- Intramolecular cyclisation of functionalised heteroaryllithiums. Synthesis of novel indolizinone-based compounds
-
The intramolecular cyclisation of heteroaryllithiums derived from N-heteroarylmethylpyrrole-2-carboxamides takes place smoothly at low temperature when N-methoxy-N-methyl and morpholine amides are used as internal electrophiles. Halogen-lithium exchange using n-BuLi is the method of choice to achieve metalation on the quinoline and pyridine derivatives, while directed lithiation (LDA) works better for furan. In the case of thiophene both methodologies can be applied. These metalation-cyclisation sequences provide a useful entry to several types of indolizidine based compounds (pyrrolo[1,2-b]acridinones, pyrrolo[1,2-g]quinolones, thieno and furo[3,2-f]indolizinones).
- Ruiz, Javier,Lete, Esther,Sotomayor, Nuria
-
-
Read Online
- Expeditious Synthesis of the Topoisomerase i Inhibitors Isoindolo[2,1- b ]isoquinolin-7(5 H)-one and the Alkaloid Rosettacin Based on Aryl Radical Cyclization of Enamide Generated by Using N -Acylaiminium Chemistry
-
A short and effective approach to the synthesis of the topoisomerase I inhibitor isoindolo[2,1-b]isoquinolin-7(5H)-one and the alkaloid rosettacin belonging to the aromathecin family is presented. The key step of this sequence, which resulted in the formation of a five-membered ring, was the aryl radical cyclization of enamides generated using N-acyliminium chemistry.
- El Blidi, Lahssen,Namoune, Aurélie,Bridoux, Alexandre,Nimbarte, Vijaykumar D.,Lawson, Ata Martin,Comesse, Sébastien,Da?ch, Adam
-
-
Read Online
- ZnO nanoparticles in the synthesis of AB ring core of camptothecin
-
For the first time, synthesis of AB ring core of camptothecin synthons such as (2-chloroquinolin-3-yl)methanols (Va-Vg) using zinc oxide nanoparticles is reported. The desired attractive products were obtained in high yields, short reaction time, using a simple work-up procedure with the purification of products by non-chromatographic methods.
- Roopan, Selvaraj Mohana,Nawaz Khan, Fazlur Rahman
-
-
Read Online
- Friedel-Crafts Chemistry. Part 48. Concise Synthesis of Condensed Azaheterocyclic [1,8]naphthyridinones, Azepino-, Azocino-, and Azoninoquinoline Systems via Friedel-Crafts Ring Closures
-
Unprecedented construction of a novel series of quinoline heteropolycycles (tetracyclic keto-analogues of [1,8]naphthyridinones, azepino-, azocino-A nd azonino[2,3-b]quinolinones systems) 10a-i by Friedel-Crafts cycliacylation reactions is described. Starting heterocyclic acids precursors 3a-i were prepared from easily accessible 2-chloroquinoline-3-carbaldehyde 1 via a three different synthetic pathways. Acid-catalyzed ring closures of the resulting tosylated acids were achieved under the influence of both Br?nsted and Lewis acid catalysts. The present strategy enables a straightforward synthesis to fused tetracyclic quinolinone skeletons as demonstrated by concise and atom-economical syntheses.
- Abd El-Aal, Hassan A. K.
-
-
Read Online
- Quinoline and 2-nitroimino-1, 3-diazacycloalkane hybrids: Design, synthesis and insecticidal activity
-
A library of new hybrid molecules comprising quinoline, 2-nitroimino-1, 3-diazacycloalkane motifs were designed and synthesized as plausible neonicotinoid analogues. These compounds were synthesized from 2-chloro/aryloxy-3-formyl quinolines and guanidine nitrate with the coupling of 2-chloro/aryloxy-3-(chloromethyl)quinolines, 2-nitroimino-1, 3-diazacycloalkanes under phase transfer catalysis (PTC) as crucial step. All the compounds were obtained in excellent yields (80–90%) and were characterized by 1H, 13C NMR and mass spectrometry. The newly generated compounds were screened for insecticidal activity against aphids in safflower field and some of them displayed moderate activity.
- Sowmya, Jonnalagadda,Padma, Banda,Leelavathi, Panaganti
-
-
- Design, synthesis and biological evaluation of mono- and bisquinoline methanamine derivatives as potential antiplasmodial agents
-
Several classes of antimalarial drugs are currently available, although issues of toxicity and the emergence of drug resistant malaria parasites have reduced their overall therapeutic efficiency. Quinoline based antiplasmodial drugs have unequivocally been long-established and continue to inspire the design of new antimalarial agents. Herein, a series of mono- and bisquinoline methanamine derivatives were synthesised through sequential steps; Vilsmeier-Haack, reductive amination, and nucleophilic substitution, and obtained in low to excellent yields. The resulting compounds were investigated for in vitro antiplasmodial activity against the 3D7 chloroquine-sensitive strain of Plasmodium falciparum, and compounds 40 and 59 emerged as the most promising with IC50 values of 0.23 and 0.93 μM, respectively. The most promising compounds were also evaluated in silico by molecular docking protocols for binding affinity to the {0 0 1} fast-growing face of a hemozoin crystal model.
