- Lewis acid-promoted synthesis of highly substituted pyrrole-fused benzoxazinones and quinoxalinones
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A synthesis of a series of novel fused tricyclic heterocyclic compounds has been achieved in one-pot reaction set up starting from (E)-3-(2-oxo-2-phenylethylidene)indolin-2-one and 1,4-benzoxazinone/quinoxalinone derivatives promoted by tin(IV) chloride.
- Selvendran, Suresh,Rajendran, Saravanakumar
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supporting information
p. 437 - 445
(2020/10/22)
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- Novel N-benzylpiperidine derivatives of 5-arylisoxazole-3-carboxamides as anti-Alzheimer's agents
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The complex pathophysiology of Alzheimer's disease (AD) has prompted researchers to develop multitarget-directed molecules to find an effective therapy against the disease. In this context, a novel series of N-(1-benzylpiperidin-4-yl)-5-arylisoxazole-3-ca
- Saeedi, Mina,Felegari, Peyman,Iraji, Aida,Hariri, Roshanak,Rastegari, Arezoo,Mirfazli, S. Sara,Edraki, Najmeh,Firuzi, Omidreza,Mahdavi, Mohammad,Akbarzadeh, Tahmineh
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- Design and synthesis of novel 5-arylisoxazole-1,3,4-thiadiazole hybrids as α-glucosidase inhibitors
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Background: α-Glucosidase inhibitors have occupied a significant position in the treatment of type 2 diabetes. In this respect, the development of novel and efficient non-sugar-based inhibitors is in high demand. Objective: Design and synthesis of new 5-arylisoxazole-1,3,4-thiadiazole hybrids possessing α-glucosidase inhibitory activity were developed. Methods: Different derivatives were synthesized by the reaction of various 5-arylisoxazole-3-carboxylic acids and ethyl 2-((5-amino-1,3,4-thiadiazol-2-yl)thio)acetate. Finally, they were evalu-ated for their α-glucosidase inhibitory activity. Results: It was found that ethyl 2-((5-(5-(2-chlorophenyl)isoxazole-3-carboxamido)-1,3,4-thiadiazol-2-yl)thio)acetate (5j) was the most potent compound (IC50 = 180.1 μM) compared with acarbose as the reference drug (IC50 = 750.0 μM). Also, the kinetic study of 5j revealed a competitive inhibition and docking study results indicated desired interactions of that compound with amino acid residues located close to the active site of α-glucosidase. Conclusion: Good α-glucosidase inhibitory activity obtained by the title compounds introduced them as an efficient scaffold, which merits to be considered in anti-diabetic drug discovery developments.
- Akbarzadeh, Tahmineh,Eslami, Azadeh,Faramarzi, Mohammad Ali,Mahdavi, Mohammad,Mirfazli, Seyedeh Sara,Saeedi, Mina,Zardkanlou, Mahsa
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p. 436 - 444
(2021/10/04)
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- Ruthenium-Catalyzed Asymmetric Transfer Hydrogenation of β-Substituted α-Oxobutyrolactones
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A concise and effective ruthenium-catalyzed asymmetric transfer hydrogenation of β-substituted α-oxobutyrolactones has been developed, delivering a series of cis-β-substituted α-hydroxybutyrolactone derivatives with excellent yields, enantioselectivities,
- Hu, Zi-Qi,Li, Xiang,Liu, Li-Xia,Yu, Chang-Bin,Zhou, Yong-Gui
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supporting information
p. 17453 - 17461
(2021/11/18)
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- Design and Synthesis of Novel Arylisoxazole-Chromenone Carboxamides: Investigation of Biological Activities Associated with Alzheimer's Disease
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A novel series of hybrid arylisoxazole-chromenone carboxamides were designed, synthesized, and evaluated for their cholinesterase (ChE) inhibitory activity based on the modified Ellman's method. Among synthesized compounds, 5-(3-nitrophenyl)-N-{4-[(2-oxo-
- Akbarzadeh, Tahmineh,Edraki, Najmeh,Firuzi, Omidreza,Hariri, Roshanak,Mahdavi, Mohammad,Mirfazli, Seyedeh Sara,Rastegari, Arezoo,Saeedi, Mina
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- Green and efficient synthesis of new pyrido[2,3-d]pyrimidine derivatives using Pd/SBA-15 as a nanocatalyst
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N-Fused heterocycles have received significant attention over the years as valuable compounds due to their biological and pharmaceutical activities. Heterogeneous catalysts such as periodic mesoporous materials have played an important role in the synthes
- Bardajee, Ghasem Rezanejade,Delbari, Akram Sadat,Ghaedi, Aseyeh,Hekmat, Shohreh
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- Synthesis, biological evaluation and in silico modelling studies of 1,3,5-trisubstituted pyrazoles carrying benzenesulfonamide as potential anticancer agents and selective cancer-associated hCA IX isoenzyme inhibitors
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Inhibition of carbonic anhydrases (CAs, EC 4.2.1.1) has clinical importance for the treatment of several diseases. They participate in crucial regulatory mechanisms for balancing intracellular and extracellular pH of the cells. Among CA isoforms, selectiv
- Yamali, Cem,Gul, Halise Inci,Ece, Abdulilah,Bua, Silvia,Angeli, Andrea,Sakagami, Hiroshi,Sahin, Ertan,Supuran, Claudiu T.
