- RhIII-Catalyzed Synthesis of Highly Substituted 2-Pyridones using Fluorinated Diazomalonate
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A RhIII-catalyzed strategy was developed for the rapid construction of highly substituted 2-pyridone scaffolds using α,β-unsaturated oximes and fluorinated diazomalonate. The reaction proceeds through direct, site-selective alkylation based on migratory insertion and subsequent cyclocondensation. A wide substrate scope with different functional groups was explored. The requirement of fluorinated diazomalonate was explored for this transformation. The developed methodology was further extended with the synthesis of the bioactive compound.
- Das, Debapratim,Sahoo, Gopal,Biswas, Aniruddha,Samanta, Rajarshi
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supporting information
p. 360 - 364
(2020/01/25)
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- Novel Tetrahydroquinazolinamines as Selective Histamine 3 Receptor Antagonists for the Treatment of Obesity
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The histamine 3 receptor (H3R) is a presynaptic receptor, which modulates several neurotransmitters including histamine and various essential physiological processes, such as feeding, arousal, cognition, and pain. The H3R is considered as a drug target for the treatment of several central nervous system disorders. We have synthesized and identified a novel series of 4-aryl-6-methyl-5,6,7,8-tetrahydroquinazolinamines that act as selective H3R antagonists. Among all the synthesized compounds, in vitro and docking studies suggested that the 4-methoxy-phenyl-substituted tetrahydroquinazolinamine compound 4c has potent and selective H3R antagonist activity (IC50 0.04 μM). Compound 4c did not exhibit any activity on the hERG ion channel and pan-assay interference compounds liability. Pharmacokinetic studies showed that 4c crosses the blood brain barrier, and in vivo studies demonstrated that 4c induces anorexia and weight loss in obese, but not in lean mice. These data reveal the therapeutic potential of 4c as an anti-obesity candidate drug via antagonizing the H3R.
- Kumar, Ajeet,Pasam, Venkata Reddy,Thakur, Ravi Kumar,Singh, Maninder,Singh, Kartikey,Shukla, Mahendra,Yadav, Anubhav,Dogra, Shalini,Sona, Chandan,Umrao, Deepmala,Jaiswal, Swati,Ahmad, Hafsa,Rashid, Mamunur,Singh, Sandeep K.,Wahajuddin, Muhammad,Dwivedi, Anil Kumar,Siddiqi, Mohammad Imran,Lal, Jawahar,Tripathi, Rama Pati,Yadav, Prem N.
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p. 4638 - 4655
(2019/05/17)
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- Manganese catalyzed α-methylation of ketones with methanol as a C1 source
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The direct α-methylation of ketones with methanol under hydrogen borrowing conditions using a well-defined manganese PN3P complex as a pre-catalyst was, for the first time, achieved. The reactions typically proceed at 120 °C for 20 h with 3 mol% pre-catalyst loading and in the presence of NaOtBu (50 mol%) as base. The scope of the reaction was extended to the α-methylation of esters.
- Bruneau-Voisine, Antoine,Pallova, Lenka,Bastin, Stéphanie,César, Vincent,Sortais, Jean-Baptiste
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supporting information
p. 314 - 317
(2019/01/09)
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- Synthesis and in vitro antitumor and antimicrobial activity of some 2,3-diaryl-7-methyl-4,5,6,7-tetrahydroindazole and 3,3a,4,5,6,7-hexahydroindazole derivatives
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The synthesis of a series of 2,3-diaryl-7-methyl-4,5,6,7-tetrahydroindazole and 3,3a,4,5,6,7-hexahydroindazole derivatives substituted with various biologically-active function groups with anticipated chemotherapeutic activity is described. 4-(7-methyl-3-aryl-3,3a,4,5,6,7-hexahydro-indazol-2-yl)benzenesulfonamides 2a-c, which were employed as key intermediates in this study, were synthesized by cyclocondensation of 6-arylidene-2-methylcyclohexanones 1a-c with 4-hydrazinobenzenesulfonamide hydrochloride. A detailed discussion of the reactions utilized in the preparation of the intermediate and target compounds is reported, and the structures of the newly synthesized compounds were substantiated with IR, 1H and 13C NMR spectral data and elementary microanalyses. Twenty of the newly synthesized compounds were selected by National Cancer Institute (NCI), Maryland, USA, to be evaluated for their antitumor activity and the results revealed that six compounds 3c, 4d,e, 5a,d and 8c exhibited broad spectrum of antitumor activity against most of the tested tumor cell lines. In addition, the in vitro antibacterial and antifungal activities of a number of the target compounds were also tested using the Agar-diffusion method. Some of these compounds have shown significant antibacterial and mild to moderate antifungal activities.
- Faidallah, Hassan M.,Khan, Khalid A.,Rostom, Sherif A.F.,Asiri, Abdullah M.
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p. 495 - 508
(2015/02/19)
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- Platinum-catalyzed cyclization/[1,2]-alkyl migration/allyl shift/cyclization cascade of epoxy alkynyl allyl ethers: A step-economical route to spirobenzo[h]chromanones
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In tandem: A PtI4-catalyzed tandem reaction of epoxy alkynyl allyl ethers involving a cyclization, [1,2]-alkyl migration, O→C allyl shift, aromatic cyclization sequence has been achieved to synthesize spirobenzo[h]chromanones. The reaction simultaneously forms two adjacent stereocenters, one of which is a quaternary carbon atom (see scheme). Copyright
- Yang, Yan-Fang,Shu, Xing-Zhong,Luo, Jian-Yi,Ali, Shaukat,Liang, Yong-Min
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supporting information; scheme or table
p. 8600 - 8604
(2012/09/07)
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- Synthesis of 5-aryl-1-methyl-1,2,3,4-tetrahydrobenzo[a]phenanthridines
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5-Aryl-1-methyl-1,2,3,4-tetrahydrobenzo[a]phenanthridines were synthesized by cascade heterocyclization of the corresponding substituted benzaldehydes with 2-methylcyclohexanone and naphthalen-2-amine in a polar solvent in the presence of hydrochloric acid.
- Kozlov,Basalaeva
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experimental part
p. 587 - 590
(2009/09/06)
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- Addition of 4-Hydroxycoumarin to &α,&β-Unsaturated Carbonyl Derivatives and Mannich Base Methiodides Derived from Cyclic Ketones
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Five new 4-hydroxycoumarins incorporating a cyclic ketone have been synthesized, their structures established by PMR, IR and UV spectral data, and screened for their anticoagulant activity.
- Khanna, Vijay,Paraskar, Sunil R.,Ladwa, P. H.,Bhide, M. B.
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p. 102 - 105
(2007/10/02)
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- CATALYSE HETEROGENE PAR DES SELS ET SANS SOLVANT. III. SYNTHESE DE COMPOSES CARBONYLES α,β INSATURES A PARTIR D'ETHERS D'ENOLS SILYLES
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The reactions of silyl enol ethers with carbonyl compounds are activated by heterogeneous catalysis.Caesium fluoride is the best catalyst.Unsaturated ketones are directly obtained by condensation reactions of silyl enol ethers with aldehydes and ketones. 1,4 Addition with α,β-unsaturated carbonyl compounds gives 1,5 dicarbonyl products.This method is very convenient and the compounds obtained can easily be separated.We assume that the role of the salt in these reactions is to activate the silicon atom by anionic coordination to form a pentacoordinated silicon intermediate.
- Boyer, J.,Corriu, R. J. P.,Perz, R.,Reye, C.
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p. 157 - 166
(2007/10/02)
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