Six-membered Rings with More than One Oxygen or Sulfur Atom

Cook, Michael J.

doi:10.1016/b978-008096519-2.00048-5

Cited by 9 publications

(5 citation statements)

References 310 publications

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“…The formation of 7 can be explained by the presence ofNazSa in the NazS reagent, since Na2Sz has been used to convert 1,4-dibromobutanes to 1,2-dithianes. 13 Compounds 6 and 7 were fully characterized by mass spectral, NMR, and elemental analyses (see Table III).…”

Section: Introductionmentioning

confidence: 99%

Structure-based design of inhibitors of purine nucleoside phosphorylase. 2. 9-Alicyclic and 9-heteroalicyclic derivatives of 9-deazaguanine

Secrist

Niwas²,

Rose³

et al. 1993

J. Med. Chem.

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Section: Introductionmentioning

confidence: 99%

Structure-based design of inhibitors of purine nucleoside phosphorylase. 2. 9-Alicyclic and 9-heteroalicyclic derivatives of 9-deazaguanine

Secrist

Niwas²,

Rose³

et al. 1993

J. Med. Chem.

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“…In the present work besides these two routes, we present new reactions of cyclofunctionalizations type phenoxazinic (IV), indolidinic (V), pyranic (VII) and cyclopentenic (VI/VIII) (Scheme 2), following the patterns IV−VIII, all leading to compounds 18−27, which, as to our knowledge, are described here for the first time. The formation of phenoxazinic rings from phenols is already known in the literature [40], however the synthesis of compound 18, originated from 1, represents the novelty of the ring being formulated from a hydroxy naphthoquinoidal structure. Thus, the utilization of the quinoidal system transformed in heterocyclic compounds extends the interest for the chemistry of natural products to the interface chemistry/biological screening in the area of tropical diseases.…”

Section: Resultsmentioning

confidence: 99%

Chemical Reactivity Studies with Naphthoquinones from Tabebuia with Anti-trypanosomal Efficacy

Pinto

Dantas

Moura

et al. 2011

Arzneimittelforschung

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The biological activities of the naphthoquinones lapachol and its cyclization product beta-lapachone, extracted from trees of the genus Tabebuia, have been intensively studied. Given continuity to the studies about heterocyclic derivatives obtained from the reaction of these naphtoquinones with amino-containing reagents, 22 derivatives of beta-lapachone, nor-beta-lapachone and lapachol were synthesised and their activities against trypomastigote forms of T. cruzi were evaluated. The compounds were grouped as oxazolic, imidazolic, phenoxazinic, indolic, pyranic and cyclopentenic derivatives. The variability of the new structures is based on the great electrophilicity of 1,2-quinoidal carbonyls towards reagents containing nitrogen or carbon as nucleophilic centres. In relation to the trypanocidal activity of the synthesised compounds, in view of their structural diversity, tendencies only could be verified. Among the cyclofunctionalised products the oxazolic and imidazolic derivatives showed +/- 1.5 to 34.8 times higher activity than crystal violet, the standard drug for the sterilization of stored blood. These results corroborate the tendency of trypanocidal activity in imidazolic skeletons, and indicate that this moiety could be used as a guide for architectural delineation of molecules with potential value for the chemotherapy of Chagas disease.

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“…The difference in size, electronegativity, and bond polarities as- sociated with oxygen and sulfur, as well as the availability of 3d orbitals in sulfur is reflected in contrasting structural [11], conformational [12,13], and reactivity behavior [14] of the corresponding hetero cycles. Thus, C-O-C bond angles are substantially larger (ca.…”

Section: Oxygen-and Sulfur-containing Six-membered Ringsmentioning

confidence: 99%

Thermochemistry of organic molecules: The way to understand energy–structure relationships

Roux

Foces‐Foces

Notario

2009

Pure and Applied Chemistry

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The combination of experimental calorimetric measurements, particularly of the standard energies and enthalpies of combustion and formation, and theoretical examination of model molecules constitutes a powerful tool for the understanding of the conformational and chemical behavior of organic molecules.In this article, several examples are provided where the synergy between experiment and theory made possible the comprehension of various fundamental interactions in oxygenand sulfur-containing six-membered heterocyclic compounds, the determination of the strain energy in two C 8 H 8 derivatives, dimethyl cubane-1,4-dicarboxylate and dimethyl cuneane-2,6-dicarboxylate, and the calculation of the enthalpies of formation of the parent compounds, cubane and cuneane, and the study of the energy-structure relationship in barbituric acid.that are responsible for the enthalpy of formation of each isomer. As an example, we can consider the enthalpies of formation of the three isomers of formula C 5 H 12 , pentane, 2-methylbutane, and 2,2-dimethylpropane determined and published by Good [1] and given in Table 1.

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Six-membered Rings with More than One Oxygen or Sulfur Atom

Cited by 9 publications

References 310 publications

Structure-based design of inhibitors of purine nucleoside phosphorylase. 2. 9-Alicyclic and 9-heteroalicyclic derivatives of 9-deazaguanine

Structure-based design of inhibitors of purine nucleoside phosphorylase. 2. 9-Alicyclic and 9-heteroalicyclic derivatives of 9-deazaguanine

Chemical Reactivity Studies with Naphthoquinones from Tabebuia with Anti-trypanosomal Efficacy

Thermochemistry of organic molecules: The way to understand energy–structure relationships

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