N-Isocyaniminotriphenylphosphorane (Ph3PNNC) as an Efficient Reagent for the Synthesis of Fully Substituted 1,3,4-Oxadiazoles from 3-Phenyl-2-Propynoic Acid, Secondary Amines and Aromatic Bis-Aldehydes

2013 ◽  
Vol 188 (7) ◽  
pp. 886-894 ◽  
Author(s):  
Hamideh Ahankar ◽  
Ali Ramazani ◽  
Yavar Ahmadi ◽  
Issa Amini
Keyword(s):  
Secondary Amines ◽  
Propynoic Acid ◽  
Efficient Reagent

Acceptorless amine dehydrogenation and transamination using Pd-doped layered double hydroxides

2018 ◽  
Author(s):  
Diana Ainembabazi ◽  
Nan An ◽  
Jinesh Manayil ◽  
Kare Wilson ◽  
Adam Lee ◽  
...  
Keyword(s):  
Layered Double Hydroxides ◽  
Oxidation States ◽  
Secondary Amines ◽  
Primary Amines ◽  
Acid Dissolution ◽  
Oxidative Amination ◽  
Strong Function ◽  
Excellent Activity ◽  
High Yields ◽  
Double Hydroxides

<div> <p>The synthesis, characterization, and activity of Pd-doped layered double hydroxides (Pd-LDHs) for for acceptorless amine dehydrogenation is reported. These multifunctional catalysts comprise Brønsted basic and Lewis acidic surface sites that stabilize Pd species in 0, 2+, and 4+ oxidation states. Pd speciation and corresponding cataytic performance is a strong function of metal loading. Excellent activity is observed for the oxidative transamination of primary amines and acceptorless dehydrogenation of secondary amines to secondary imines using a low Pd loading (0.5 mol%), without the need for oxidants. N-heterocycles, such as indoline, 1,2,3,4-tetrahydroquinoline, and piperidine, are dehydrogenated to the corresponding aromatics with high yields. The relative yields of secondary imines are proportional to the calculated free energy of reaction, while yields for oxidative amination correlate with the electrophilicity of primary imine intermediates. Reversible amine dehydrogenation and imine hydrogenation determine the relative imine:amine selectivity. Poisoning tests evidence that Pd-LDHs operate heterogeneously, with negligible metal leaching; catalysts can be regenerated by acid dissolution and re-precipitation.</p> </div> <br>

Microwave-assisted Synthesis of Polymethoxychalcone Mannich Bases and Their Antiproliferative Activity

2019 ◽  
Vol 16 (2) ◽  
pp. 117-121 ◽  
Author(s):  
Peipei Han ◽  
Wenhua Zhou ◽  
Mingxia Chen ◽  
Qiuan Wang
Keyword(s):  
Cell Lines ◽  
Cancer Cell ◽  
Antiproliferative Activity ◽  
Mannich Base ◽  
Cancer Cell Lines ◽  
Secondary Amines ◽  
Conventional Heating ◽  
Microwave Assisted ◽  
Ic50 Values ◽  
Antiproliferative Activities

A series of eight polymethoxychalcone Mannich base derivatives 2a-2h was synthesized via the microwave-assisted Mannich reaction of natural product 2&#039;-hydroxy-3,4,4&#039;,5,6&#039;-pentamethoxychalcone (1) with various secondary amines and formaldehyde. Compared to conventional heating method (80&#176;C), the microwave-assisted method (700W, 65&#176;C) is efficient with short reaction time (0.5-1 h) and good yields (74-88%). The antiproliferative activities of eight Mannich base derivatives were evaluated in vitro on a panel of three human cancer cell lines (Hela, HCC1954 and SK-OV-3) by CCK-8 assay. The results showed that all of the Mannich base derivatives exhibited potential antiproliferative activities on tested cancer cell lines with the IC50 values of 9.13-48.51 &#181;M. Some active compounds exhibited more activity as compared to positive control cis-Platin. Among them, compound 2b revealed to have the strongest antiproliferative activity against all the three cancer cell lines with IC50 values ranging from 9.13 to 11.24 &#181;M.

The Development of Tyrosyl-DNA Phosphodyesterase 1 (TDP1) Inhibitors Based on the Amines Combining Aromatic/Heteroaromatic and Monoterpenoid Moieties

2019 ◽  
Vol 16 (5) ◽  
pp. 597-605 ◽  
Author(s):  
Evgenii Mozhaitsev ◽  
Evgenii Suslov ◽  
Yuliya Demidova ◽  
Dina Korchagina ◽  
Konstantin Volcho ◽  
...  
Keyword(s):  
Dna Repair ◽  
Tumor Cell ◽  
13C Nmr ◽  
Inhibitory Activity ◽  
Secondary Amines ◽  
Repair Enzyme ◽  
1H And 13C Nmr ◽  
Chemical Structures ◽  
Natural Substances ◽  
Micromolar Range