- Bokosi, Fostino R.B.,Beteck, Richard M.,Mbaba, Mziyanda,Mtshare, Thanduxolo E.,Laming, Dustin,Hoppe, Heinrich C.,Khanye, Setshaba D.
-
-
- Microwave assisted regioselective synthesis of quinoline appended triazoles as potent anti-tubercular and antifungal agents via copper (I) catalyzed cycloaddition
-
Quinolin-3-yl-methyl-1,2,3-triazolyl-1,2,4-triazol-3(4H)-ones 8j-v were synthesized by click chemistry as an ultimate tactic where [3 + 2] cycloaddition of azides with terminal alkynes has been evolved. Herein, we are inclined to divulge the implication and prevalence of CuSO4·5H2O and THF/water promoted [3 + 2] cycloaddition reactions. The foremost supremacy of this method are transitory reaction times, facile workup, excellent yields (88–92%) with exorbitant purity and regioselective single product formation both under conventional and microwave method. Docking studies illustrated strong binding interactions with enzyme InhA-D148G (PDB ID: 4DQU) by means of high C-score values. The anti-tubercular and antifungal screening of synthesized compounds proclaimed promising activity. The in vitro and in silico studies imply that these triazoles appended quinolines may acquire the ideal structural prerequisites for auxiliary expansion of novel therapeutic agents.
- Nesaragi, Aravind R.,Kamble, Ravindra R.,Bayannavar, Praveen K.,Shaikh, Saba Kauser J.,Hoolageri, Swati R.,Kodasi, Barnabas,Joshi, Shrinivas D.,Kumbar, Vijay M.
-
-
- Design, Synthesis, and Antifungal Evaluation of Luotonin A Derivatives against Phytopathogenic Fungi
-
Crop diseases caused by fungi threaten food security and exacerbate the food crisis. Inspired by the application of fungicide candidates from natural products in agrochemical discovery, a series of luotonin A derivatives were designed, synthesized, and evaluated for their antifungal activities against five plant fungi. Most of these compounds exhibited significant fungicidal activity against Botrytis cinerea in vitro with EC50 values less than 1 μg/mL. Among them, compounds w7, w8, w12, and w15 showed superior antifungal activity against B. cinerea with EC50 values of 0.036, 0.050, 0.042, and 0.048 μg/mL, respectively, which were more potent than boscalid (EC50 = 1.790 μg/mL). Preliminary mechanism studies revealed that compound w7 might pursue its antifungal activity by disrupting the fungal cell membrane and cell wall. Moreover, in vivo bioassay also indicated that compound w7 could be effective for the control of B. cinerea. The above results evidenced the potential of luotonin A derivatives as novel and promising candidate fungicides.
- Chu, Qing-Ru,Du, Sha-Sha,He, Ying-Hui,Li, Hai-Xing,Liu, Ying-Qian,Tang, Chen,Wang, Jing-Ru,Wang, Ren-Xuan,Wu, Tian-Lin,Yang, Cheng-Jie,Zhang, Zhi-Jun
-
p. 14467 - 14477
(2021/12/09)
-
- Interrupting the Barton?McCombie reaction: Aqueous deoxygenative trifluoromethylation of o-alkyl thiocarbonates
-
The site-selective trifluoromethylation of aliphatic systems remains an important challenge. This work describes a light-driven, copper-mediated trifluoromethylation of O-alkyl thiocarbonates. The reaction provides broad functional group tolerance (e.g., alkyne, alkene, phenol, free alcohol, electron-rich and -deficient arenes), thereby offering orthogonality and practicality for trifluoromethylation. A radical organometallic mechanism is proposed.
- Liu, Zhi-Yun,Cook, Silas P.
-
supporting information
p. 808 - 813
(2021/02/01)
-
- Microwave assisted synthesis of quinoline fused benzodiazepines as anxiolytic and antimicrobial agents
-
In the present study, an efficient, facile and green protocol for synthesis of quinoline fused 1,4-benzodiazepine (4a-j) by microwave irradiated condensation of 6/7/8-substituted 3-bromomethyl-2-chloro-quinoline (3a-j) obtained from 2-chloro 6/7/8-substituted quinoline-3-carbaldehyde (1a-j) with 1, 2-phenylenediamine was developed. Surflex docking studies with K+ channel is one of the physiological targets and inhibition, which plays a role in the pathophysiology of depression revealed that all these compounds show consensus score in the range 2.71-3.68 indicating the summary of all forces of interaction. Further, compounds 4d, 4g and 4i exhibited potent antibacterial activity.
- Marganakop,Kamble,Nesaragi,Bayannavar,Joshi,Kattimani,Sudha
-
p. 1107 - 1114
(2021/05/10)
-
- Chemoselective transfer hydrogenation of aromatic and heterocyclic aldehydes by green chemically prepared cobalt oxide nanoparticles
-
A new surfactant (quercetin) assisted hydrothermal method is used for the preparation of phase pure cobalt oxide (Co3O4) nanoparticles (Nps). The quercetin acted well as surfactant in producing size controlled Nps. The produced Nps were extensively characterized by various techniques to reveal its chemical composition, structure, morphology, size and thermal behavior. The main objective of the study is to employ the prepared material as heterogeneous catalyst for hydrogenation of therapeutically important aldehydes. The capability of the catalyst is appear to be good, since the yield of alcohols from structurally different aldehydes is adequate with short period of time. Also the catalyst is recyclable, stable, no need of addition of ligands for activation and environmentally benign.