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- Synthetic method of OLED material intermediate benzoyl pyrimidine compound
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The invention discloses a synthetic method of an OLED material intermediate benzoyl pyrimidine compound. The synthetic method comprises the following steps: mixing alkali, a solvent I as well as substituent acetophenone and oxalic acid diester which are u
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Paragraph 0144; 0145; 0150; 0151; 0156; 0157; 0162; 0163
(2018/07/15)
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- The First Example of Azole-Fused Cyclic Anhydride Reacting in the Castagnoli-Cushman Way
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Pyrazole-fused cyclic anhydrides have been employed for the first time as the Castagnoli-Cushman reaction partners to produce hitherto unknown 4-oxo-4,5,6,7-tetrahydropyrazolo[1,5- a ]pyrazine-7-carboxylates in remarkably convenient and speedy fashion. At
- Moreau, Ella,Dar'In, Dmitry,Krasavin, Mikhail
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supporting information
p. 890 - 893
(2018/03/06)
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- Design, synthesis and structure-based optimization of novel isoxazole-containing benzamide derivatives as FtsZ modulators
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Antibiotic resistance among clinically significant bacterial pathogens is becoming a prevalent threat to public health, and new antibacterial agents with novel mechanisms of action hence are in an urgent need. Utilizing computational docking method and structure-based optimization strategy, we rationally designed and synthesized two series of isoxazol-3-yl- and isoxazol-5-yl-containing benzamide derivatives that targeted the bacterial cell division protein FtsZ. Evaluation of their activity against a panel of Gram-positive and -negative pathogens revealed that compounds B14 and B16 that possessed the isoxazol-5-yl group showed strong antibacterial activity against various testing strains, including methicillin-resistant Staphylococcus aureus and penicillin-resistant S. aureus. Further molecular biological studies and docking analyses proved that the compound functioned as an effective inhibitor to alter the dynamics of FtsZ self-polymerization via a stimulatory mechanism, which finally terminated the cell division and caused cell death. Taken together, these results could suggest a promising chemotype for development of new FtsZ-targeting bactericidal agent.
- Bi, Fangchao,Song, Di,Zhang, Nan,Liu, Zhiyang,Gu, Xinjie,Hu, Chaoyu,Cai, Xiaokang,Venter, Henrietta,Ma, Shutao
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- Synthesis and cellular bioactivities of novel isoxazole derivatives incorporating an arylpiperazine moiety as anticancer agents
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In our endeavour towards the development of effective anticancer therapeutics, a novel series of isoxazole-piperazine hybrids were synthesized and evaluated for their cytotoxic activities against human liver (Huh7 and Mahlavu) and breast (MCF-7) cancer ce
- ?al??kan, Burcu,?bi?, Kübra,Banoglu, Erden,Sinoplu, Esra,Akhan Güzelcan, Ece,?etin Atalay, Rengül
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p. 1352 - 1361
(2018/11/21)
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- 1. 3, 5 - tri-substituted pyrazole compound and its preparation method and application
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The invention discloses 1,3,5-trisubstituted pyrazole compounds, and a preparation method and application thereof. The structure of the compounds is shown as a general formula (I), and in the general formula (I), R1 is hydrogen, halogens, methyl or triflu
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Paragraph 0103; 0106; 0107; 0108; 0109; 0112
(2017/04/18)
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- Simple and efficient syntheses of novel benzo[4,5]imidazo[1,2-a]pyridine derivatives
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A novel series of benzo[4,5]imidazo[1,2-a]pyridine derivatives is synthesized through the reaction of 2-(1H-benzo[d]imidazol-2-yl)acetonitrile and different ethyl 2,4-dioxo-4-arylbutanoate derivatives in the presence of piperidine in refluxing EtOH. All the products are easily prepared within 25-45 min in good to excellent yields.