Background: Inhibition of the DNA repair enzyme, tyrosyl-DNA phosphodiesterase 1 (TDP1), may increase the efficacy of cancer drugs that cause damage to tumor cell DNA. Among the known TDP1 inhibitors, there are compounds containing moieties of natural substances, e.g., monoterpenoids. In this work, we synthesized several compounds containing aromatic/ heteroaromatic amines and monoterpenoid groups and assessed their TDP1 inhibition potential. Methods: Structures of all the synthesized compounds were confirmed by 1H and 13C NMR as well as HRMS. The TDP1 inhibitory activity of the amines was determined by real-time fluorescence oligonucleotide biosensor. Results: The synthesized secondary amines had TDP1 inhibitory activity IC50 in the range of 0.79-9.2 µM. The highest activity was found for (–)-myrtenal derivatives containing p-bromoaniline or m-(trifluoromethyl)aniline residue. Conclusion: We synthesized 22 secondary amines; of these, 17 amines are novel chemical structures. Many of the amines inhibit TDP1 activity in the low micromolar range. Therefore, these compounds are promising for further study of their antiproliferative activity in conjunction with DNA damaging drugs.

Novel coumarin containing dithiocarbamate derivatives as potent α-glucosidase inhibitors for management of type 2 diabetes

2020 ◽  
Vol 16 ◽  
Author(s):  
Marjan Mollazadeh ◽  
Maryam Mohammadi-Khanaposhtani ◽  
Yousef Valizadeh ◽  
Afsaneh Zonouzi ◽  
Mohammad Ali Faramarzi ◽  
...  
Keyword(s):  
Type 2 Diabetes ◽  
Kinetic Study ◽  
Active Site ◽  
Docking Study ◽  
Secondary Amines ◽  
Molecular Docking Study ◽  
Glucosidase Inhibitors ◽  
Dithiocarbamate Derivatives

Background: α-Glucosidase is a hydrolyze enzyme that plays a crucial role in degradation of carbohydrates and starch to glucose. Hence, α-glucosidase is an important target in the carbohydrate mediated diseases such as diabetes mellitus. Objective: In this study, novel coumarin containing dithiocarbamate derivatives 4a-n were synthesized and evaluated against α-glucosidase in vitro and in silico. Methods: These compounds were obtained of reaction between 4-(bromomethyl)-7-methoxy-2H-chromen-2-one 1, carbon disulfide 2, and primary or secondary amines 3a-n in the presence potassium hydroxide and ethanol at room temperature. In vitro α-glucosidase inhibition and kinetic study of these compounds were performed. Furthermore, docking study of the most potent compounds was also performed by Auto Dock Tools (version 1.5.6). Results: Obtained results showed that all the synthesized compounds exhibited prominent inhibitory activities (IC50 = 85.0 ± 4.0-566.6 ± 8.6 μM) in comparison to acarbose as standard inhibitor (IC50 = 750.0 ± 9.0 µM). Among them, secondary amine derivative 4d with pendant indole group was the most potent inhibitor. Enzyme kinetic study of the compound 4d revealed that this compound compete with substrate to connect to the active site of α-glucosidase and therefore is a competitive inhibitor. Also, molecular docking study predicted that this compound as well interacted with α-glucosidase active site pocket. Conclusion: Our results suggest that the coumarin-dithiocarbamate scaffold can be a promising lead structure for design potent α-glucosidase inhibitors for treatment of type 2 diabetes.

Pharmaceutico- Analytical Study of Abhra Sindoora

2018 ◽  
Vol 3 (4) ◽  
Author(s):  
Dr. Jyothi B. ◽  
Dr. M. V. Sobagin ◽  
Dr. M.C. Patil
Keyword(s):  
Analytical Study ◽  
Current Trend ◽  
Drug Analysis ◽  
Sem Analysis ◽  
Secondary Amines ◽  
Particle Analysis ◽  
Hexagonal Crystal ◽  
Xrd Study ◽  
Edxrf Analysis ◽  
Working Standards

Background: Abhra Sindoora[1] (ABS) is a unique Rasa Yoga with having more potent and indication in Tridoshahara, Swasa, Kasa etc. It is one of the important classical Kupipakva Rasayana containing Hingulotha Parada (purified mercury), Shuddha Gandhaka (purified sulfur) and Dhanyabhraka in 1:1:1 proportion. Aim: Pharmaceutico-Analytical study of Abhra Sindoora. Materials and Methods: Hingulotha Parada (purified mercury), Shuddha Gandhaka (purified sulfur) and Dhanyabhraka are used to prepare Kajjali and lavigated with Vatankura (leaf buds of Ficus bengalensis), Swarasa (juice) and Arka (Calotrapis procera) ksheera (milk). This Kajjali is processed by Kupipakva method. Results and Conclusion: The current trend in applied instrumental medical research encourages good medical practice, clinical and research based drug analysis. The main aim of analytical study is to find out working standards for the formulations and safe use of therapeutics. Abhra Sindoora was prepared in 48 hours with 28% yield. It was also characterized by using modern instrumental analysis like XRD, SEMEDX, EDXRF, FTIR and PARTICLE ANALYSIS. The SEM analysis evaluated that prepared Abhra Sindoora has particles in nanometers, least being 14.87nm. SEMEDX study confirmed the presence of C, O, Si, S, K, and HgM. XRD study confirmed the presence of Hg3.00S3.00 in hexagonal crystal system. The EDXRF analysis evaluated the presence of K, Ca, Ti, Mn, Fe, S, Br and Hg. FTIR analysis shows organic compounds with functional groups like secondary amines, Nitro, Carboxylic acids, Bromine, Esters, Alkines, and Iodides etc.

