The effect of ring size in N-benzoyl saturated heterocyclic amides

Fong, CW; Grant, HG

doi:10.1071/ch9812307

Cited by 25 publications

(9 citation statements)

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“…Assignment of signals was assisted by correlation spectroscopy (COSY), distortionless enhancement by polarization transfer (DEPT), heteronuclear single quantum coherence (HSQC), and heteronuclear multiple bond correlation (HMBC) experiments where necessary. For compounds containing saturated heterocyclic amides ( 5 – 8 , 11 – 14 ), severe exchange broadening of the amide α‐ and β‐carbon signals was observed, consistent with previous characterization of analogous systems …”

Section: Methodssupporting

confidence: 90%

The chemistry and pharmacology of putative synthetic cannabinoid receptor agonist (SCRA) new psychoactive substances (NPS) 5F‐PY‐PICA, 5F‐PY‐PINACA, and their analogs

Banister

Kevin

Martin

et al. 2019

Drug Testing and Analysis

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5F‐PY‐PICA and 5F‐PY‐PINACA are pyrrolidinyl 1‐(5‐fluoropentyl)ind (az)ole‐3‐carboxamides identified in 2015 as putative synthetic cannabinoid receptor agonist (SCRA) new psychoactive substances (NPS). 5F‐PY‐PICA, 5F‐PY‐PINACA, and analogs featuring variation of the 1‐alkyl substituent or contraction, expansion, or scission of the pyrrolidine ring were synthesized and characterized by nuclear magnetic resonance (NMR) spectroscopy and liquid chromatography–quadrupole time‐of‐flight–mass spectrometry (LC–QTOF–MS). In competitive binding experiments against HEK293 cells expressing human cannabinoid receptor type 1 (hCB1) or type 2 (hCB2), all analogs showed minimal affinity for CB1 (pKi < 5), although several demonstrated moderate CB2 binding (pKi 5.45–6.99). In fluorescence‐based membrane potential assays using AtT20‐hCB1 or ‐hCB2 cells, none of the compounds (at 10 μM) produced an effect >50% of the classical cannabinoid agonist CP55,940 (at 1 μM) at hCB1, although several showed slightly higher relative efficacy at hCB2. Expansion of the pyrrolidine ring of 5F‐PY‐PICA to an azepane (8) conferred the greatest hCB2 affinity (pKi 6.99) and activity (pEC50 7.54, Emax 72%) within the series. Unlike other SCRA NPS evaluated in vivo using radio biotelemetry, 5F‐PY‐PICA and 5F‐PY‐PINACA did not produce cannabimimetic effects (hypothermia, bradycardia) in mice at doses up to 10 mg/kg.

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Section: Methodssupporting

confidence: 90%

The chemistry and pharmacology of putative synthetic cannabinoid receptor agonist (SCRA) new psychoactive substances (NPS) 5F‐PY‐PICA, 5F‐PY‐PINACA, and their analogs

Banister

Kevin

Martin

et al. 2019

Drug Testing and Analysis

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“…Moreover, the deshielding magnitude of anti α protons is also higher (≈ 1 ppm) than the anti α axial protons. With a view to determining the 13 C substituent parameters of the formyl, acetyl and benzoyl substituents at nitrogen in the six-membered ring compounds, the chemical shifts of N-formylpiperidine 12 , Nacetylpiperidine 13 and N-benzoylpiperidine 14 are compared with that of the parent piperidine and the parameters are displayed in Table-4. It is seen from Table -4 that syn α carbons are shielded to 5-7 ppm due to N-acylation.…”

Section: Analysis Of Chemical Shiftsmentioning

confidence: 99%

Synthesis and Spectral Characterization of Some Novel N-Acyl-Piperidin-4-Ones

Selvaraju¹,

Manimekalai²

2017

Rasayan J. Chem.