- Krishnaveni,Lakshmi,Kaveri,Kadirvelu
-
-
- Convenient synthesis of quinoline-fused triazolo-azepine/oxepine derivatives through Pd-catalyzed C-H functionalisation of triazoles
-
The efficient and convenient synthesis of a new fused heterocyclic scaffold comprising three different heterocycles, viz., quinolines, azepines/oxepines and triazoles is reported from quinoline-tethered triazoles. The quinoline-tethered triazoles were eas
- Mahesh, Kukkamudi,Ravi, Kanakaraju,Rathod, Praveen Kumar,Leelavathi, Panaganti
-
p. 2367 - 2373
(2020/02/20)
-
- Triazolothiadizepinylquinolines as potential MetAP-2 and NMT inhibitors: Microwave-assisted synthesis, pharmacological evaluation and molecular docking studies
-
The enzymes MetAP-2 and NMT play a crucial role in the process of myristoylation of oncoproteins which is deregulated in many types of cancers. Execution of both these enzymes is considered as strategy for the intervention of various cancers and relative fungal infections, and hence the discovery of novel MetAP-2 and NMT inhibitors necessitate their high relevancy. In this investigation, we have synthesized a series of novel seven-membered triazolothiadiazepinyl quinolines 10(a–m) distinctively under microwave irradiation technique and identified as selective MetAP-2 and NMT inhibitors. Amongst the functionalized derivatives when evaluated for the in vitro antifungal assay, compounds 10b, 10c, 10e and 10f were considered promising due to notable inhibitory effects (MIC = 0.2 mg/mL) on Aspergillus fumigatus. Screening of the anticancer activity against NCI-60 Human tumor cell lines portrayed that conjugates 10b, 10c, 10e and 10f were found to be moderately effective against the Renal Cancer cell line UO-31. The data acquired from biological studies was further validated by molecular docking studies and pharmacokinetic evaluation.
- Shaikh, Saba Kauser J.,Kamble, Ravindra R.,Bayannavar, Praveen K.,Somagond, Shilpa M.,Joshi, Shrinivas D.
-
-
- Facile Synthesis of 2-Acylthieno[2,3- b]quinolines via Cu-TEMPO-Catalyzed Dehydrogenation, sp2-C-H Functionalization (Nucleophilic Thiolation by S8) of 2-Haloquinolinyl Ketones
-
An efficient, solvent-free synthesis of 2-acylthieno[2,3-b]quinolines is reported from 2-halo-quinolinyl ketones through Cu-TEMPO catalyzed dehydrogenation, sp2-C-H functionalization using elemental sulfur as thiol surrogate (sulfur source) and tetrabutylammonium acetate as an ionic reaction medium. The optimized reaction conditions give excellent product yields under mild reaction conditions with chemoselectivity and broad functional group tolerance. The synthetic importance of the synthesized molecules is showcased further by Friedl?nder annulation, reduction, and alkene functionalization reactions.
- Nawaz Khan, Fazlur Rahman,Teja, Chitrala
-
supporting information
p. 1726 - 1730
(2020/03/24)
-
- RETRACTED ARTICLE: Synthesis, Molecular Properties, and Biological Evaluation of Hybrid 1,2,3-Triazolylpolyaza Heterocyclic Compounds
-
In this research article, a highly efficient, cost-effective synthesis of various hybrid molecules possessing 1,2,3-triazolyltetrazoles and evaluation of their biological activity have been addressed. The structure elucidation of these new library hybrid molecules has been carried out by IR, 1H NMR, 13C NMR, and mass spectral analysis. The compounds have been screened for their anticancer activity against human colon cancer cell line Colo-205 and human lung cancer cell line HOP-205, and the results attest that most of the compounds have shown very good therapeutic nature. In particular, compounds 3d, 3j, 6a, and 6e were more cytotoxic than Adriamycin against all tested human cancer cell lines with 68percent, 101.8percent, 94percent, and 104.5percent growth, respectively. In the present investigation, a series of 3a–j and 6a–h were subjected to molecular properties prediction, drug likeness by Molinspiration, and toxicity risks by Molsoft software programs. All the 18 analogues were chosen on the basis of Lipinski “Rule of five” for the synthesis, screening their antibacterial and anticancer as oral bioavailable drugs/leads.
- Dasari, Srinivasa Rao,Tondepu, Subbaiah,Vadali, Lakshmana Rao,Ganivada, Mutyala Naidu,Seelam, Nareshvarma
-
p. 195 - 208
(2019/01/04)
-
- Intermolecular interactions in molecular crystals and their effect on thermally activated delayed fluorescence of helicene-based emitters
-
Here, we discuss the influence of the crystal structure on the photophysical properties of two new TADF emitters containing a non-planar helical moiety. The presence of solvent in the crystal lattice of a diaza[5]helicene-based compound alters molecular p
- Klimash, Anastasia,Pander, Piotr,Klooster, Wim T.,Coles, Simon J.,Data, Przemyslaw,Dias, Fernando B.,Skabara, Peter J.
