Selective Monoformylation Of 1,3-Diaminopropane Derivatives

Orelli, Liliana R.; García, María B.; Niemevz, Fernando; Perillo, Isabel A.

doi:10.1080/00397919908086172

Cited by 16 publications

(9 citation statements)

References 25 publications

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“…Applying the same chemistry, bis(amides) 5a–g of aminoxyacetic acid (Table 2) with various aromatic substitution patterns were also prepared. Monoamine 8 was prepared by alkylation of 4-chloroaniline with 3-bromopropylamine 6 15, followed by acylation with bis(trifluoromethyl)benzoyl chloride (Scheme 2). The regioisomeric monoamine 11 was synthesized by alkylation of bis(trifluoromethyl)benzylamine with bromide 10 , which was prepared by acylation of 4-chloroaniline with 3-bromopropionyl chloride (Scheme 3).…”

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confidence: 99%

Design, synthesis and prostate cancer cell-based studies of analogs of the Rho/MKL1 transcriptional pathway inhibitor, CCG-1423

Evelyn

Bell

Ryu

et al. 2010

Bioorganic & Medicinal Chemistry Letters

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We recently identified bis(amide) CCG-1423 (1) as a novel inhibitor of RhoA/C-mediated gene transcription that is capable of inhibiting invasion of PC-3 prostate cancer cells in a Matrigel model of metastasis. An initial structure-activity relationship study focusing on bioisosteric replacement of the amides and conformational restriction identified two compounds, 4g and 8, with improved selectivity for inhibition of RhoA/C-mediated gene transcription and attenuated cytotoxcity relative to 1. Both compounds were also capable of inhibiting cell invasion with equal efficacy to 1 but with less attendant cytotoxicity.

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confidence: 99%

Design, synthesis and prostate cancer cell-based studies of analogs of the Rho/MKL1 transcriptional pathway inhibitor, CCG-1423

Evelyn

Bell

Ryu

et al. 2010

Bioorganic & Medicinal Chemistry Letters

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“…In the tetrahydropyrimidine, the presence of a phenyl substituent on N1 results in a cross-conjugated system where competitive amidine and arylamine-type electron delocalization are possible (Scheme II, structures I and II, respectively). A comparison between the aromatic chemical shifts of compound 2a and N-phenyltrimethylenediamine (H2: 6.44, H3,5: 7.17, H4: 6.69 ppm) [14] shows that shielding of the ortho and para hydrogen atoms is less significative in the amidine. This would be the consequence of competitive amidine-like resonance, enhanced by steric hindrance of the vicinal 2-tert-butyl group, which forces the phenyl group out of the plane of the amidine system.…”

Section: Resultsmentioning

confidence: 99%

Synthesis, NMR characterization andab initio6-31G* study of 1-aryl-2,3-dialkyl-1,4,5,6-tetrahydropyrimidinium salts

Niemevz

Link

Perillo

et al. 2005

Journal of Heterocyclic Chemistry

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We describe the synthesis of a series of 1-aryl-2,3-dialkyl-1,4,5,6-tetrahydropyrimidinium salts 1, by alkylation of the corresponding 1,4,5,6-tetrahydropyrimidines 2. We analyze the changes in the 1 H and 13 C NMR spectra of compounds 2 induced by protonation and quaternization. The results of an ab initio theoretical study on amidine 2a, and the cations resulting from its protonation (2aH + ) and quaternization (1a + ) are presented. A qualitative correlation was found between 13 C NMR and theoretical data in the case of protonation. The influence of the substitution patterns in the 1 H and 13 C NMR spectra of compounds 1 is also discussed.

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“…N-aryl-1,3-propanediamines 2 were obtained according to the literature procedure [16]. Yields, physical data and elemental analyses of new compounds are as follows.…”

Section: Synthesis Characterization and Biological Activitymentioning

confidence: 99%

Synthesis, characterization and biological activity of bis(3‐Aryl‐1‐hexahydropyrimidinyl)methanes. Novel heterocyclic polyamine derivatives

Bisceglia

García

Massa

et al. 2004

Journal of Heterocyclic Chem

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A method is described for the synthesis of bis(3-aryl-1-hexahydropyrimidinyl)methanes 1, by condensation of N-aryl-1,3-propanediamines 2 with formaldehyde. The reaction mechanism involves N-arylhexahydropyrimidines 3 as intermediates. Such compounds can also be prepared efficiently by a methylene exchange reaction between bis-hexahydropyrimidines 1 and the corresponding diamines 2. The antimicrobial activity of compounds 1 was evaluated by the disk diffusion method and some of them showed moderate to good growth inhibition activity.

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Selective Monoformylation Of 1,3-Diaminopropane Derivatives

Cited by 16 publications

References 25 publications

Design, synthesis and prostate cancer cell-based studies of analogs of the Rho/MKL1 transcriptional pathway inhibitor, CCG-1423

Design, synthesis and prostate cancer cell-based studies of analogs of the Rho/MKL1 transcriptional pathway inhibitor, CCG-1423

Synthesis, NMR characterization andab initio6-31G* study of 1-aryl-2,3-dialkyl-1,4,5,6-tetrahydropyrimidinium salts

Synthesis, characterization and biological activity of bis(3‐Aryl‐1‐hexahydropyrimidinyl)methanes. Novel heterocyclic polyamine derivatives

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