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2.
Org Lett ; 22(1): 239-243, 2020 01 03.
Article in English | MEDLINE | ID: mdl-31845813

ABSTRACT

A simple, inexpensive, step economic, and highly modular synthetic strategy to access izidine alkaloids is described. The key step is a TfOH-promoted intramolecular aldol condensation between enol and cyclic imide moieties. This cyclization strategy can be employed within an aza-Robinson annulation framework and represents a general tool to build fused bicyclic amines. To illustrate the power of this method, we describe the preparation of (±)-coniceine, (±)-quinolizidine, (±)-tashiromine, (±)-epilupinine, and the core of (±)-valmerins.

3.
Org Lett ; 21(17): 6909-6913, 2019 09 06.
Article in English | MEDLINE | ID: mdl-31433655

ABSTRACT

A thermal protocol is reported for the formal insertion of nitric acid into aryldiazoacetates using Fe(NO3)3·9H2O. This strategy is mild and high yielding and allows the preparation of a large variety of members of an unprecedented family of organic nitrates. The nitrate group can be also readily transformed into other functional groups and heterocyclic moieties and can possibly allow new biological explorations of untapped potential associated with their NO-releasing ability.

4.
Vector Borne Zoonotic Dis ; 18(10): 548-553, 2018 10.
Article in English | MEDLINE | ID: mdl-29969388

ABSTRACT

An organic salt and four metal complexes derived from azole were evaluated against embryonated Toxocara canis eggs (TCE). The new organic salt, (LH)+(FeCl4)-, where L = 3,5-bis(3,5-dimethylpyrazole-1-ylmethyl)toluene (5), a potential environmental disinfectant, was isolated as an air-stable yellow solid and characterized by elemental analysis, electrical conductivity, mass spectrometry, and infrared and ultraviolet/visible spectroscopy. In addition, the structure of 5 was determined by single-crystal X-ray diffraction. Compound 2 showed high anti-TCE activity. Interestingly, these compounds showed little effect on hepatocytes, indicating that they are not cytotoxic. These results will assist in the design of anti-TCE compounds.


Subject(s)
Anthelmintics/pharmacology , Azoles/pharmacology , Coordination Complexes/pharmacology , Ovum/drug effects , Toxocara canis/drug effects , Animals , Anthelmintics/chemical synthesis , Anthelmintics/chemistry , Azoles/chemical synthesis , Azoles/chemistry , Coordination Complexes/chemical synthesis , Coordination Complexes/chemistry , Models, Molecular , Molecular Structure
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