ChemInform Abstract: REACTIONS OF SODIUM BOROHYDRIDE IN ACIDIC MEDIA, IV. REDUCTION OF DIARYLMETHANOLS AND TRIARYLMETHANOLS IN TRIFLUOROACETIC ACID

Gribble, Gordon W.; Leese, Robert M.; Evans, B.

doi:10.1002/chin.197727182

Cited by 7 publications

(9 citation statements)

References 1 publication

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“…Compound 4d was prepared by the reaction of 4- n -hexylbenzoyl chloride with benzene and AlCl 3 to provide 28 (4- n -hexylphenyl)(phenyl)methanone. Trimethylsilyl cyanide was then employed in the preparation of the cyanohydrin 29 followed by reduction of the hydroxy group with NaBH 4 in TFA 25 to provide 30 (2-(4- n -hexylphenyl)-2-phenylacetonitrile). Reduction of the nitrile was then carried out using Raney Nickel under a hydrogen atmosphere to provide 4d in moderate yield.…”

Section: Resultsmentioning

confidence: 99%

Potential Modes of Interaction of 9-Aminomethyl-9,10-dihydroanthracene (AMDA) Derivatives with the 5-HT_2A Receptor: A Ligand Structure-Affinity Relationship, Receptor Mutagenesis and Receptor Modeling Investigation

et al. 2008

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The effects of 3-position substitution of 9-aminomethyl-9,10-dihydroanthracene (AMDA) on 5-HT2A receptor affinity were determined and compared to a parallel series of DOB-like 1-(2,5-dimethoxyphenyl)-2-aminopropanes substituted at the 4-position. The results were interpreted within the context of 5-HT2A receptor models that suggest that members of the DOB-like series can bind to the receptor in two distinct modes that correlate with the compounds’ functional activity. Automated ligand docking and molecular dynamics suggest that all of the AMDA derivatives, the parent of which is a 5-HT2A antagonist, bind in a fashion analogous to that for the sterically demanding antagonist DOB-like compounds. The failure of the F3406.52L mutation to adversely affect the affinity of AMDA and the 3-bromo derivative is consistent with the proposed modes of orientation. Evaluation of ligand-receptor complex models suggest that a valine/threonine exchange between the 5-HT2A and D2 receptors may be the origin of selectivity for AMDA and two substituted derivatives.

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Section: Resultsmentioning

confidence: 99%

Potential Modes of Interaction of 9-Aminomethyl-9,10-dihydroanthracene (AMDA) Derivatives with the 5-HT_2A Receptor: A Ligand Structure-Affinity Relationship, Receptor Mutagenesis and Receptor Modeling Investigation

et al. 2008

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“…15 Indeed, this reaction is also presumed to proceed via a carbocation intermediate. 16 A similar diastereoselectivity was obtained when (6aR,12R)-13/ (6aR,12S)-13 15 (40:60) was reduced with triethylsilane in TFA. The epimeric ratio obtained in these reactions seems to be a result of steric factors directing the nucleophilic attack (vide supra), the presumed intermediate cation being more accessible from the re-face of C12.…”

Section: Synthesismentioning

confidence: 57%

Derivatives of (R)-1,11-Methyleneaporphine: Synthesis, Structure, and Interactions with G-Protein Coupled Receptors

et al. 2000

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The design and synthesis of a well-characterized novel ring system, (R)-lambda1,11-methyleneaporphine [(R)-4], and 15 derivatives thereof are presented. The addition of various nucleophiles to (R)-lambda1,11-carbonylaporphine [(R)-11] or to the 1,11-hydroxymethyleneaporphine epimers gave separable mixtures of epimers. The epimeric ratios obtained in most reactions seem to be a result of steric factors directing the nucleophilic attack. The structure of the epimers was determined by a combination of X-ray crystallography (5 derivatives), NMR spectroscopy, and chemical correlation. Interesting and diverse pharmacological profiles of the derivatives were revealed through binding studies at serotonin 5-HT(7) and 5-HT(1A) receptors as well as at dopamine D(2A) receptors. Two derivatives appeared to be selective 5-HT(7) receptor antagonists. It is evident from our results that the novel ring system [(R)-4] provides a useful complement to other scaffolds available to medicinal chemists involved in studies of GPC receptors.

