Microwave-assisted synthesis of zinc 5-(4-carboxyphenyl)-10,15,20-triphenylporphyrin and zinc 5-(4-carboxyphenyl)-10,15,20-triphenylchlorin

2015 ◽  
Vol 19 (04) ◽  
pp. 595-600 ◽  
Author(s):  
Rima Chouikrat ◽  
Aymeric Champion ◽  
Régis Vanderesse ◽  
Céline Frochot ◽  
Albert Moussaron
Keyword(s):  
Reaction Times ◽  
Microwave Assisted Synthesis ◽  
Spectroscopic Techniques ◽  
H Nmr ◽  
Microwave Assisted ◽  
Experimental Protocols ◽  
Time Of Reaction

The microwave-assisted synthesis of zinc 5-(4-carboxyphenyl)-10,15,20-triphenylporphyrin and zinc 5-(4-carboxyphenyl)-10,15,20-triphenylchlrorin are described and compared to classic conditions of synthesis in terms of time of reaction and yields obtained. The new experimental protocols are easy to implement required small amounts of reagents and solvents and lead to short reaction times. All compounds have been characterized by 1 H NMR, MS and spectroscopic techniques.

Microwave-assisted synthesis of porphyrins and metalloporphyrins: a rapid and efficient synthetic method

2007 ◽  
Vol 11 (02) ◽  
pp. 77-84 ◽  
Author(s):  
Bruno F. O. Nascimento ◽  
Marta Pineiro ◽  
António M. d'A. Rocha Gonsalves ◽  
Manuela Ramos Silva ◽  
Ana Matos Beja ◽  
...  
Keyword(s):  
Transition Metals ◽  
Reaction Times ◽  
Microwave Assisted Synthesis ◽  
Synthetic Method ◽  
One Pot ◽  
Microwave Assisted ◽  
Experimental Protocols ◽  
Porphyrin Core ◽  
High Yields

The effective 'one-pot' microwave-assisted synthesis of several substituted 5,10,15,20-tetraarylporphyrins is reported. The microwave-assisted insertion of five different transition metals into the 5,10,15,20-tetraphenylporphyrin, 5,10,15,20-tetrakis(4-chlorophenyl)porphyrin and 5,10,15,20-tetrakis(3-hydroxyphenyl)porphyrin core was also achieved with high yields. In addition to their simplicity, both these straightforward, experimental protocols were also characterized by extremely short reaction times and quite small quantities of solvents employed.

scholarly journals Microwave-Assisted Synthesis of (Piperidin-1-yl)quinolin-3-yl)methylene)hydrazinecarbothioamides as Potent Inhibitors of Cholinesterases: A Biochemical and In Silico Approach

Molecules ◽  
2021 ◽  
Vol 26 (3) ◽  
pp. 656
Author(s):  
Rubina Munir ◽  
Muhammad Zia-ur-Rehman ◽  
Shahzad Murtaza ◽  
Sumera Zaib ◽  
Noman Javid ◽  
...  
Keyword(s):  
Neurodegenerative Disorder ◽  
Critical Role ◽  
Public Health Problem ◽  
Microwave Assisted Synthesis ◽  
Major Public Health Problem ◽  
Spectroscopic Techniques ◽  
Dual Inhibitor ◽  
Microwave Assisted ◽  
Ic50 Values