-
supporting information
p. 10557 - 10568
(2018/10/24)
-
- Tetrazolylmethyl quinolines: Design, docking studies, synthesis, anticancer and antifungal analyses
-
A new series of 2,5 and 1,5-regioisomers of the tetrazolyl group viz., 3-[(5-benzyl/benzylthio-2H-tetrazol-2-yl) methyl]-2-chloro-6-substituted quinoline 6h-q and 3-[(5-benzyl/benzylthio-1H-tetrazol-1-yl) methyl]-2-chloro-6-substituted quinolines 7h-q were synthesized. Docking studies of all these compounds with DNA as target using PDB: 1AU5 and 453D revealed that the compounds 6h and 6i act as covalent cross linker on the DNA helix of the former and intercalate the latter both with higher C score values. Another set of docking studies in the active pocket of dihydrofolate reductase and N-myristoyl transferase as targets to assess antifungal activity revealed that compounds 6k, 6l, 6p and 7q (with bromo and fluro substituents) showcases different binding modes and hydrogen bonding. Further, the compounds were screened for anticancer activity (primary cytotoxicity) against NCI-60 Human tumor cell line at a single high dose (10?5M) concentration assay. Among the tested compounds, 6h has shown 99.28% of GI against Melanoma (SK-MEL-5) and compound 6i has shown 97.56% of GI against Breast Cancer (T-47D). Further, in vitro antifungal assay against A. fumigatus and C. albicans for these compounds 6h-q and 7h-q revealed potential to moderate activities as compared to the standard.
- Shaikh, Saba Kauser J.,Kamble, Ravindra R.,Somagond, Shilpa M.,Devarajegowda,Dixit, Sheshagiri R.,Joshi, Shrinivas D.
-
p. 258 - 273
(2017/02/15)
-
- Highly efficient reduction of carbonyls, azides, and benzyl halides by NaBH4 in water catalyzed by PANF-immobilized quaternary ammonium salts
-
A series of polyacrylonitrile fiber-supported quaternary ammonium salts (PANF-QAS) were prepared and applied to the catalytic reduction of aldehydes, ketones, azides, and benzyl halides in water using NaBH4 as the reducing reagent in a highly efficient, economic, and environmentally benign way. The structure-activity relationships were investigated, which showed that the catalysts made up of quaternary ammonium salts with longer alkyl chains, larger cationic radii and better lipophilicity speed up the reduction reaction to afford the products in excellent yield. Moreover, the optimized catalyst can be applied to the reduction of 1-naphthaldehyde in a continuous flow process with outstanding reactivity and recyclability.
- Du, Jianguo,Xu, Gang,Lin, Huikun,Wang, Guangwei,Tao, Minli,Zhang, Wenqin
-
supporting information
p. 2726 - 2735
(2016/05/24)
-
- Total Synthesis of Camptothecin and Related Natural Products by a Flexible Strategy
-
A flexible strategy for constructing natural products containing indolizinone or quinolizinone scaffolds and their analogues was developed, which was based on a cascade exo hydroamination followed by spontaneous lactamization. This method was applied in the total synthesis of camptothecin in nine steps in a new ring-forming approach. It was also used to efficiently prepare five biogenetically or structurally related natural alkaloids, including 22-hydroxyacuminatine, oxypalmatine, norketoyobyrine, naucleficine, and nauclefine, as well as 35 natural-product-like molecules. We believe that this method and the small-molecule library prepared with it can open new avenues for studying the bioactivity of camptothecin and Nauclea natural products.
- Li, Ke,Ou, Jinjie,Gao, Shuanhu
-
supporting information
p. 14778 - 14783
(2016/11/23)
-
- SORAFENIB ANALOGS AND USES THEREOF
-
The present invention provides, inter alia, compounds according to formula I. Also provided are pharmaceutical compositions and kits containing such compounds. Methods for using such compounds, compositions, and kits for treating a subject having system xc-, dysregulation for activating ferroptosis, for inhibiting system xc- in a cell, and for monitoring treatment of a subject having system xc- dysregulation are provided as well.
- -
-
-
- Design of new hybrid template by linking quinoline, triazole and dihydroquinoline pharmacophoric groups: A greener approach to novel polyazaheterocycles as cytotoxic agents
-
A new hybrid template designed by linking three pharmacophoric groups, for example, quinoline, triazole and dihydroquinoline moieties have been used for the generation of a library of molecules as potential cytotoxic agents. Synthesis of these polyazaheterocycles were carried out by using a strategy that involved one-pot sequential azidation and CuAAC in water under mild conditions. A number of 1,4-disubstituted 1,2,3-triazoles possessing quinolinylmethylene at N-1 and 1,2-dihydroquinolinyl methylene at C-4 as different substituents were synthesized and evaluated for their cytotoxic effects against various cancer cells. Some of them showed encouraging activities against lung cancer cells and one of them showed inhibition of PDE4 indicating the potential medicinal value of these novel polyazaheterocycles.
- Praveena, Koduru Sri Shanthi,Shivaji Ramarao, Edupuganti Veera Venkat,Murthy, Nandula Yadagiri Sreenivasa,Akkenapally, Surekha,Ganesh Kumar,Kapavarapu, Ravikumar,Pal, Sarbani
-
p. 1063 - 1069
(2015/02/19)
-
- Enantioselective Palladium-Catalyzed Heck-Heck Cascade Reactions: Ready Access to the Tetracyclic Core of Lycorane Alkaloids
-
A rapid and efficient access to a wide variety of enantiomerically enriched C-11b substituted lycorane analogues can be achieved via a catalytic asymmetric Heck-Heck 6-exo/6-endo cascade reaction in the presence of (R)-BINAP.