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“…Carbonyl can also be mildly reduced using triethylsilane and acid catalyst such as boron trifluoride etherate (BF 3 ·Et 2 O). Diarylketone can be easily converted into diarylmethane by Gribble reduction [ 110 ]. For anthracene-9,10-diones such as emodin, the reduction of carbonyls can be controlled to mono-reduction by SnCl 2 in mixed acid, and the carbonyl close to hydroxyl can be protected probably due to the intramolecular hydrogen bond [ 106 ].…”

Section: Structural Derivatization Strategies Of Natural Phenols By S...mentioning

confidence: 99%

Structural derivatization strategies of natural phenols by semi-synthesis and total-synthesis

Ding

Jiang

Zhang

et al. 2022

Nat. Prod. Bioprospect.

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Structural derivatization of natural products has been a continuing and irreplaceable source of novel drug leads. Natural phenols are a broad category of natural products with wide pharmacological activity and have offered plenty of clinical drugs. However, the structural complexity and wide variety of natural phenols leads to the difficulty of structural derivatization. Skeleton analysis indicated most types of natural phenols can be structured by the combination and extension of three common fragments containing phenol, phenylpropanoid and benzoyl. Based on these fragments, the derivatization strategies of natural phenols were unified and comprehensively analyzed in this review. In addition to classical methods, advanced strategies with high selectivity, efficiency and practicality were emphasized. Total synthesis strategies of typical fragments such as stilbenes, chalcones and flavonoids were also covered and analyzed as the supplementary for supporting the diversity-oriented derivatization of natural phenols.

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ChemInform Abstract: REACTIONS OF SODIUM BOROHYDRIDE IN ACIDIC MEDIA, IV. REDUCTION OF DIARYLMETHANOLS AND TRIARYLMETHANOLS IN TRIFLUOROACETIC ACID

Cited by 7 publications

References 1 publication

Potential Modes of Interaction of 9-Aminomethyl-9,10-dihydroanthracene (AMDA) Derivatives with the 5-HT_2A Receptor: A Ligand Structure-Affinity Relationship, Receptor Mutagenesis and Receptor Modeling Investigation

Potential Modes of Interaction of 9-Aminomethyl-9,10-dihydroanthracene (AMDA) Derivatives with the 5-HT_2A Receptor: A Ligand Structure-Affinity Relationship, Receptor Mutagenesis and Receptor Modeling Investigation

Derivatives of (R)-1,11-Methyleneaporphine: Synthesis, Structure, and Interactions with G-Protein Coupled Receptors

Structural derivatization strategies of natural phenols by semi-synthesis and total-synthesis

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ChemInform Abstract: REACTIONS OF SODIUM BOROHYDRIDE IN ACIDIC MEDIA, IV. REDUCTION OF DIARYLMETHANOLS AND TRIARYLMETHANOLS IN TRIFLUOROACETIC ACID

Cited by 7 publications

References 1 publication

Potential Modes of Interaction of 9-Aminomethyl-9,10-dihydroanthracene (AMDA) Derivatives with the 5-HT2A Receptor: A Ligand Structure-Affinity Relationship, Receptor Mutagenesis and Receptor Modeling Investigation

Potential Modes of Interaction of 9-Aminomethyl-9,10-dihydroanthracene (AMDA) Derivatives with the 5-HT2A Receptor: A Ligand Structure-Affinity Relationship, Receptor Mutagenesis and Receptor Modeling Investigation

Derivatives of (R)-1,11-Methyleneaporphine: Synthesis, Structure, and Interactions with G-Protein Coupled Receptors

Structural derivatization strategies of natural phenols by semi-synthesis and total-synthesis

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Product

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Potential Modes of Interaction of 9-Aminomethyl-9,10-dihydroanthracene (AMDA) Derivatives with the 5-HT_2A Receptor: A Ligand Structure-Affinity Relationship, Receptor Mutagenesis and Receptor Modeling Investigation

Potential Modes of Interaction of 9-Aminomethyl-9,10-dihydroanthracene (AMDA) Derivatives with the 5-HT_2A Receptor: A Ligand Structure-Affinity Relationship, Receptor Mutagenesis and Receptor Modeling Investigation