16675-58-4

Usage

Class

Phenylpiperidines

Structural Similarity

Similar to fentanyl and its analogs

Core Structure

Tetrahydropyridine

Attached Groups

a. Benzyl group
b. Pyrrolidin-1-yl group

Pharmacological Effects

a. Potential use as an opioid analgesic
b. Potential use as a cocaine antagonist

Research Findings

a. May have abuse potential
b. Can produce similar effects to other opioids

Field of Interest

Medicinal chemistry and drug development

InChI:InChI=1/C16H22N2/c1-2-6-15(7-3-1)14-17-12-8-16(9-13-17)18-10-4-5-11-18/h1-3,6-8H,4-5,9-14H2

Upstream product

• 123-75-1 pyrrolidine 
• 3612-20-2 1-phenylmethyl-4-piperidone 

Downstream Products

• 52336-92-2 3-((1H-indol-3-yl)methyl)-1-benzylpiperidin-4-one 

Relevant academic research and scientific papers

Domino Synthesis of Benzo-Fused β,γ-Unsaturated Ketones from Alkenylboronic Acids and N-Tosylhydrazone-Tethered Benzonitriles

The transition-metal-free domino reaction between alkenylboronic acids and N-tosylhydrazones from o-(2-oxoalkyl)- and o-(3-oxoalkyl)benzonitriles leads to β, γ-unsaturated indanones and tetralones featuring an α-"all-carbon" quaternary center. The employment of derivatives of α-substituted cyclopentanones and cyclohexanones led to the stereoselective preparation of β, γ-unsaturated tetrahydrocyclopenta[a]inden-8(1H)-ones, hexahydrofluorenones, and hexahydroanthracenones as cis-fused single stereoisomers. A domino sequence involving diazo compound formation/reductive alkenylation/1,3-borotropic rearrangement/intramolecular bora-aza-ene reaction is proposed to justify the formation of the products as well as the stereoselectivity.

Substituted amide compound and application

The invention belongs to the field of agricultural bactericidal, insecticidal and acaricidal agents, and relates to a substituted amide compound and an application. The substituted amide compound has a structure as shown in a general formula I in the specification; and in the general formula I, substituents are defined in the specification. The compound provided by the invention has broad-spectrum bactericidal, insecticidal and acaricidal activities, has excellent control effects on diseases like cucumber downy mildew, corn rust, wheat powdery mildew and rice blast, especially has better control effects on the corn rust, also has excellent control effects on aphids and Tetranychus cinnabarinus, and especially can obtain good effects on the Tetranychus cinnabarinus at a low dosage.

Substituted tetrahydroisoquinoline compound and application

The invention discloses a substituted tetrahydroisoquinoline compound and application. The compound has a structure as shown in a general formula I in the specification; and in the general formula I, substituents are defined in the specification. The comp

ANTI-PULMONARY TUBERCULOSIS NITROIMIDAZOLE DERIVATIVE

Disclosed is a substituted nitroimidazole derivative, which is mainly used for treating related diseases caused by mycobacterial infections, such as Mycobacterium tuberculosis, especially being suitable for diseases caused by resistant Mycobacterium tuberculosis.

A concise one-pot synthesis of trifluoromethyl-containing 2,6-disubstituted 5,6,7,8-tetrahydroquinolines and 5,6,7,8-tetrahydronaphthyridines

5,6,7,8-Tetrahydroquinolines and 5,6,7,8-tetrahydronaphthyridines with appended trifluoromethyl groups are valuable chemotypes in medicinal chemistry due to the presence of a partially-saturated bicyclic ring and metabolically-stable CF3 group. 1H NMR studies were used to optimize the preparation of such compounds, using a three-step/one-pot procedure, to provide novel 2,6-disubstitued derivatives with a tertiary-substituent. Racemic 2,6-disubstituted tetrahydroquinolines were separated by chiral HPLC to provide single enantiomers.