- Goli-Garmroodi, Fereshteh,Omidi, Marzieh,Saeedi, Mina,Sarrafzadeh, Farhad,Rafinejad, Ali,Mahdavi, Mohammad,Bardajee, Ghasem Rezanejade,Akbarzadeh, Tahmineh,Firoozpour, Loghman,Shafiee, Abbas,Foroumadi, Alireza
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p. 743 - 746
(2015/01/30)
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- Diphenylpyrazoles as replication protein A inhibitors
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Replication Protein A is the primary eukaryotic ssDNA binding protein that has a central role in initiating the cellular response to DNA damage. RPA recruits multiple proteins to sites of DNA damage via the N-terminal domain of the 70 kDa subunit (RPA70N). Here we describe the optimization of a diphenylpyrazole carboxylic acid series of inhibitors of these RPA-protein interactions. We evaluated substituents on the aromatic rings as well as the type and geometry of the linkers used to combine fragments, ultimately leading to submicromolar inhibitors of RPA70N protein-protein interactions.
- Waterson, Alex G.,Kennedy, J. Phillip,Patrone, James D.,Pelz, Nicholas F.,Feldkamp, Michael D.,Frank, Andreas O.,Vangamudi, Bhavatarini,Souza-Fagundes, Elaine M.,Rossanese, Olivia W.,Chazin, Walter J.,Fesik, Stephen W.
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supporting information
p. 140 - 145
(2015/03/04)
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- Facile, novel and efficient synthesis of new pyrazolo[3,4-b]pyridine products from condensation of pyrazole-5-amine derivatives and activated carbonyl groups
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An efficient synthesis of novel ethyl-1,3,4-triphenyl-1H-pyrazolo[3,4-b]pyridine-6-carboxylate products has been achieved via condensation of pyrazole-5-amine derivatives and activated carbonyl groups, in refluxing acetic acid. This process has been found to be useful in the preparation of new N-fused heterocycle products in good to excellent yields.
- Ghaedi,Bardajee,Mirshokrayi,Mahdavi,Shafiee,Akbarzadeh
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p. 89652 - 89658
(2015/11/10)
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- Concise synthesis of α-(hydroxymethyl) alkyl and aryl vinyl ketones
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2,4-Diketoesters 2 have first been reported as starting materials for the synthesis of a new class of α-hydroxymethyl-α,β-unsaturated ketones 3. Thus, under heterogeneous liquid-liquid medium in the presence of concentrated aqueous potassium carbonate as a base, both aliphatic and aromatic 2,4-dioxoalkanoates 2 react with aqueous formaldehyde to afford the corresponding ketones 3 in fair to good yields. Copyright Taylor & Francis Group, LLC.
- Kraem, Jihene Ben,Amri, Hassen
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p. 110 - 117
(2012/10/30)
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- Synthesis and anti-inflammatory activity of some novel 3-phenyl-N-[3-(4- phenylpiperazin-1yl)propyl]-1H-pyrazole-5-carboxamide derivatives
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A new series of 3-phenyl-N-[3-(4-phenylpiperazin-1yl)propyl]-1H-pyrazole-5- carboxamide derivatives were synthesized and investigated their anti-inflammatory activities using carrageenan-induced rat paw edema model in vivo. All the synthesized compounds were found to be potent anti-inflammatory agents.