- Coya, Estibaliz,Sotomayor, Nuria,Lete, Esther
-
supporting information
p. 3206 - 3214
(2015/11/03)
-
- Novel 1,3,4-oxadiazole motifs bearing a quinoline nucleus: Synthesis, characterization and biological evaluation of their antimicrobial, antitubercular, antimalarial and cytotoxic activities
-
A series of quinoline based 1,3,4-oxadiazole derivatives (8a-l) were synthesized by a chloro-amine coupling reaction approach with different catalysts and solvents. Substituted 1,3,4-oxadiazole intermediates 7a-c were obtained from 2-substituted-N-phenylh
- Ladani, Gaurav G.,Patel, Manish P.
-
p. 9848 - 9857
(2015/12/01)
-
- Synthesis, crystal structure, ABTS radical-scavenging activity, antimicrobial and docking studies of some novel quinoline derivatives
-
In this study, a series of nine novel 2-chloroquinolin-3-yl ester derivatives have been synthesized via a two-step protocol from 2-chloroquinoline-3-carbaldehyde. The structures of all these compounds were confirmed by spectral data. The single crystal X-
- Tabassum, Sumaiya,Suresha Kumara,Jasinski, Jerry P.,Millikan, Sean P.,Yathirajan,Sujan Ganapathy,Sowmya,More, Sunil S.,Nagendrappa, Gopalpur,Kaur, Manpreet,Jose, Gilish
-
-
- Preparation and reactions of heteroarylmethylzinc reagents
-
We report a general preparation of heteroarylmethylzinc chlorides by direct zinc insertion into heteroarylmethyl chlorides, along with a facile and straightforward synthesis of these heterocyclic chloromethyl precursors. We demonstrate that heteroarylmethylzinc reagents undergo various reactions including cross-couplings, allylations, acylations, and addition reactions to aldehydes, leading to polyfunctional heterocyclic products. Furthermore, these heteroaromatic zinc compounds prove to be versatile reagents for the preparation of various N- and O-heterocycles and give access to an analogue of a CB1 modifier.
- Barl, Nadja M.,Sansiaume-Dagousset, Elodie,Monzon, Gabriel,Wagner, Andreas J.,Knochel, Paul
-
supporting information
p. 2422 - 2425
(2014/05/20)
-
- A remarkably faster approach towards 1,2,3-triazolyl quinolines via CuAAC in water: Their crystal structure analysis and antibacterial activities
-
A series of 1,2,3-triazolyl quinolines possessing substituents like -CH2OAr (Ar = aryl) moiety on the triazolyl ring were synthesized via a multi-step sequence consisting of copper-catalyzed azide-alkyne cycloaddition (CuAAC) of 3-(azidomethyl)
- Mareddy, Jyoti,Shanthi Praveena, Koduru Sri,Suresh, Nallapati,Jayashree, Anireddy,Roy, Soma,Rambabu, Dandela,Sreenivasa Murthy, Nandula Yadagiri,Pal, Sarbani
-
p. 343 - 352
(2013/07/26)
-
- Synthesis and structural elucidation of diversely functionalized 5,10-diaza[5]helicenes
-
Diversely functionalized diaza[5]helicenes have been synthesized starting from 6,9-dichloro-5,10-diaza[5]helicene, which was prepared from a readily available quinoline building block via Wittig reaction followed by photochemical electrocyclization. The helicene skeleton was substituted by a variety of O-, S-, N-, and C-centered nucleophiles using nucleophilic aromatic substitution reactions and palladium-catalyzed reactions like Suzuki coupling and Buchwald-Hartwig aminations. We have determined, using X-ray single-crystal diffraction, the crystal structures of the chloro- and methoxy-substituted diaza[5]helicenes. A resolution strategy based on diastereomeric separation by substitution of the dichloro derivative with a chiral amine has been shown.
- Waghray, Deepali,Zhang, Jing,Jacobs, Jeroen,Nulens, Wienand,Basaric, Nikola,Meervelt, Luc Van,Dehaen, Wim
-
p. 10176 - 10183
(2013/01/15)
-
- Design, synthesis and screening of quinoline-incorporated thiadiazole as a potential anticonvulsant
-
A series of quinoline-incorporated substituted thiadiazole were designed and synthesized using appropriate synthetic route keeping in view the structural requirement of pharmacophore and evaluated for anticonvulsant and CNS activities. After intraperitoneal injection to mice, some synthesized derivatives were examined in the maximal electroshock seizure (MES) and subcutaneous pentylenetetrazol (scPTZ)-induced seizure and neurotoxicity screens. Those found potent were also evaluated for behavioural impairment and depression activity. Among the compounds tested, 6d and 6e showed protection from seizures in both the animal models at dose level of 30mg/kg while 7f showed protection against both models at 100mg/kg dose level. These compounds exhibited lesser CNS depression and neurotoxicity compared with clinically effective drug. A series of quinoline incorporated substituted thiadiazole were designed & synthesized using appropriate synthetic route keeping in view the structural requirement of pharmacophore and evaluated for anticonvulsant and CNS activities. Among screened compounds 6d & 6e showed protection from seizures in both MES and scPTZ models at dose level (30 mg/kg).
