N-Trimethylsilyloxy-N-benzyl-1-alkyl-2-acetoxy-3-buten-1-amines 13, obtained in good yields and moderate diastereoselectivities by TMSOTf promoted α-acetoxyallylation of nitrones using metallic zinc and 3-bromo-propenyl acetate 11, are exploited in a stereospecific 5-exo-trig iodocyclization re...

C-Substituted iodinated analogues of d-glucose have been prepared from diacetone-d-glucose or d-glucuronic acid derivatives; in these compounds, each hydroxyl group of glucose is present.

Palladium/CuI catalyzed reactions of 2-iodo-3-iodomethyl-1,4-diarylnaphthalenes in the presence of arylacetylenes produced the corresponding sp3–sp3 homo-coupling products 1,2-bis(3-iodonaphthalen-2-yl)ethane in moderate to good yields.

1-Azabicyclo[1.1.0]butane 2 was successfully synthesized by treatment of 2,3-dibromopropylamine hydrobromide 4 with organolithium compounds and was readily converted to 1-(1,3-thiazolin-2-yl)azetidine-3-thiol hydrochloride 1 and versatile azetidine derivatives 9 and 10.

Electrophilic additions of arenesulfonyl azides (i.e., TsN3 and NsN3) to 3-ethyl-1-azabicyclo[1.1.0]butane (1) in CDCl3 at 80°C has been observed to result in the formation of oligomeric products. The mechanism of these reactions probably involves the formation of a carbocationic intermediate, ...

The ring-opening reactions of 1-azabicyclo[1.1.0]butane 3 with thiols 6a–f gave 3-sulfenylazetidine derivatives 7a–f in 50-92% yields. Treatment of 3 with aromatic amines 11a–e and dibenzylamine 11f in the presence of Mg(ClO4)2 afforded the corresponding 3-aminoazetidine derivatives 12a–f in...

A set of 18 new C4 and C1 derivatives of nor-cerpegin (1,1-dimethyl furo[3,4-c]pyridine-3-one), 6 model compounds (γ- and δ-lactones) and 20 furo- or thieno[2,3-d]-pyrimidine-4-one related compounds were designed and synthesized. Each compound was assayed for inhibition of CT-L, T-L and PA pro...

A novel α7 nAChR agonist, N-[(3R,5R)-1-azabicyclo[3.2.1]oct-3-yl]furo[2,3-c]pyridine-5-carboxamide (3a, PHA-709829), has been identified for the potential treatment of cognitive deficits in schizophrenia. The compound shows potent and selective α7 in vitro activity, excellent brain penetration...

A series of novel trifluoromethyl substituted furo[2,3-b]pyridine and pyrido[3′,2′:4,5]furo[3,2-d] pyrimidine derivatives 3a-b, 6a-k, 9, 10a-b, 11a-c and 12a-c were prepared from 2-carbethoxy-3-amino-6-trifluoromethyl furo[2,3-b]pyridine 1 under different set of conditions. Compounds functiona...

2-Furfuraldoxime is used for the first time as a heterodiene in Diels-Alder reactions. Synthesis of 5 substituted and 4,5-disubstituted furo [2,3-c] pyridine N oxides based on this method is reported.

Forty seven thieno[2,3-b]pyridines-2-carboxamides, furo[2,3-b]pyridines-2-carboxamides and tetrahydrothieno[2,3-b]quinolones-2-carboxamides derivatives were synthesized and tested for their antiproliferative activity against the NCI-60 cell lines. The 5-keto-tetrahydrothieno[2,3-b]quinolones-2-c...

Serotoninergic neurotransmission has been implicated in modulation of learning and memory. It has been demonstrated that 5-hydroxytryptamine6 (5-HT6) receptor antagonists show beneficial effect on cognition in several animal models. Based on a pharmacophore model reported in the literature, we h...

Identification of new antibiotics suitable for the treatment of tuberculosis is required. In addition to selectivity, it is necessary to find new antibiotics that are effective when the tuberculous mycobacteria are resistant to the available therapies. The furo[2,3-b]pyridine core offers potenti...

Virtual and high-throughput screening identified imidazo[1,2-a]pyrazines as inhibitors of B-Raf. We describe the rationale, SAR, and evolution of the initial hits to a series of furo[2,3-c]pyridine indanone oximes as highly potent and selective inhibitors of B-Raf.

Three 3β-(β,β-dimethylaminoethoxy)-substituted steroids, DAEA, DAEAM, and DAEC, have been found to be potent blockers of the enzyme system participating the conversion of β-sitosterol into cholesterol in the silkworm larvae. Thus, a preliminary site of inhibitory action of these steroids is ...

The injection of β-ecdysone into chilled Hyalophora gloveri pupae resulted in the stimulation of adenyl cyclase activity in the wing epidermis as measured by the incorporation of label into cyclic AMP from a prelabeled endogenous pool. Stimulation was also obtained in pupal wings in vitro and i...

Scintillation counting and radioautographic methods were used to study the incorporation of a chitin precursor, d-glucosamine-6-3H, into wing disks in vitro. Both alpha-ecdysone and beta-ecdysone stimulated uptake of the isotope by the disks, but only beta-ecdysone caused marked localization of ...

Ecdysteroids exert many pharmacological effects in mammals (including humans), most of which appear beneficial, but their mechanism of action is far from understood. Whether they act directly and/or after the formation of metabolites is still an open question. The need to investigate this questi...

Structural modification of 20-hydroxyecdysone (20E) based on photochemical transformation yielded dimeric ecdysteroid 7αH,7′αH-bis-[(20R,22R)-2β,3β,20,22,25-pentahydroxy-5β-cholest-8(14)-en-6-one-7-yl] as a main product. Its structure was determined by detailed NMR analysis. Furthermore, t...

A principal unidentified compound in the free ecdysteroid fraction and its conjugated form were purified from c.3 kg of ovaries of the silkworm, Bombyx mori, mainly by means of thin-layer chromatography and high-performance liquid chromatography. The purified compounds were identified as 22-deox...