Alzheimer’s disease (AD), a progressive neurodegenerative disorder, characterized by central cognitive dysfunction, memory loss, and intellectual decline poses a major public health problem affecting millions of people around the globe. Despite several clinically approved drugs and development of anti-Alzheimer’s heterocyclic structural leads, the treatment of AD requires safer hybrid therapeutics with characteristic structural and biochemical properties. In this endeavor, we herein report a microwave-assisted synthesis of a library of quinoline thiosemicarbazones endowed with a piperidine moiety, achieved via the condensation of 6/8-methyl-2-(piperidin-1-yl)quinoline-3-carbaldehydes and (un)substituted thiosemicarbazides. The target N-heterocyclic products were isolated in excellent yields. The structures of all the synthesized compounds were fully established using readily available spectroscopic techniques (FTIR, 1H- and 13C-NMR). Anti-Alzheimer potential of the synthesized heterocyclic compounds was evaluated using acetylcholinesterase (AChE) and butyrylcholinesterase (BChE) enzymes. The in vitro biochemical assay results revealed several compounds as potent inhibitors of both enzymes. Among them, five compounds exhibited IC50 values less than 20 μM. N-(3-chlorophenyl)-2-((8-methyl-2-(piperidin-1-yl)quinolin-3-yl)methylene)hydrazine carbothioamide emerged as the most potent dual inhibitor of AChE and BChE with IC50 values of 9.68 and 11.59 μM, respectively. Various informative structure–activity relationship (SAR) analyses were also concluded indicating the critical role of substitution pattern on the inhibitory efficacy of the tested derivatives. In vitro results were further validated through molecular docking analysis where interactive behavior of the potent inhibitors within the active pocket of enzymes was established. Quinoline thiosemicarbazones were also tested for their cytotoxicity using MTT assay against HepG2 cells. Among the 26 novel compounds, there were five cytotoxical and 18 showed proliferative properties.

scholarly journals Microwave-assisted synthesis and characterization of some optically active poly(ester-imide) thermoplastic elastomers

e-Polymers ◽  
2009 ◽  
Vol 9 (1) ◽  
Author(s):  
Saeed Zahmatkesh ◽  
Abdol Reza Hajipour
Keyword(s):  
Thermal Analyses ◽  
Specific Rotation ◽  
Thermoplastic Elastomers ◽  
Optically Active ◽  
Microwave Assisted Synthesis ◽  
H Nmr ◽  
Microwave Assisted ◽  
Diacid Chloride ◽  
Elemental Analyses

AbstractPyromellitic dianhydride (1) was reacted with L-leucine (2) to result in [N,N'-(pyromellitoyl)-bis-L-leucine diacid] (3). This compound (3) was converted to N,N'-(pyromellitoyl)-bis-L-leucine diacid chloride (4) by reaction with thionyl chloride. The microwave-assisted polycondensation of this diacid chloride (4) with polyethyleneglycol-diol (PEG-200) and/or three synthetic bisphenols furnish a series of new PEIs and Co-PEIs in a laboratory microwave oven (Milestone). The resulting polymers and copolymers have inherent viscosities in the range of 0.31- 0.53 dl g-1. These polymers are optically active, thermally stable and soluble in polar aprotic solvents such as DMF, DMSO, NMP, DMAc and sulfuric acid. All of the above polymers were fully characterized by IR spectroscopy, 1H NMR spectroscopy, elemental analyses, specific rotation and thermal analyses. Some structural characterizations and physical properties of these optically active PEIs and Co-PEIs are reported.

scholarly journals Green Chemistry Approach for Efficient Synthesis of Schiff Bases of Isatin Derivatives and Evaluation of Their Antibacterial Activities

2013 ◽  
Vol 2013 ◽  
pp. 1-5 ◽  
Author(s):  
Jnyanaranjan Panda ◽  
V. Jagannath Patro ◽  
Biswa Mohan Sahoo ◽  
Jitendriya Mishra
Keyword(s):  
Green Chemistry ◽  
Schiff Bases ◽  
Reaction Times ◽  
Antibacterial Activities ◽  
Primary Amines ◽  
Microwave Assisted Synthesis ◽  
Azomethine Group ◽  
Microwave Assisted ◽  
Isatin Derivatives

Microwave-assisted organic synthesis, a green chemistry approach, is nowadays widely used in the drug synthesis. Microwave-assisted synthesis improves both throughput and turnaround time for medicinal chemists by offering the benefits of drastically reduced reaction times, increased yields, and pure products. Schiff bases are the important class of organic compounds due to their flexibility, and structural diversities due to the presence of azomethine group which is helpful for elucidating the mechanism of transformation and rasemination reaction in biological system. This novel compound could also act as valuable ligands for the development of new chemical entities. In the present work, some Schiff bases of Isatin derivatives was synthesized using microwave heating method. Schiff base of Isatin were synthesized by condensation of the keto group of Isatin with different aromatic primary amines. They were characterized by means of spectral data and subsequently subjected to the in vitro antibacterial activities against gram positive and gram negative strains of microbes. It was observed that the compound with electron withdrawing substituents exhibited good antibacterial activities against almost all the micro organisms.

