Crystallographic studies on retinoidal-active and -inactive aromatic anilides

Toriumi, Yoshiharu; Kasuya, Atsushi; Itai, Akiko

doi:10.1021/jo00288a043

Cited by 22 publications

(12 citation statements)

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“…This is consistent with the lack of quenching observed in the Cu 2+ -L 2 mixture. Dihedral angles of amide bonds may influence internal charge transfer [38][39], but in our case we find that such differences are not important in this set of compounds because the optimized geometry of the isomers do not show significant differences.…”

Section: Figure 3 Herecontrasting

confidence: 49%

Distinctions of positional isomers of N-(methylthiazol-2-yl)nitrobenzamide by copper and iron ions

Phukan

Goswami

Baruah

2015

Inorganica Chimica Acta

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Section: Figure 3 Herecontrasting

confidence: 49%

Distinctions of positional isomers of N-(methylthiazol-2-yl)nitrobenzamide by copper and iron ions

Phukan

Goswami

Baruah

2015

Inorganica Chimica Acta

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“…To the least of our knowledge, there has been no report in literature that the amide proton of benzanilide plays an important role as H-bonding donor with the receptor. Itai et al, reported that the N -methylbenzanilide took a folded cis conformation, whereas, the free amide molecule took an extended trans conformation. We obtained similar results in a modeling study of compounds 31b and 31s .…”

Section: Referencesmentioning

confidence: 99%

Orally Active, Nonpeptide Vasopressin V₂ Receptor Antagonists: A Novel Series of 1-[4-(Benzoylamino)benzoyl]-2,3,4,5-tetrahydro-1H-benzazepines and Related Compounds

et al. 1996

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This paper describes a novel series of nonpeptide vasopressin V2 receptor antagonists. It has been demonstrated that the 1-[4-(benzoylamino)benzoyl]-2,3,4,5-1H-benzazepines and 1-[4-(benzoylamino)benzoyl]-2,3,4,5-1H-1,5-benzodiazepines show a high affinity for V2 (and V1a) receptors. Among the 1-[4-(benzoylamino)benzoyl]-2,3,4,5-1H-benzazepine series, compounds with an alkylamino group on the benzazepine ring have been shown to have oral activity. A lipophilic group at the ortho position on the terminal benzoyl ring is important for both high V2 receptor affinity and oral activity. On the basis of these favorable properties, clinical testing of 31b has begun for use as an oral and iv aquaretic agent.

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“…This can be inferred from its rotational barrier around the C À N bond. [6][7][8][9][10] In addition, amide bonds show a characteristic stability towards nucleophilic attack. [11,12] Energetic stability is also important because it confers the required degree of stability and rigidity to the amide/peptide linkage necessary to act as the protein scaffold.…”

Section: Introductionmentioning

confidence: 99%

Resonance Structures of the Amide Bond: The Advantages of Planarity

Mujika

Matxain

Eriksson

et al. 2006

Chemistry A European J

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Delocalization indexes based on magnitudes derived from electron-pair densities are demonstrated to be useful indicators of electron resonance in amides. These indexes, based on the integration of the two-electron density matrix over the atomic basins defined through the zero-flux condition, have been calculated for a series of amides at the B3LYP/6-31+G* level of theory. These quantities, which can be viewed as a measure of the sharing of electrons between atoms, behave in concordance with the traditional resonance model, even though they are integrated in Bader atomic basins. Thus, the use of these quantities overcomes contradictory results from analyses of atomic charges, yet keeps the theoretical appeal of using nonarbitrary atomic partitions and unambiguously defined functions such as densities and pair densities. Moreover, for a large data set consisting of 24 amides plus their corresponding rotational transition states, a linear relation was found between the rotational barrier for the amide and the delocalization index between the nitrogen and oxygen atoms, indicating that this parameter can be used as an ideal physical-chemical indicator of the electron resonance in amides.

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Crystallographic studies on retinoidal-active and -inactive aromatic anilides

Cited by 22 publications

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Distinctions of positional isomers of N-(methylthiazol-2-yl)nitrobenzamide by copper and iron ions

Distinctions of positional isomers of N-(methylthiazol-2-yl)nitrobenzamide by copper and iron ions

Orally Active, Nonpeptide Vasopressin V₂ Receptor Antagonists: A Novel Series of 1-[4-(Benzoylamino)benzoyl]-2,3,4,5-tetrahydro-1H-benzazepines and Related Compounds

Resonance Structures of the Amide Bond: The Advantages of Planarity

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Crystallographic studies on retinoidal-active and -inactive aromatic anilides

Cited by 22 publications

References 0 publications

Distinctions of positional isomers of N-(methylthiazol-2-yl)nitrobenzamide by copper and iron ions

Distinctions of positional isomers of N-(methylthiazol-2-yl)nitrobenzamide by copper and iron ions

Orally Active, Nonpeptide Vasopressin V2 Receptor Antagonists: A Novel Series of 1-[4-(Benzoylamino)benzoyl]-2,3,4,5-tetrahydro-1H-benzazepines and Related Compounds

Resonance Structures of the Amide Bond: The Advantages of Planarity

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Orally Active, Nonpeptide Vasopressin V₂ Receptor Antagonists: A Novel Series of 1-[4-(Benzoylamino)benzoyl]-2,3,4,5-tetrahydro-1H-benzazepines and Related Compounds