NAPHTHYRIDINE DERIVATIVES AS POTASSIUM CHANNEL MODULATORS

This invention provided compounds of formula (I), where W and Z are, independently, CH or N, and where other substituents are defined herein. Such compounds are potassium channel modulators. The invention also provides a composition comprising a pharmaceu

Stereoselective synthesis of a MCHr1 antagonist

(Chemical Equation Presented) Melanin-concentrating hormone (MCH) is implicated in the feeding behavior in mammals affording a potential target to control overeating in people. Compound 1 (AMG 076) has been identified as a potent MCHr1 antagonist for the

Antinociceptive effects of N-acyloctahydropyrido[3,2,1-ij][1,6] naphthyridine in mice: Structure-activity relation study of matrine-type alkaloids part II

N-Acyloctahydropyrido[3,2,1-ij][1,6]naphthyridines were synthesized as derivatives of matrine-type alkaloids, and the structure-activity relations were examined by the acetic acid-induced abdominal contraction test. The antinociceptive potencies of N-acyl

Synthesis of classical and nonclassical, partially restricted, linear, tricyclic 5-deaza antifolates

Seven novel 2,4-diamino-5-deaza-6,7,8,9-tetrahydropyrido[3,4-g]pteridine derivatives 3-9 with different benzyl and a benzoyl substitution at the N7 position were designed and synthesized, as classical and nonclassical, partially restricted, linear tricyclic 5-deaza antifolates. The purpose was to investigate the effect of conformational restriction of the C6-C9 (τ1) and C9-N10 (τ2) bonds via an ethyl bridge from the N10 to the C7 position of 5-deaza methotrexate (MTX) on the inhibitory potency against dihydrofolate reductase (DHFR) from different sources and on antitumor activity. The synthetic methodology for most of the target compounds was a concise five-step total synthesis to construct the tricyclic nucleus, 2,4-diamino-5-deaza-7H-6,7,8,9tetrahydropyrido[3,4-g]pteridine (23), followed by regioselective alkylation of the N7 nitrogen. Biological results indicated that this partial conformational modification for the classical analogue N-[4-[(2,4-diamino-5-deaza-6,7,8,9-tetrahydropyrido[3, 4-g]pteridin-7-yl)methyl]benzoyl]-L-glutamic acid 3 was detrimental to DHFR inhibitory activity as well as to antitumor activity compared to MTX or 5-deaza MTX. However, the classical analogue 3 was a better substrate for folypolyglutamate synthetase (FPGS) than MTX. These results show that a classical 5-deaza folate partially restricted via a bridge between the N10 and C7 positions retains FPGS substrate activity and that the antitumor activity of classical tricyclic analogues such as 3 would be influenced by FPGS levels in tumor systems. Interestingly, the nonclassical analogues 4-9 showed moderate to good selectivity against DHFR from pathogenic microbes compared to recombinant human DHFR. These results support the idea that removal of the 5-methyl group of piritrexim along with restriction of τ1 and τ2 can translate into selectivity for DHFR from pathogens.

Conformational Study of Bridgehead Lactams. Preparation and X-Ray Structural Analysis of 1-Azabicyclononane-2,6-dione

3-(2-carboxyethyl)-4-piperidone (5) prepared, from N-benzyl-4-piperidone and benzyl acrylate (9), was thermally cyclized in the presence of dibutyltin oxide to 1-azabicyclononane-2,6-dione (4), which possesses a bridgehead amide nitrogen.The boat-chair conformation of (4) in the solid state has been characterized by X-ray crystal structure analysis and the bridgehead amide shown to be appreciably distorted from planarity, with N(1) displaced by 0.37 Angstroem from the plane of C(2), C(8), and C(9).Crystallographic data are a=6.214(4), b=6.845(5), c=17.850(8) Angstroem, Z=4, space group P21cn.X-Ray intensity measurements were made on a four-circle diffractometer and least-squares adjustment of the atomic parameters converged at R=0.038 for 1004 reflections.