scholarly journals Microwave-Assisted Synthesis of Tetrahydrocarbazole Linked 1,2-Diazoles in Aqueous-Brønsted Acid Catalytic System

2017 ◽  
Vol 2017 ◽  
pp. 1-17 ◽  
Author(s):  
Zubi Sadiq ◽  
Erum Akbar Hussain ◽  
Narjis Naz ◽  
Ambreen Ghani ◽  
Kausar Yasmeen ◽  
...  
Keyword(s):  
Acetic Acid ◽  
Catalytic System ◽  
Multicomponent Reaction ◽  
Conventional Heating ◽  
Microwave Assisted Synthesis ◽  
Spectroscopic Techniques ◽  
Unsaturated Ketones ◽  
Microwave Assisted ◽  
Michael Type Addition

A new series of tetrahydrocarbazole coupled 1,2-diazoles 4/5/6(a–o) in moderate to excellent yield was synthesized successfully via multicomponent reaction approach by adopting Michael type-addition of hydrazines on in situ generated α,β-unsaturated ketones via aldol type strategy under synthetic microwave radiations and conventional heating. Structural confirmations of all the prepared compounds were achieved by spectroscopic techniques. The best results were achieved when equal amounts of water-acetic acid were used in microwave conditions in 4 minutes.

scholarly journals Microwave Assisted Synthesis of Six Member Ring Azaheterocycles and Their Antimycobacterial and Anticancer Evaluation

2001 ◽  
Vol 71 (3) ◽  
pp. 287-293 ◽  
Author(s):  
Cristina Al Matarneh ◽  
Catalina-Ionica Ciobanu ◽  
Violeta Mangalagiu ◽  
Gheorghita Zbancioc ◽  
Ramona Danac
Keyword(s):  
Breast Cancer ◽  
Prostate Cancer ◽  
Lung Cancer ◽  
Renal Cancer ◽  
Reaction Times ◽  
Antimycobacterial Activity ◽  
Microwave Assisted Synthesis ◽  
Thermal Heating ◽  
Microwave Assisted ◽  
Mw Irradiation

We report herein a comparative study concerning the influence of microwave (MW) irradiation comparative with conventional thermal heating (TH) in the reaction of six member ring azaheterocycles (derived from phenanthroline, quinoline, isoquinoline and phthalazine) with ethyl cyanoformate, and their anticancer and antimycobacterial activity. Under MW irradiation the reactions have some undeniable advantages: the reaction times decrease dramatically (from hours to minutes), the yields are higher, the reactions became selective in some cases (4,7-phenanthrolinium and phthalazinium ylides). The decreasing of reaction time+ from hours to minutes corroborated with the fact that in majority of cases the yield are higher and the selectivity is better, allow us to say that these reactions could be considered as eco-friendly. As far for biological activity, three of the compounds exhibited a significant antitumor activity against some cancer cell lines including prostate cancer, leukemia, renal cancer, lung cancer and breast cancer. The best potency in terms of growth inhibition of tumor cells (~45%) was shown by compound 4a against renal cancer A498 and ovarian cancer SK-OV-3 cells. The tested compounds have not shown any antimycobacterial activity against Mycobacterium tuberculosis.

scholarly journals Green, Microwave-Assisted Synthesis of O-Perbutyrylated-Alkyl-Glycosides

Proceedings ◽  
2019 ◽  
Vol 41 (1) ◽  
pp. 42
Author(s):  
Emmanuel Pérez-Escalante ◽  
Luis Guillermo González-Olivares ◽  
Araceli Castañeda-Ovando ◽  
Verónica Salazar-Pereda ◽  
John F. Trant ◽  
...  
Keyword(s):  
Lewis Acids ◽  
Model Compound ◽  
Traditional Approach ◽  
Reaction Times ◽  
Conventional Heating ◽  
Microwave Assisted Synthesis ◽  
Hydroxyl Groups ◽  
Alkyl Glycosides ◽  
Microwave Assisted ◽  
Synthetic Strategy

