is, Escherichia coli (MTCC614) and Klebsiella pneumoniae (MTCC4031). The obtained results from in vitro antimicrobial assays indicated that 6g and 6h exhibited good antibacterial activity nearer to the standard drug, gentamicin. The molecular docking studies showed that compounds 6g and 6h show hydrogen bonding interaction with the bacterial target DNA gyrase of E.?coli.
- Baral, Nilofar,Mohapatra, Seetaram,Raiguru, Bishnu Prasad,Mishra, Nilima Priyadarsini,Panda, Pravati,Nayak, Sabita,Pandey, Satyendra Kumar,Kumar, P. Sudhir,Sahoo, Chita Ranjan
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p. 552 - 565
(2019/01/04)
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- Discovery of (S)-6-methoxy-chroman-3-carboxylic acid (4-pyridin-4-yl-phenyl)-amide as potent and isoform selective ROCK2 inhibitors
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ROCK1 and ROCK2 are highly homologous isoforms. Accumulated studies indicate that they have distinct different functions, and the development of isoform selective ROCK inhibitors will pave new roads for the treatment of various diseases. In this work, a series of amide-chroman derivatives were synthesized and biologically evaluated in order to develop potent and isoform selective ROCK2 inhibitors. Remarkably, (S)-6-methoxy-chroman-3-carboxylic acid (4-pyridin-4-yl-phenyl)-amide ((S)-7c) possessed ROCK2 inhibitory activity with an IC50 value of 3 nM and 22.7-fold isoform selectivity (vs. ROCK1). Molecular docking indicated that hydrophobic interactions were the key element for the high potency and isoform selectivity of (S)-7c. The binding free energies predicted by MM/GBSA were in good agreement with the experimental bioactivities, and the analysis of individual energy terms suggested that residue Lys105 in ROCK1 or Lys121 in ROCK2 was the key residue for the isoform selectivity of (S)-7c.
- Pan, Jinpeng,Yin, Yan,Zhao, Lianhua,Feng, Yangbo
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p. 1382 - 1390
(2019/02/26)
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- DUAL AGONISTS OF FXR AND PPARδ AND THEIR USES
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The present invention relates to small molecule compounds and their use as agonists of farnesoid X receptor (FXR) and/or peroxisome proliferator activated receptor delta (PPARδ). The present invention also relates to the use of said compounds in the treatment of metabolic diseases and respective methods of treatment.
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(2019/04/16)
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- COMPOUNS, COMPOSITIONS AND METHODS OF USE
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Herein, compounds, compositions and methods for modulating inclusion formation and stress granules in cells related to the onset of neurodegenerative diseases, musculoskeletal diseases, cancer, ophthalmological diseases, and viral infections are described.
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Page/Page column 191
(2018/07/29)
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- Benzopyrans compound as well as preparation method and application thereof
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The invention relates to the field of the agricultural fungicide, and specifically relates to a benzopyrans compound as well as a preparation method and application thereof. The benzopyrans compound provided by the invention is simple in structure, easy to synthesize, low in production cost, and has a good inhibiting effect on the strawberry botrytis cinerea, potato altemaria solani, and watermelon fusarium oxysporum.
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Paragraph 0095-0099
(2018/11/27)
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- Bifunctional Br?nsted Base Catalyst Enables Regio-, Diastereo-, and Enantioselective Cα-Alkylation of β-Tetralones and Related Aromatic-Ring-Fused Cycloalkanones
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The catalytic asymmetric synthesis of both α-substituted and α,α-disubstituted (quaternary) β-tetralones through direct α-functionalization of the corresponding β-tetralone precursor remains elusive. A designed Br?nsted base-squaramide bifunctional catalyst promotes the conjugate addition of either unsubstituted or α-monosubstituted β-tetralones to nitroalkenes. Under these reaction conditions, not only enolization, and thus functionalization, occurs at the α-carbon atom of the β-tetralone exclusively, but adducts including all-carbon quaternary centers are also formed in highly diastereo- and enantioselective manner.
- Urruzuno, I?aki,Mugica, Odei,Oiarbide, Mikel,Palomo, Claudio
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supporting information
p. 2059 - 2063
(2017/02/15)
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- Ruthenium-Catalyzed Oxidative Annulation and Hydroarylation of Chromene-3-carboxamides with Alkynes via Double C-H Functionalization
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Ruthenium-catalyzed oxidative annulation of 2H-chromene-3-carboxamides with alkynes has been achieved by using the directing group nature of amide in the presence of Cu(OAc)2·H2O as an oxidant and AgNTf2 as an additive. This reaction offers a broad substrate scope, and both symmetrical and unsymmetrical alkynes can be harnessed. High regioselectivity was achieved in the case of unsymmetrical alkynes. In addition, we have also accomplished double C-H activation by employing an excess of alkyne, where both annulation and hydroarylation took place regio- and stereoselectively in one pot, with the catalyst playing a dual role. While the first C-H functionalization could involve Ru-N covalent bond, the second C-H functionalization most likely involves Ru-O coordinate bond. The structures of key products are confirmed by X-ray crystallography.