- Kumar, Suresh,Kaushik, Darpan,Bawa, Sandhya,Khan, Suroor A.
-
experimental part
p. 104 - 111
(2012/05/04)
-
- Synthesis of New dihydropyrimidinones catalysed by dicationic ionic Liquid
-
A convenient multi step synthetic protocol for new dihydropyrimidinones bearing quinolynyl methoxy phenyl moiety has been developed from 2-chloro-3-formyl quinolines. The last step is one-pot Biginelli reaction of multicomponents, 4-((2-chloroquinolin-3-yl) methoxy) benzaldehydes, ethyl acetoacetate and urea mediated and catalysed by dicationic ionic liquid (3-methyl-1-[3-(methyl-1H-imidazolium-1-yl) propyl]- 1H-imidazolium dibromide (C3 [min]2 2 [Br-] )). Simple work-up procedures and moderate to good yields of the pyrimidinones and the intermediates are the merits of the route. Indian Academy of Sciences.
- Jawale, Dhanaji V.,Pratap, Umesh R.,Mulay, Aparna A.,Mali, Jyotirling R.,Mane, Ramrao A.
-
p. 645 - 655
(2012/07/03)
-
- TiO2 as an efficient catalytic surface for reduction of carbonyl compounds with NaBH4 under solvent-free, solid-gel and microwave irradiation
-
Structurally different carbonyl compounds such as aldehydes, ketones, α,β-unsaturated enals and enones, α-diketones and acyloins were reduced efficiently by NaBH4/TiO2 system under solvent-free, solid-gel and microwave irradiation. The chemoselective reduction of aldehydes over ketones was achieved successfully by NaBH4/TiO 2 system at solvent-free condition. In addition, regioselectivity and exclusive 1,2-reduction of Conjugated carbonyl compounds to their corresponding allylic alcohols in high to excellent yields was accomplished successfully with this reducing system.
- Setamdideh, Davood,Karimi, Zahra,Rahimi, Fatemeh
-
experimental part
p. 1621 - 1634
(2012/06/16)
-
- Synthetic Route for New (Z)-5-[4-(2-Chloroquinolin-3-yl) Methoxy]benzylidinethiazolidine-2,4-diones
-
Synthetic route has been developed for the synthesis of new (Z)-5-[4-(2-chloroquinolin-3-yl) methoxy]benzylidinethiazolidine-2,4-diones (6a-h) starting from 2-chloro-3-hydroxymethyl quinolines (2a-h). The hydroxy methyl quinolines on tosylation yielded (3a-h). Condensation of the tosyl intermediates with 4-hydroxy benzaldehydes has been carried in DMF in presence of K2CO3 and obtained 4-quinolinyl methoxy benzaldehydes (4a-h). Conveniently Knoevenagel condensation of quinolinyl methoxy benzaldehydes (4a-h) and 2, 4-thiazolidinedione (5) has been carried in PEG-400 in presence of L-proline and obtained better yields of the titled compounds (6a-h).
- Jawale, Dhanaji V.,Pratap, Umesh R.,Mane, Ramrao A.
-
experimental part
p. 2171 - 2177
(2012/06/01)
-
- Design and synthesis of 2-chloroquinoline derivatives as non-azoles antimycotic agents
-
A series of secondary amines (4-19) containing 2-chloroquinoline as lipophilic domain have been synthesizedbased on the structural requirements essential for allylamine/benzylamine antimycotics by nucleophilic substitutionreaction of 3-chloromethyl-2-chlo
- Kumar, Suresh,Bawa, Sandhya,Drabu, Sushma,Panda, Bibhu P.
-
experimental part
p. 1340 - 1348
(2012/05/05)
-
- Synthesis and antibacterial evaluation of some novel 1,3,4-oxadiazol derivatives incorporated with quinoline moiety
-
5-(3,4,5-Triethoxyphenyl)-1,3,4-oxadiazole-2-thiol 6 on treatment with substituted 3-(bromomethyl)-2-chloroquinoline or 2-(p-tolyloxy)-3-(bromomethyl) quinoline 4a-j afforded the corresponding 3-((5-(3,4,5-triethoxyphenyl)-1,3,4- oxadiazol-2-ylthio)methyl)-2-chloroquinoline or 3-((5-(3,4,5-triethoxyphenyl)-1, 3,4-oxadiazol-2-ylthio)methyl)-2-(p-tolyloxy)quinoline 7a-j, in the presence of K2CO3 and DMF under stirring at ambient temperature. All the synthesized compounds were further screened for their antibacterial activities. Some of our compounds showed excellent antibacterial activities against test organisms and reference standard.
- Mandhane, Priyanka G.,Joshi, Ratnadeep S.,Khan, Wajid,Gill, Charansingh H.
-
experimental part
p. 656 - 661
(2011/10/09)
-
- METHYL SULFANYL PYRMIDMES USEFUL AS ANTIINFLAMMATORIES, ANALGESICS, AND ANTIEPILEPTICS
-
The present invention relates to pyrimidine derivatives of Formula (Ia) and (Ib) (including tautomers, isomers, prodrugs, and pharmaceutically acceptable salts thereof). Said compounds are useful in the treatment of pain (such as neuropathic pain), inflammation, and epilepsy (by acting as anticonvulsants). Methods of medical treatment making use of said compounds, as well as additional compounds of Formula (IIa) and (IIb), are also disclosed.