Chemical synthesis of carbohydrates is a challenging task. Several protection and deprotection steps of hydroxyl groups are required to ensure regioselective formation of the glycosidic bond. Usually, it is achieved through acylation, where conventional heating is combined with addition of Lewis acids as catalysts. This traditional approach has two drawbacks; it is time consuming and often catalysts are hazardous to the environment. An alternative route relies on application of microwaves and/or other Lewis acids with less or no toxicity. Such combination would reduce reaction times and offer a benign synthetic strategy to obtain peracylated compounds. The current work describes an efficient and environmentally mild synthesis of peracylated glycosides with potential application in enzymatic preparation of carbohydrates. Model compound O-perbutyrylated-phenyl-galactose was synthesized using imidazole as catalyst in the microwave-assisted process. The acylation protocol was optimized, and the target sugar was obtained at 50% yield after 1 h. In conclusion, the combination of imidazole and microwaves provides an excellent alternative to swiftly synthesize peracylated glycosides in a benign way.

Microwave-Assisted Synthesis of Azo Aromatic Diacyl Chlorides

2012 ◽  
Vol 524-527 ◽  
pp. 1702-1705
Author(s):  
Qing Chao Jia ◽  
Yan Jun Chen ◽  
Hong Min Hou
Keyword(s):  
Microwave Irradiation ◽  
Ultrasonic Irradiation ◽  
Reaction Times ◽  
Microwave Assisted Synthesis ◽  
Microwave Assisted

Six azo aromatic diacyl chlorides were synthesized under microwave irradiation. The method offers better yields in shorter reaction times compared to classical heating approaches and ultrasonic irradiation.

scholarly journals Microwave-Assisted Synthesis of Arylidene Acetophenones

2013 ◽  
Vol 2013 ◽  
pp. 1-5
Author(s):  
Sheauly Khatun ◽  
M. Z. H. Khan ◽  
Khodeza Khatun ◽  
M. A. Sattar
Keyword(s):  
Microwave Irradiation ◽  
Microwave Heating ◽  
Spectral Data ◽  
Condensation Reaction ◽  
Aromatic Aldehydes ◽  
Conventional Heating ◽  
Microwave Assisted Synthesis ◽  
Efficient Synthesis ◽  
H Nmr ◽  
Microwave Assisted

An efficient synthesis of arylidene acetophenones have been achieved by using the microwave heating in comparison to the conventional heating. In this work compound 1-phenyle-3-(4-droxyphenyle)-2-propen-1-one, 1-(4-chlorophenyle)-3-phenyle-2-propen-1-one, and 1-(4-chlorophenyle)-3-(4-hydroxyphenyle)-2-propen-1-one have been synthesized by the condensation reaction between aromatic aldehydes and substituted acetophenones under microwave irradiation. The compounds of aldehydes and acetophenones were used as benzaldehyde, parahydroxybenzaldehyde, acetophenone, and parachloroacetophenone. The result shows that the time taken for the reaction was reduced from the conventional 1-2 hours to 60–120 seconds. The yield of the compounds in the conventional heating was moderate while the highest yield of 90–98% was observed in MWI method. The structure of the compounds was characterized by their IR,1H-NMR spectral data.

scholarly journals MICROWAVE ASSISTED SYNTHESIS, A GREEN PROTOCOL FOR DEVELOPMENT OF NEW AND ADVANCED DRUG DELIVERY SYSTEMS, A REVIEW

2015 ◽  
Vol 3 (9SE) ◽  
pp. 1-4
Author(s):  
KalpanaVirendra Singh
Keyword(s):  
Reaction Times ◽  
Chemical Processes ◽  
Environmentally Benign ◽  
Reaction Pathways ◽  
Microwave Assisted Synthesis ◽  
Primary Concern ◽  
Green Protocol ◽  
Microwave Assisted ◽  
Chemistry Community ◽  
Complex Drug

Medicinal Chemistry community is considering new chemical processes, which are environmentally benign. Environmentally benign synthetic protocols have become the primary concern during complex drug discovery processes. Green chemistry is providing algorithms for protecting the environment, not by cleaning it, but by inventing new chemical processes that fuel the Economy and lifestyles, without causing any damage to the environment. Microwave assisted techniques has opened up new opportunities to the synthetic chemists in the form of new improved reaction pathways, that are not otherwise feasible. MAOS has reduced the reaction times from hours or days to minutes leading to efficient economic way for synthesis of large number of molecules. Present Review article attempts to focus on what is MAOS, how it is generated and works going on in this area.

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