Reactions of Sodium Borohydride in Acidic Media; XVI.<sup>1</sup>
                  <i>N</i>-Methylation of Amines with Paraformaldehyde/Trifluoroacetic Acid

Gribble, Gordon W.; Nutaitis, Charles F.

doi:10.1055/s-1987-28053

Cited by 79 publications

(31 citation statements)

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“…The resulting amines ( 3a–k ) were methylated using paraformaldehyde/NaBH 4 /TFA. 18 The methoxybenzylaminomorphinans ( 3a–c , 3f–h ) were demethylated with BBr 3 in anhydrous CH 2 Cl 2 to yield hydroxybenzylaminomorphinan ligands ( 4a–c , 4d–f ). For the synthesis of morphine analogues (Scheme 2), morphine was treated with 1 equivalent of PhNTf 2 and Et 3 N in dichloromethane to selectively afford morphine-3-triflate 7 .…”

Section: Chemistrymentioning

confidence: 99%

Synthesis, Binding Affinity, and Functional in Vitro Activity of 3-Benzylaminomorphinan and 3-Benzylaminomorphine Ligands at Opioid Receptors

Neumeyer

Zhang

et al. 2012

J. Med. Chem.

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A series of 3-benzylamino-3-desoxymorphinan (I) and 3-benzylamino-3-desoxymorphine (II) derivatives were synthesized and evaluated for their binding affinities and functional activity data are presented at MOR, KOR, and DOR. Some of these ligands were found to have high binding affinity at MOR and KOR, and displayed increased selectivity at MOR over KOR and DOR compared to butorphan or cyclorphan. The most selective compound, 3-(3′-hydroxybenzyl)amino-17-methylmorphinan (4g) (24-fold MOR to KOR and 1700-fold MOR to DOR) also showed high binding affinity (0.42 nM to MOR), and was a full agonist in the [35S]GTPγS binding assay. 2-(3′-Hydroxybenzyl)amino-17-cyclopropylmethylmorphinan (17) was found to be a KOR-selective ligand (150-fold over MOR and >10,000-fold over the DORs). Most 3-benzylaminomorphinan derivatives were partial agonists at MOR and full agonists at KOR in the [35S]GTPγS binding assay.

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Section: Chemistrymentioning

confidence: 99%

Synthesis, Binding Affinity, and Functional in Vitro Activity of 3-Benzylaminomorphinan and 3-Benzylaminomorphine Ligands at Opioid Receptors

Neumeyer

Zhang

et al. 2012

J. Med. Chem.

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“…Reaction of (R)-8 with formaldehyde and sodium borohydride in trifluoroacetic acid gave (R)-12 23) . Treatment of (R)-12 with two equivalents of BuLi followed by the addition of iodine formed (R)-13.…”

Section: Synthesis Of the Optically Active 119-binaphthyl-229-diamimentioning

confidence: 99%

Synthesis of chiral conjugated propeller-like polymers using optically active 1,1′-binaphthyl-2,2′-diamine derivatives

Cheng

Pu²

1999

Macromol. Chem. Phys.

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SUMMARY: Synthetic methods are developed to prepare the optically active derivatives of 1,19-binaphthyl-2,29-diamine by specific substitution at the 6,69-positions and by tetraalkylation of the diamine groups. These optically active binaphthyldiamine compounds are used to build the propeller-like polymers by using the transition metal-catalyzed cross-coupling of aryl halides with terminal alkenes or alkynes. The resulting chiral conjugated aryleneethynylene and arylenevinylene polymers show significantly different UV and CD features from their 1,19-bi-2-naphthol-based polymer analogs.

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“…15 Treatment of 13a and 13c with paraformaldehyde and NaBH 4 yielded dimethyl substituted aminothiazolomorphinans 17a and 17c in 83–89% yields 16. N′-Trifluoroethyl derivative 15 was prepared in 45% yield by treating 3 with trifluoroacetic anhydride in the presence of Et 3 N, followed by reduction 17.…”

Section: Chemistrymentioning

confidence: 99%

Aminothiazolomorphinans with Mixed κ and μ Opioid Activity

et al. 2011

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A series of N-substituted and N′-substituted aminothiazole-derived morphinans (5) were synthesized for expanding the structure-activity relationships of aminothiazolo-morphinans. Although their affinities were somewhat lower than their prototype aminothiazolo-Ncyclopropylmorphinan (3), 3-aminothiazole derivatives of cyclorphan (1) containing a primary amino group displayed high affinity and selectivity at the κ and μ opioid receptors. [ 35 S]GTPγS binding assays showed that the aminothiazolomorphinans were κ agonists with mixed agonist and antagonist activity at the μ opioid receptor. These novel N′-monosubstituted aminothiazolederived morphinans may be valuable for the development of drug abuse medications.

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Reactions of Sodium Borohydride in Acidic Media; XVI.¹ N-Methylation of Amines with Paraformaldehyde/Trifluoroacetic Acid

Cited by 79 publications

References 0 publications

Synthesis, Binding Affinity, and Functional in Vitro Activity of 3-Benzylaminomorphinan and 3-Benzylaminomorphine Ligands at Opioid Receptors

Synthesis, Binding Affinity, and Functional in Vitro Activity of 3-Benzylaminomorphinan and 3-Benzylaminomorphine Ligands at Opioid Receptors

Synthesis of chiral conjugated propeller-like polymers using optically active 1,1′-binaphthyl-2,2′-diamine derivatives

Aminothiazolomorphinans with Mixed κ and μ Opioid Activity

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Reactions of Sodium Borohydride in Acidic Media; XVI.1 N-Methylation of Amines with Paraformaldehyde/Trifluoroacetic Acid

Cited by 79 publications

References 0 publications

Synthesis, Binding Affinity, and Functional in Vitro Activity of 3-Benzylaminomorphinan and 3-Benzylaminomorphine Ligands at Opioid Receptors

Synthesis, Binding Affinity, and Functional in Vitro Activity of 3-Benzylaminomorphinan and 3-Benzylaminomorphine Ligands at Opioid Receptors

Synthesis of chiral conjugated propeller-like polymers using optically active 1,1′-binaphthyl-2,2′-diamine derivatives

Aminothiazolomorphinans with Mixed κ and μ Opioid Activity

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Reactions of Sodium Borohydride in Acidic Media; XVI.¹ N-Methylation of Amines with Paraformaldehyde/Trifluoroacetic Acid