- -
-
Page/Page column 117
(2010/12/18)
-
- Analysis of Cl...Cl and C-H...Cl intermolecular interactions involving chlorine in substituted 2-chloroquinoline derivatives
-
Six crystal structures of substituted 2-chloroquinoline derivatives have been analysed to evaluate the role of Cl atom as a self recognizing unit resulting in the formation of Cl...Cl and C-H...Cl interactions to generate supramolecular assembly in the solid state. The features of Type I and Type II geometries associated with Cl...Cl interactions have been analysed to show directional preferences leading to differences in the packing motifs in these crystal structures. C-H...Cl interactions are generated exclusively in structures depicting Type II Cl...Cl interaction have been observed in these structures. Indian Academy of Sciences.
- Hathwar, Venkatesha R.,Mohana Roopan,Subashini,Nawaz Khan,Guru Row
-
experimental part
p. 677 - 685
(2011/08/10)
-
- ZnO nanorods catalyzed N-alkylation of piperidin-4-one, 4(3H)-pyrimidone, and ethyl 6-chloro-1,2-dihydro-2-oxo-4-phenylquinoline-3-carboxylate
-
An efficient ligand-free cross-coupling reaction of 2-chloro-3-(chloromethyl)benzo[h]quinoline with N-heterocycles such as piperidin-4-one, 4(3H)-pyrimidone, and ethyl 6-chloro-1,2-dihydro-2-oxo-4-phenylquinoline-3-carboxylate using a catalytic amount of
- Roopan, Selvaraj Mohana,Khan, Fazlur Rahman Nawaz
-
scheme or table
p. 678 - 682
(2011/10/12)
-
- Bridged 5,6,7,8-tetrahydro-1,6-naphthyridines, analogues of huperzine A: Synthesis, modelling studies and evaluation as inhibitors of acetylcholinesterase
-
Derivatives of 6,8-bridged 5,6,7,8-tetrahydro-1,6-naphthyrid-ines, designed as analogues of huperzine A, were synthe-sised and evaluated as inhibitors of acetylcholinesterase. In a first approach, C3-bridged naphthyridines were constructed by internal nucleophilic aromatic substitution of 2-chloro-3-(1-piperidinylmethyl)pyridine precursors containing a 3-CO 2Me group on the 1-piperidinyl ring moiety. Alternatively, ring-closing metathesis on 6,8-diallyl-substituted tetrahydro-1,6-naphthyridines was applied to construct an unsaturated C4 bridge. Some of the target compounds showed inhibition of acetylcholinesterase but lower than that of huperzine A. The relative order of inhibition activities could be rationalised by comparative docking simulation studies on the basis of the known crystal structure of the ace-tylcholinesterase-huperzine A complex.
- Vanlaer, Sofie,Voet, Arnout,Gielens, Constant,De Maeyer, Marc,Compernolle, Frans
-
experimental part
p. 643 - 654
(2009/07/17)
-
- Simple and efficient synthesis of new O,O-diethyl phosphorothioates
-
A simple and highly effective method was developed for the synthesis of new O,O-diethyl phosphorothioates from O,O-diethyl phosphorochloridothioate and 2-chloroquinolin-3-ylmethanol derivatives in the presence of sodium hydroxide.
- Pokalwar,Hangarge,Kategaonkar,Shingare
-
experimental part
p. 430 - 433
(2009/09/06)
-
- Camptothecin-analog with a novel, "flipped" lactone-stable, E-ring and methods for making and using same
-
The present invention discloses: (i) a novel, lactone-stable, “flipped” E-ring camptothecin, pharmaceutically-acceptable salts, and/or analogs thereof; (ii) methods of synthesis of said novel, lactone-stable, “flipped” E-ring camptothecin, pharmaceutically-acceptable salts, and/or analogs thereof; (iii) pharmaceutically-acceptable formulations comprising said novel, lactone-stable, “flipped” E-ring camptothecin, pharmaceutically-acceptable salts, and/or analogs thereof, and, optionally, one or more additional chemotherapeutic agents; (iv) methods of administration of said novel, lactone-stable, “flipped” E-ring camptothecin, pharmaceutically-acceptable salts, and/or analogs thereof, and, optionally, one or more additional chemotherapeutic agents, to subjects in need thereof; and (v) devices for the administration of said novel, lactone-stable, “flipped” E-ring camptothecin, pharmaceutically-acceptable salts, and/or analogs thereof, and, optionally, one or more chemotherapeutic agents, to subjects in need thereof.
- -
-
Page/Page column 18; 20
(2008/12/04)
-
- Radical reactions with 3H-quinazolin-4-ones: Synthesis of deoxyvasicinone, mackinazolinone, luotonin A, rutaecarpine and tryptanthrin
-
Alkyl, aryl, heteroaryl and acyl radicals have been cyclised onto the 2-position of 3H-quinazolin-4-one. The side chains containing the radical precursors were attached to the nitrogen atom in the 3-position. The cyclisations take place by aromatic homolytic substitution hence retain the aromaticity of the 3H-quinazolin-4-one ring. The highest yields were obtained using hexamethylditin to facilitate cyclisation rather than reduction without cyclisation. The alkaloids deoxyvasicinone 2, mackinazolinone 3, tryptanthrin 4, luotonin A 5 and rutaecarpine 8 were synthesised by radical cyclisation onto 3H-quinazolin-4-one. This journal is The Royal Society of Chemistry.