- Tulichala, R. N. Prasad,Shankar, Mallepalli,Swamy, K. C. Kumara
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p. 5068 - 5079
(2017/05/24)
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- Design and synthesis of chiral 2H-chromene-N-imidazolo-amino acid conjugates as aldose reductase inhibitors
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Aldose reductase (ALR2) inhibitors provide a viable mode to fight against diabetic complications. ALR2 exhibit plasticity in the active site vicinities and possible shifts in the nearby two supporting alpha helices. Therefore, a novel series of amino acid conjugates of chromene-3-imidazoles (13–15) were designed and synthesized based on natural isoflavonoids. The compounds were identified on the basis of spectral (1H NMR,13C NMR and MS) data and tested in vitro for ALR2 inhibitory activity with an IC50value ranges from 0.031 ± 0.082 μM to 4.29 ± 0.55 μM. Our in silico and biochemical studies confirmed that 15e has the best inhibition activity among the synthesized compounds with a high selective index against the Aldehyde reductase (ALR1). Supplementation of 15e to STZ induced rats decreased the blood glucose levels and delayed the progression of cataract in a dose-dependent manner. The present study thus provides novel series of compounds with a promising inhibitor to prevent or delay the cataract progression.
- Gopinath, Gudipudi,Sankeshi, Venu,perugu, Shaym,Alaparthi, Malini D.,Bandaru, Srinivas,Pasala, Vijay K.,Chittineni, Prasad Rao,Krupadanam, G.L.David,Sagurthi, Someswar R.
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p. 750 - 762
(2016/09/23)
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- POTENT SMALL MOLECULE INHIBITORS OF AUTOPHAGY, AND METHODS OF USE THEREOF
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Certain aspects of the invention relate to small molecule autophagy inhibitors, and their use for treatment and prevention of cancers and acute pancreatitis. Medicinal chemistry studies led to small molecular autophagy inhibitors with improved potency and selectivity.
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Page/Page column 116; 117
(2014/09/29)
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- Rational design and synthesis of novel 2-(substituted-2H-chromen-3-yl)-5-aryl-1H-imidazole derivatives as an anti-angiogenesis and anti-cancer agent
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Based on earlier proven pharmacophore analogues of cancer a novel 2-(substituted-2H-chromen-3-yl)-5-aryl-1H-imidazoles (13-16) were rationally designed and synthesized by the reaction of chromene-3-carboxylic acids (10a-d) with substituted acyl bromides in the presence of TEA followed by refluxing with NH4OAc in toluene. Compounds 13-16 were screened in vitro for the inhibition of KRAS/Wnt and their anti-angiogenesis properties. Compound 16f has been identified as a potent anti-angiogenesis molecule, which can be considered as a new lead structure. The molecular docking analysis displayed the higher binding affinity of 16f with KRAS, Wnt and VEGF.
- Gudipudi, Gopinath,Sagurthi, Someswar R.,Perugu, Shyam,Achaiah,Krupadanam, G. L. David
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p. 56489 - 56501
(2015/02/05)
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- Iridium-catalyzed enantioselective hydrogenation of unsaturated heterocyclic acids
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Spiral binding: A highly enantioselective hydrogenation of unsaturated heterocyclic acids has been developed by using chiral iridium/spirophosphino oxazoline catalysts (see scheme; BArF-=tetrakis[3,5- bis(trifluoromethyl)phenyl]borate, Boc=tert-butoxycarbonyl). This reaction provided an efficient method for the preparation of optically active heterocyclic acids with excellent enantioselectivities. Copyright
- Song, Song,Zhu, Shou-Fei,Pu, Liu-Yang,Zhou, Qi-Lin
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supporting information
p. 6072 - 6075
(2013/07/05)
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- METHOD FOR PREPARING A COUMARIN COMPOUND, CHROMENE COMPOUND, AND METHOD FOR PREPARING A CHROMENE COMPOUND
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Disclosed herein is a method for preparing a coumarin compound of formula (F), in which R1, R2, and R3 are independently H, C1?C7 alkoxy, C1?C7 alkyl, phenoxy, benzyloxy, or a ha
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Page/Page column 4-5
(2012/04/18)
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- NOVEL CHROMENE AND THIOCHROMENE CARBOXAMIDE DERIVATIVES, METHODS FOR PREPARING SAME AND THERAPEUTIC APPLICATIONS OF SAME
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The present invention relates to novel chromene or thiochromene carboxamide derivatives, the preparation of same, pharmaceutical compositions of same and the use of same as dopamine D3 ligands as a medicament for central nervous system disorders.
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Page/Page column 24
(2008/06/13)
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- ANTAGONISTS OF THE TRPV1 RECEPTOR AND USES THEREOF
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The present application is directed to compounds that are TRPV1 antagonists and have formula (I) wherein variables Ar1, L1, R1, R2, R3, R4, R5, Y1, Y2, and Y3, are as defined in the description, which are useful for treating disorders caused by or exacerbated by vanilloid receptor activity.