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A collection of novel N-acyl-t(3)-ethyl-r(2),c(6)-di(2'-furyl)piperidin-4-ones 1-4 are synthesized, characterized by melting point, one-dimensional NMR ( 1 H and 13 C) and two-dimensional NOESY and 1 H-13 C COSY spectrum. The spectra reveal the presence of two isomeric forms i.e., E and Z isomers for 1-4. The effect of varying the substituents at nitrogen on the 1 H and 13 C chemical shifts have been analyzed in detail.

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“…On the other hand, for cyclopropane a value of 16 Hz was calculated for carbon-carbon coupling while a somewhat lower value of 10 Hz was observed for the carboxylic acid of cyclopropane [19]. However, a more recent 13C nmr assessment of the lone pair at nitrogen in N-benzoylaziridine is that it is pyramidal [22]. Further, the 'J ("N, "C) values obtained are indicative of high "p" character in the endocyclic C,-N and C,-N bonds; INDO-MO calculations of Wasylischen [ l 11 have indicated approximately 80% "p" character.…”

Section: 2(2)mentioning

confidence: 99%

ChemInform Abstract: Solid‐State Structures of cis‐ and trans‐1‐Cyclohexyl‐2‐phenyl‐3(p‐toluyl)aziridines.

Tarburton¹,

Day²,

DAY³

et al. 1986

Chemischer Informationsdienst

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Solid‐state structures have been determined for cis‐ and trans‐1‐cyclohexyl‐2‐phenyl‐3‐(p‐toluyl)aziridines using single‐crystal X‐ray diffraction techniques. The cis isomer crystallizes in the centrosymmetric monoclinic space group P21/c (No. 14), with a = 18.669(3)Å, b = 5.709(1)Å, c = 17.412(2)Å, β = 96.29(1)° and Z = 4; the trans isomer crystallizes in the noncentrosymmetric orthorhombic space group Pna21 (No. 33), with a = 17.089(2)Å, b = 18.729(3)Å, c = 5.749(1)Å and Z = 4. Full‐matrix least‐squares refinement of the structural parameters led to the following final agreement factors: R1 (unweighted, based on F) = 0.040 and R2 (weighted, based on F) = 0.054 for the 2592 independent reflections of the cis isomer having 2θMoK¯α <55° and I>3σ1, and R1 = 0.033 and R2 = 0.031 for the 1504 independent reflections of the trans isomer having 2θMoK¯α <55° and I>3σ1. The statistically significant differences that exist between the two isomers for two bond lengths and ten bond angles (p < 0.05) appear to be the direct result of the p‐toluyl group orientation with respect to the cyclohexyl and phenyl substituents. In the cis isomer it is anti with respect to the N‐cyclohexyl group and cis with respect to the phenyl group, whereas in the trans isomer it is syn with respect to the N‐cyclohexyl and trans with respect to the phenyl group. Three‐ring to carbonyl hyperconjugation is correlated with stereoelectronic interactions in the trans isomer. Bonding, determined by X‐ray and nmr studies, is discussed for the three‐membered aziridine ring proper; while bonding, determined by X‐ray studies, is discussed for substituents of the aziridine ring. These aziridinyl ketone compounds are of importance as potential mammalian DNA alkylating anti‐tumor agents in solid‐state solid‐state systems. To date only a trans isomer has demonstrated this biological activity in tumor‐bearing rats.

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The effect of ring size in N-benzoyl saturated heterocyclic amides

Cited by 25 publications

References 0 publications

The chemistry and pharmacology of putative synthetic cannabinoid receptor agonist (SCRA) new psychoactive substances (NPS) 5F‐PY‐PICA, 5F‐PY‐PINACA, and their analogs

The chemistry and pharmacology of putative synthetic cannabinoid receptor agonist (SCRA) new psychoactive substances (NPS) 5F‐PY‐PICA, 5F‐PY‐PINACA, and their analogs

Synthesis and Spectral Characterization of Some Novel N-Acyl-Piperidin-4-Ones

ChemInform Abstract: Solid‐State Structures of cis‐ and trans‐1‐Cyclohexyl‐2‐phenyl‐3(p‐toluyl)aziridines.

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