- Bowman, W. Russell,Elsegood, Mark R. J.,Stein, Tobias,Weaver, George W.
-
p. 103 - 113
(2008/03/14)
-
- CAMPTOTHECIN-ANALOG WITH A NOVEL, “FLIPPED” LACTONE-STABLE, E-RING AND METHODS FOR MAKING AND USING SAME
-
The present invention discloses: (i) a novel, lactone-stable, “flipped” E-ring camptothecin, pharmaceutically-acceptable salts, and/or analogs thereof; (ii) methods of synthesis of said novel, lactone-stable, “flipped” E-ring camptothecin, pharmaceutically-acceptable salts, and/or analogs thereof; (iii) pharmaceutically-acceptable formulations comprising said novel, lactone-stable, “flipped” E-ring camptothecin, pharmaceutically-acceptable salts, and/or analogs thereof, and, optionally, one or more additional chemotherapeutic agents; (iv) methods of administration of said novel, lactone-stable, “flipped” E-ring camptothecin, pharmaceutically-acceptable salts, and/or analogs thereof, and, optionally, one or more additional chemotherapeutic agents, to subjects in need thereof; and (v) devices for the administration of said novel, lactone-stable, “flipped” E-ring camptothecin, pharmaceutically-acceptable salts, and/or analogs thereof, and, optionally, one or more chemotherapeutic agents, to subjects in need thereof.
- -
-
Page/Page column 42
(2008/06/13)
-
- Wet THF as a suitable solvent for a mild and convenient reduction of carbonyl compounds with NaBH4
-
NaBH4 in wet THF can readily reduce varieties of carbonyl compounds such as aldehydes, ketones, conjugated enones, acyloins, and α-diketones to their corresponding alcohols in good to excellent yields. Reduction reactions were performed at room temperature or under reflux condition. In addition, the chemoselective reduction of aldehydes over ketones was accomplished successfully with this reducing system.
- Zeynizadeh, Behzad,Behyar, Tarifeh
-
p. 307 - 315
(2007/10/03)
-
- Water as a green solvent for fast and efficient reduction of carbonyl compounds with NaBH4 under microwave irradiation
-
Reduction of varieties of carbonyl compounds such as aldehydes, ketones, α,β-unsaturated aldehydes and ketones, α-diketones and acyloins was carried out very fast and efficiently by sodium borohydride in water under microwave irradiation. The corresponding product alcohols were obtained in high to excellent yields.
- Zeynizadeh, Behzad,Setamdideh, Davood
-
p. 1179 - 1184
(2007/10/03)
-
- NaBH4/NaHSO4·H2O a heterogeneous acidic system for a mild and convenient reduction of carbonyl compounds under protic condition
-
NaBH4 in the presence of sodium bisulfate (NaHSO 4·H2O), a weakly acidic reagent, efficiently reduces a variety of carbonyl compounds such as aldehydes, ketones, α, β-unsaturated aldehydes and ketones, α-diketones and acyloins to their corresponding alcohols in acetonitrile under heterogeneous condition. Reduction reactions were accomplished at room temperature or under reflux condition.
- Zeynizadeh, Behzad,Behyar, Tarifen
-
p. 453 - 457
(2007/10/03)
-
- New tetracyclic analogues of camptothecins, their preparation processes, their use as medicaments and the pharmaceutical compositions containing them
-
The invention relates to new tetracyclic analogues of camptothecin, their preparation processes, their use as medicaments and the pharmaceutical compositions containing them. Said analogues, which include in particular 3-hydroxy-3-(4-oxo-4,6-dihydroindoli
- -
-
-
- Convenient one pot conversion of acetals into alcohols
-
Various acetals are conveniently converted into alcohols using a one pot procedure that combines hydrolysis of an acetal by triflouromethanesulfonic acid in tetrahydrofuran and tert-butylamine borane reduction of the resulting aldehyde.
- Lukin, Kirill A.,Yang, ChengXi,Bellettini, John R.,Narayanan,Leanna, M. Robert,Rasmussen, Michael
-
-
- Practical total synthesis of (+)-Camptothecin: The full story
-
The evolution of our strategy for the synthesis of (+)-Camptothecin and related substances is presented in detail.
- Ciufolini, Marco A.,Roschangar, Frank
-
p. 11049 - 11060
(2007/10/03)
-
- Evidence in favor of lithium-halogen exchange being faster than lithium-acidic hydrogen (deuterium) exchange
-
Treatment of 2-iodo-3-(deuterioxymethyl)quinoline with 1.5 equiv of n-butyllithium in ether, followed by aqueous work up, furnished 2-deuterio-3-(hydroxymethyl)quinoline in greater than 50% yield, confirming our earlier report,2 which has been
- Narasimhan, Nurani S.,Sunder, Nurani M.,Ammanamanchi, Radhakrishna,Bonde, Bhagavat D.
-
p. 4431 - 4435
(2007/10/02)
-