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Page/Page column 13
(2008/12/06)
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- Conformationally restricted anti-plasmodial chalcones
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Chalcones can exist as Z- or E-isomers and it is generally anticipated that both isomers are equipotent. In order to determine the active isomer of anti-plasmodial chalcones a series of analogues locked in the Z- or the E-form were prepared and evaluated
- Larsen, Mogens,Kromann, Hasse,Kharazmi, Arsalan,Nielsen, Simon Feldbaek
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p. 4858 - 4861
(2007/10/03)
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- Compounds that modulate PPAR activity and methods of preparation
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This invention discloses compounds that alter PPAR activity. The invention also discloses pharmaceutically acceptable salts of the compounds, pharmaceutically acceptable compositions comprising the compounds or their salts, and methods of using them as therapeutic agents for treating or preventing hyperlipidemia and hypercholesteremia in a mammal. The present invention also discloses method for making the disclosed compounds.
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- A convenient general synthesis of 3-substituted 2H-chromene derivatives
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Reactions of 2-hydroxybenzaldehydes and 2-hydroxy-1-naphthaldehydes with various activated alkenes under Baylis-Hillman conditions have been shown to proceed with regioselective cyclisation to afford the corresponding 3-substituted chromene derivatives. In some cases competitive dimerisation of the alkene component was observed, and direct dimerisation in the absence of the aldehyde has been explored.
- Kaye, Perry T.,Nocanda, Xolani W.
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p. 1318 - 1323
(2007/10/03)
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- A new approach to the synthesis of chromene derivatives
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3-Acetyl-5,6-benzopyran and 3-benzoyl-5,6-benzopyran have been simply prepared by condensation of methylvinyl ketone and phenylvinyl ketone with salicylaldehyde in an aqueous DABCO medium at room temperature.
- Ravichandran
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p. 1233 - 1235
(2007/10/03)
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- Efficient syntheses of new heteroarotinoids through functional pyridylzinc reagents and palladium-catalyzed cross-coupling reactions
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A convergent synthesis of heteroarotinoids 4, 5a, and 5b, bearing chromene rings in association with pyridyl or ethynylpyridyl moieties, from 6-bromo-2-pyridylzinc chloride (11) is described. This new functional heteroarylzinc reagent, readily accessible
- Alami, Mouad,Peyrat, Jean-Francois,Belachmi, Larbi,Brion, Jean-Daniel
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p. 4207 - 4212
(2007/10/03)
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- Synthesis, biological activity and quantitative structure-activity relationships of N-substituted-3,4-dihydro-2H-1-benzopyran derivatives
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Synthesis of N-substituted-3,4-dihydro-2H-l-benzopyran derivatives which have a potential affinity for the 5-HT(1A) receptor is reported. The comparison between the experimental values of binding and the prediction of Q.S.A.R. studies is described.
- Marot,Comoy,Viaud,Rettori,Pfeiffer,Morin-Allory,Guillaumet
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p. 1077 - 1082
(2007/10/03)
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- Dabco-catalysed reactions of salicylaldehydes with acrylate derivatives
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Treatment of salicylaldehydes with acrylate derivatives in the presence of 1,4-diazabicyclo[2.2.2]octane (DABCO) has been shown to afford both coumarin and chromene derivatives, and factors influencing the product distributions have been investigated.
- Kaye, Perry T.,Robinson, Ross S.
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p. 2085 - 2097
(2007/10/03)
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- Pharmacomodulation d'adrenolytiques α en serie benzopyrannique
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Pharmacomodulation of α-adrenergic blocking agents by a series of benzopyrans.The N-methylpiperidine fragment was associated with four oxygenated heterocycles of the benzopyran ring system.Two different synthesis pathways were used in each case.Twenty intermediate derivatives and four aminomethylated derivatives whose structures were established by spectroscopic data are described.The pharmacological investigation demonstrates the interest of these compounds on the α-adrenergic receptors in light of their activities and selectivities. α1-adrenergic blocking agents / α2-adrenergic blocking agents / piperidinomethyl chromone, chromene and chromane
- Mouysset, Genevieve,Payard, Marc,Grassy, Gerard,Tronche, Pierre,Dabire, Hubert,et al.
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p. 539 - 544
(2007/10/02)
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- Chromene and Chroman 3-Carboxamides and Some Related Compounds as a New Class of Centrally Acting Agents
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A number of chromene-3-carboxamides (7), 3-Aminochromans (11) and 3-aminomethylchromans (9) have been synthesized.Chromene-3-carboxamides have been found to exhibit strong central muscle relaxant activity compared to mephesin.
- Gupta, R. C.,Pratap, Ram,Prasad, C. R.,Anand, Nitya
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p. 344 - 347
(2007/10/02)
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