Reaction of arylmethylenemalonaldehydes with some nucleophiles

1987 ◽  
Vol 52 (11) ◽  
pp. 2699-2709 ◽  
Author(s):  
Dalimil Dvořák ◽  
Zdeněk Arnold
Keyword(s):  
Inorganic Anions ◽  
Secondary Amines ◽  
Tertiary Amines ◽  
Primary And Secondary Amines ◽  
Dipolar Structure

Reaction of arylmethylenemalonaldehydes with tributylphosphine and tertiary amines affords compounds of dipolar structure whereas reaction with primary and secondary amines leads to 1,4-addition products. Salts of nucleophilic inorganic anions add to arylmethylenemalonaldehydes under formation of salts of substituted malonaldehydes.

Synthesis of 2-amino-5,7-dimethyl-4-oxopyrido[3,4-e]-1,3-thiazines

1983 ◽  
Vol 48 (12) ◽  
pp. 3426-3432 ◽  
Author(s):  
Dušan Koščík ◽  
Pavol Kristian ◽  
Ondrej Forgáč
Keyword(s):  
Spectral Data ◽  
Chlorine Atom ◽  
Mass Spectra ◽  
High Reactivity ◽  
Secondary Amines ◽  
Dimroth Rearrangement ◽  
H Nmr ◽  
New Synthesis ◽  
C Nmr

New synthesis of pyrido[3,4-e]-1,3-thiazines consisting in reaction of 2,6-dimethyl-4-chloronicotinoyl isothiocyanate with primary or secondary amines, or with benzaldehyde phenylhydrazone, is described. High reactivity of the chlorine atom does not allow isolation of the corresponding thioureas, arising as intermediates, except in the case of the benzylamino derivative. Structure of the products was unequivocally confirmed by their spectral data (IR, UV, 1H NMR, 13C NMR and mass spectra). The synthesized derivatives do not undergo the Dimroth rearrangement.

Some 1-substitution derivatives of 4-aryl-2,3-dihalogeno-1-naphthols

1984 ◽  
Vol 49 (1) ◽  
pp. 110-121 ◽  
Author(s):  
Jiří Křepelka ◽  
Drahuše Vlčková ◽  
Milan Mělka
Keyword(s):  
Thionyl Chloride ◽  
Oxirane Ring ◽  
Secondary Amines ◽  
Two Phase ◽  
Lytic Effect ◽  
Primary And Secondary Amines ◽  
Phase Medium ◽  
Chloro Derivatives ◽  
Derivatives Of

Alkylation of derivatives of 4-aryl-1-naphthols (I-V) by 2,3-epoxypropyl chloride in methanolic sodium hydroxide gave epoxy derivatives VI, VIII, IX, XI and XII, apart from products of cleavage of the oxirane ring, VII and X. Analogous alkylation of compounds I, IV and V by 2-(N,N-diethylamino)ethyl chloride hydrochloride in a two-phase medium afforded basic ethers XIII to XV. The cleavage of the oxirane ring in compound VI by the action of primary and secondary amines, piperidine and substituted piperazines led to compounds XVI-XXIV. Reaction of thionyl chloride with compounds XXI, XXII and XXIV gave chloro derivatives XXV-XXVII.Exposure of compound XXII to 4-methylbenzenesulfonyl chloride produced compound XXVIII, retaining the secondary alcoholic group. In an antineoplastic screening in vivo none of the compounds prepared had an appreciable activity. Compound XVII, being an analogue of propranolol, was used in the test of isoproterenolic tachycardia, and showed a beta-lytic effect comparable with that of propranol.

New Substituted Difurylchalcones

1992 ◽  
Vol 57 (10) ◽  
pp. 2203-2207 ◽  
Author(s):  
Katarína Špirková ◽  
Štefan Stankovský
Keyword(s):  
Nmr Spectra ◽  
Knoevenagel Condensation ◽  
Secondary Amines ◽  
H Nmr ◽  
Nucleophilic Reactions

Preparation of 1-(5-substituted-2-furyl)-2-phenylsulfonyl-2-furoyl ethylenes (IIa-IId) using the Lehnert modification of Knoevenagel condensation, as well as substitution nucleophilic reactions of the 1-(5-bromo-2-furoyl)-2-phenylsulfonyl-2-furoyl derivative (IIa) with the corresponding phenolate, thiophenolate and secondary amines are described. IR, UV and 1H NMR spectra of final products are presented.

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