Orally active CCR5 antagonists as anti-HIV-1 agents. Part 3: Synthesis and biological activities of 1-benzazepine derivatives containing a sulfoxide moiety

Seto, Masaki; Miyamoto, Naoki; Aikawa, Katsuji; Aramaki, Yoshio; Kanzaki, Naoyuki; Iizawa, Yuji; Baba, Masanori; Shiraishi, Masayuki

doi:10.1016/j.bmc.2004.10.021

Cited by 98 publications

(61 citation statements)

References 27 publications

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“…Examples of benzazepine derivatives with pharmacological interest are the 1H-2-benzazepine derivative 38, which is an inhibitor of acetylcholinesterase [30], and the potential anti-HIV agent 39 [31]. Examples of dibenzazepines include imipramine (40) and clomipramine (41), two 10,11-dihydrodibenz [b,f ]azepine alkaloids that have been used for the treatment of depressive disorders [32], perlapine (42), a dibenzo [b,e]azepine with antipsychotic and sedative activities [33], and azapetine (43), an antiadrenergic dibenzo [c,e]azepine [34].…”

Section: Relevant Natural and Useful Compoundsmentioning

confidence: 99%

Seven‐Membered Heterocycles: Azepines, Benzo Derivatives and Related Systems

Vaquero

Cuadro

Herradón

2011

Modern Heterocyclic Chemistry

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The replacement of a carbon atom by a heteroatom in a seven-membered carbocycle leads to the corresponding seven-membered heterocyclic ring system. Different types of heterocycles can be formed depending on the nature of the carbocycle. In a cycloheptatriene the replacement can involve any of the six sp 2 hybridized carbons or the sp 3 carbon atom, whereas in cycloheptane all carbon atoms are equivalent and replacement affords exclusively the fully saturated heterocyclic systems. Partially saturated seven-membered heterocycles can be viewed as derivatives or related systems of these two main seven-membered heterocyclic units arising from carbon replacement in cycloheptatriene and in cycloheptane. Replacement of the sp 3 hybridized carbon atom in cycloheptatriene by a nitrogen leads to an azacycloheptatriene known as 1H-azepine (1) and the corresponding 2H-, 3H-, and 4H-azepines (2-4) are the tautomeric forms generated by the replacement of the sp 2 carbons. 1H-Azepine is an unstable red oil that is prone to rearrange to the also unstable 3H-azepine in the presence of acids and bases. However, this tautomer seems to be more stable than both 4H-and 2H-azepine. The structures related to 1H-azepine that bear an oxygen or sulfur atom are known as oxepine (5) and thiepine (6) (thiepin is favored by Chemical Abstracts Service). Oxepine is much more stable than thiepine and has been synthesized, isolated, and characterized at room temperature while thiepine has not been detected to date. Stable monocyclic thiepines were prepared and characterized in the 1980s. Azepines, oxepines, and thiepines that are constrained to planar or almost planar conformations should be antiaromatic molecules with negative resonance energy and, as a consequence, these compounds are unknown.The fully saturated seven-membered heterocycle containing one nitrogen is azepane (7) (hexahydroazepine or perhydroazepine); the oxygen and sulfur analogues are known as oxepane (8) and thiepane (9). All of these compounds are stable and show typical behavior of secondary amine, ether and thioether, respectively. TwoModern Heterocyclic Chemistry, First Edition. Edited

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Section: Relevant Natural and Useful Compoundsmentioning

confidence: 99%

Seven‐Membered Heterocycles: Azepines, Benzo Derivatives and Related Systems

Vaquero

Cuadro

Herradón

2011

Modern Heterocyclic Chemistry

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“…Dichas moléculas han sido estudiadas por su efecto sobre el coreceptor CCR5, un receptor de quimiocina situado sobre monocitos y linfocitos y que es utilizado por el VIH-1 para ingresar a la célula diana. Al actuar como ligandos del CCR5 los derivados de las 1-benzazepinas que contienen un grupo metileno entre el sulfóxido y el grupo 2-piridil, han mostrado un incremento en la actividad farmacológica, causando un mayor efecto inhibitorio de la interacción del virus con el receptor y evitando por tanto la entrada del virus a la célula (Seto et al, 2005).…”

Section: Derivados De Las 1-benzoazepinasunclassified

Search for synthetic and natural substances with in vitro bioactivity against Mycobacterium tuberculosis. Part I

Moreno¹,

Ribón²

2017

JOSHA

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“…[33][34][35][36] The main advantages of our approach reside in the use of a catalytic amount of the metal complex, in the high chemical yields achievable, and in the unprecedented high ee's (up to 99%) obtained with benzyl alkyl sulfoxides. Thanks to its reliability and efficiency, this procedure has been employed by other groups in the preparation of valuable chiral drugs, 37,38 and it constitutes the key step of an efficient protocol for the preparation of optically active dialkylsulfoxides by substitution at sulfur. 39,40 Furthermore, by the same procedure a large class of alkyl aryl sulfoxides, having different structure, have been prepared allowing us to set up efficient methods of analysis of their chiroptical properties and to develop new nonempirical approaches for the assignment of absolute configuration of chiral sulfoxides.…”

Section: Introductionmentioning

confidence: 99%

Enantioselective oxidation of sulfides catalyzed by titanium complexes of 1,2‐diarylethane‐1,2‐diols: Effect of the aryl substitution

et al. 2008

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The effects of the substitution on the aryl moiety on the asymmetric oxidation of sulfides mediated by Ti-complexes of chiral 1,2-diarylethane-1,2-diols were investigated. The substitution of the aryl ring of the diol with both EWG and EDG substituents generally decreased the enantioselectivity with respect to the use of unsubstituted 1,2-diphenylethane-1,2-diol (1a). Only in the presence of 1,2-di(4-t-butyl)phenyl-1,2-diol (1g) were higher ee's obtained with aryl methyl and aryl benzyl sulfides affording ee's up to 90 and 99%, respectively. Lower ee's were achieved with larger naphthyl and aryl alkyl sulfides. Contrary to the other Ti-alcoholates used in the oxidation of sulfides, the Ti-complex of diol 1g was soluble in hexane, allowing us to perform the process with high enantioselectivity in this solvent, with great environmental advantages over the commonly used chlorinated solvents.

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Orally active CCR5 antagonists as anti-HIV-1 agents. Part 3: Synthesis and biological activities of 1-benzazepine derivatives containing a sulfoxide moiety

Cited by 98 publications

References 27 publications

Seven‐Membered Heterocycles: Azepines, Benzo Derivatives and Related Systems

Seven‐Membered Heterocycles: Azepines, Benzo Derivatives and Related Systems

Search for synthetic and natural substances with in vitro bioactivity against Mycobacterium tuberculosis. Part I

Enantioselective oxidation of sulfides catalyzed by titanium complexes of 1,2‐diarylethane‐1,2‐diols: Effect of the aryl substitution

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