- Nagarapu, Lingaiah,Mateti, Jhansi,Gaikwad, Hanmant K.,Bantu, Rajashaker,Sheeba Rani,Prameela Subhashini
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scheme or table
p. 4138 - 4140
(2011/08/06)
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- Design and synthesis of novel pyrazole-based Lp-PLA2 inhibitors
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A series of novel pyrazole-based lipoprotein-associated phospholipase A2 (Lp-PLA2) inhibitors have been designed and synthetized by a variety of acetophenones via a 10-step convergent approach. The synthetic approach is carefully opt
- Wang, Yi,Xu, Weiren,Shao, Hua,Xie, Yafei,Wang, Jianwu
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experimental part
p. 2039 - 2048
(2012/03/26)
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- Synthesis and cytotoxicity evaluation of 1-[3-(9H-carbazol-4-yloxy)-2- hydroxypropyl]-3-aryl-1H-pyrazole-5-carboxylic acid derivatives
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Several novel molecules, 1-(3′-(9H-carbazol-4-yloxy)-2′- hydroxypropyl)-3-aryl-1H-pyrazole-5-carboxylic acid derivatives 3a-g were synthesized and screened to evaluate their cytotoxicity against cancer cells in vitro. The compounds 3a-g has been prepared by the reaction of ethyl 3-aryl-1H-pyrazole-5-carboxylate with 4-oxiranylmethoxy-9H-carbazole in moderate to excellent yields. The cytotoxicity of synthesized compounds was evaluated by a SRB (sulforhodamine B) assay against cancer cell such as SK-N-SH human neuroblastoma (NB), human A549 lung carcinoma, human breast cancer MCF-7 cell lines. The results showed that seven compounds can suppress SK-N-SH tumor cancer cell growth. Among them, compound 3d was the most effective small molecule in inhibiting SK-N-SH cell growth.
- Nagarapu, Lingaiah,Gaikwad, Hanmant K.,Sarikonda, Kartheeka,Mateti, Jhansi,Bantu, Rajashaker,Raghu,Manda, Krishna Madhuri,Kalvendi, Shasi Vardhan
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experimental part
p. 4720 - 4725
(2010/11/16)
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- Regioselective synthesis of 4-acyl-1-hydroxy-2,3-benzodioates by chelation-controlled [3+3] annulation of 3-acyl-4-ethoxy-2-oxo-3-enoates with 1,3-bis(trimethylsilyloxy)-1,3-butadienes
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4-Acyl-1-hydroxy-2,3-benzodioates were regioselectively prepared by chelation-controlled [3+3] cyclization of 1,3-bis(trimethylsilyloxy)-1,3- butadienes with 3-acyl-4-ethoxy-2-oxo-3-enoates.
- Riahi, Abdolmajid,Shkoor, Mohanad,Fatunsin, Olumide,Khera, Rasheed Ahmad,Fischer, Christine,Langer, Peter
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supporting information; experimental part
p. 4248 - 4251
(2009/12/06)
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- Discovery of α,γ-Diketo Acids as Potent Selective and Reversible Inhibitors of Hepatitis C Virus NS5b RNA-Dependent RNA Polymerase
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α,γ-Diketo acids (DKA) were discovered from screening as selective and reversible inhibitors of hepatitis C virus NS5b RNA-dependent RNA polymerase. The diketo acid moiety proved essential for activity, while substitution on the γ position was necessary for selectivity and potency. Optimization led to the identification of a DKA inhibitor of NS5b polymerase with IC50 = 45 nM, one of the most potent HCV NS5b polymerase inhibitors reported.
- Summa, Vincenzo,Petrocchi, Alessia,Pace, Paola,Matassa, Victor G.,De Francesco, Raffaele,Altamura, Sergio,Tomei, Licia,Koch, Uwe,Neuner, Philippe
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- Facile Baylis-Hillman Reaction of Substituted 3-Isoxazolecarbaldehydes: The Impact of a Proximal Heteroatom Within a Heterocycle on the Acceleration of the Reaction
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The fast and facile Baylis-Hillman reaction in substituted 3-isoxazolecarbaldehydes confirms the impact of the proximal heteroatom within a heterocycle towards enhanced reactivity of the formyl group for this reaction.
- Roy, Amrendra K.,Batra, Sanjay
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p. 2325 - 2330
(2007/10/03)
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