An efficient and transition metal-free method for the synthesis of aryl or alkyl difluoromethyl selenides (RSeCF2H) from the corresponding selenocyanates (RSeCN) and TMSCF2H/t-BuOK is described. The reaction performed in THF at 0 °C for 24 h or at room temperature for 6 h supplied a series of R...

6-(Difluoromethyl)indole has been characterized and developed as a probe for the turnover of indole by the bifunctional enzyme, tryptophan synthase (α2β2). The neutral form of the indolyl species undergoes a slow and spontaneous hydrolysis to produce 6-formylindole with a rate constant (k1) of...

The N-1 BOC protected precursors of 6-(fluoromethyl)indole and 6-(difluoromethyl)indole were prepared and deprotected via flash vacuum thermolysis. The stability of these newly prepared, unprotected indole derivatives has been characterized and compared to that of a previously known compound, 6-...

Here, we report the design, synthesis and structure activity relationship of novel small molecule opioid ligands based on 5-amino substituted (tetrahydronaphthalen-2-yl)methyl moiety with N-phenyl-N-(piperidin-2-yl)propionamide derivatives. We synthesized various molecules including amino, amide...

A direct chiral HPLC method has been developed and validated to quantitate the enantiomers of MDL 74 156, the primary metabolite of dolasetron mesylate, in human plasma over the concentration range 1.70–340 ng ml−1. Dolasetron mesylate is a 5-HT3 receptor antagonist that is currently being deve...

In radioligand binding experiments, MDL 73147EF and MDL 74156 inhibited the binding of [3H]GR65630 to 5-hydroxytryptamine3 (5-HT3) binding sites on membranes prepared from NG108-15 neuroblastoma × glioma cells. The calculated dissociation constants (KI) were 20.03 ± 6.58 and 0.44 ± 0.18 nM, r...

Ozonolysis of α-terpineol (1) then steam distillation in presence of acid gives the known 4-isopropylidenecyclopentenyl methyl ketone (4). This is oxidized in air to 4-(1-hydroperoxy-1-methylethyl)-1,3-cydopentadienyl methyl ketone (10), a compound frequently reacting as if it were one of the e...

3-(1-Methylethyl)-7-methyl2,6-octadienal, was prepared from 1,1,3-triethoxy-3,4-dimethylpentane and 3-methyl-2-buten-l-ol in a one-pot procedure utilising Claisen and Cope rearrangement of an intermediate dienol-allyl ether.

Neodymium trichloride reacts with 2 equiv. of the lithium salt of 9-(cyclopentadienyl-1-methylethyl)-9,10-dihydroanthracene in THF to give the “ate” complex [Li(THF)4][Nd{(C5H4)CMe2 (C14H10)}2] which has been characterized by its crystal structure and elemental analysis. The neodymium atom is ...

A non-methionine FT inhibitor lead structure (1) was designed through computer modeling of the peptidomimetic FT inhibitor ABT839. Optimization of this lead resulted in compounds 2e and 2g, with FT IC50 values of 1.3 and 1.8 nM, GGT IC50 of 1400 nM, and EC50 (Ras processing) values of 13 and 11 ...

The synthetic utility of 2-mercaptonicotinonitriles 3 and 4, as well as 2-mercapto-4-oxo-6-phenyl-1,4-dihydropyrimidine-5-carbonitrile 20 as building blocks for novel bis- and poly(pyridines), along with poly(pyrimidines) via alkylation with the corresponding bis- and poy(halo) compounds was inv...

Results of the detailed investigations on the bromination of the methyl group of 3-aryl-5-methyl-isoxazole-4-carboxylate, a precursor to obtain 3-aryl-5-formyl-isoxazole-4-carboxylate, are described. The products generated during the study have been utilized as substrates for the synthesis of is...

The 3,4-bis(bromomethyl) methoxybenzene addition product of [6,6]-phenyl-C61-butyric acid methyl ester (PCBM), namely, 2-methoxy-(5,8)-dihydronaphthyl-PCBM (MDN-PCBM), was designed, synthesized, and evaluated for its photovoltaic performance in polymer solar cells (PSCs). The energy level of the...

The ethyl α-bromomethyl-β-(diethoxyphosphoryl)acrylic acid ester 9 has been prepared by addition of bromine to allylphosphonate 7 then dehydrobromination with DBU in acetonitrile. Reaction of allylic bromide 9 with primary amines in a bimolecular SN2′-type mecanism in methanol at low temperat...

2-Bromomethyl-3-aryl-2-propenoic acids have been synthesized from Baylis–Hillman adducts derived from aromatic aldehydes and t-butyl acrylates as new precursors in MBH chemistry. Further triolides were synthesized by the cyclo-oligomerization of 2-bromomethyl-3-aryl-2-propenoic acids in the pre...

(S)-4-Methyl-3,6-dihydro-2H-pyran-2-carbaldehyde (3), the common intermediate in the syntheses of the C17–C27 subunit of laulimalide (4) and (+)-faranal (5), the trail pheromone of the pharaoh ant, Monomorium pharaonis, were obtained via transformation of methyl 3-bromomethyl-3-butenoate (1) in...

A short synthesis of alkyl 2-(bromomethyl)aziridine-2-carboxylates and alkyl 3-bromoazetidine-3-carboxylates was developed involving amination, bromination, and base-induced cyclization of alkyl 2-(bromomethyl)acrylates. These new small ring azaheterocyclic α- and β-amino acid derivatives are ...

An unexpected, but simple method for the efficient synthesis of new 2.2′-azopyridine dyes, such as (E)-diethyl 6,6′-(diazene-1,2-diyl)bis(5-cyano-2-methyl-4-phenylnicotinates) (2, 4, 6, 8, 10, and 12), based on the treatment of ethyl 6-amino-5-cyano-2-methyl-4-arylnicotinates (1, 3, 5, 7, 9, a...

Our prior work demonstrated the involvement of the caudal granular subregion of the insular cortex in a rat model of nicotine self-administration. Recent studies in various animal models of addiction for nicotine and other drugs have identified a role for the rostral agranular subregion (RAIC). ...

Adolescent cigarette use is associated with reduced quitting success and continued smoking in adulthood. Interestingly, polymorphisms of the dopamine D3 receptor (DRD3) gene have been associated with smoking behavior, and the receptor is expressed in an age- and brain region-dependent manner tha...