scholarly journals Facile Synthesis of Propranolol and Novel Derivatives

2020 ◽  
Vol 2020 ◽  
pp. 1-10
Author(s):  
Vy Anh Tran ◽  
Nguyen Hai Tai Tran ◽  
Long Giang Bach ◽  
Trinh Duy Nguyen ◽  
Thi Thuong Nguyen ◽  
...  
Keyword(s):  
Water Solubility ◽  
Antihypertensive Drugs ◽  
Biological Activities ◽  
Pyridinium Chlorochromate ◽  
Butyl Bromide ◽  
H Nmr ◽  
Oxidation Reduction ◽  
High Yields ◽  
New Compounds ◽  
Layer Chromatography

Propranolol is one of the first medications of the beta-blocker used for antihypertensive drugs. This study reports the facile route for the synthesis of propranolol and its novel derivatives. Herein, propranolol synthesis proceeded from 1-naphthol and isopropylamine under mild and less toxic conditions. Novel propranolol derivatives were designed by reactions of propranolol with benzoyl chloride, pyridinium chlorochromate, and n-butyl bromide through esterification, oxidation reduction, and alkylation, respectively. The isolation and purity of compounds were conducted using column chromatography and thin-layer chromatography. Mass spectrometry and 1H-NMR spectroscopy were applied to identify new compounds structure. Propranolol derivatives from 2-chlorobenzoyl chloride (compound 3), 2-fluorobenzoyl chloride (compound 5), and especially acetic anhydride (compound 6) manifested high yields and significantly increased water solubility. Six semisynthetic propranolol derivatives promise to improve antioxidative and biological activities.

scholarly journals Recent Findings in Azaphilone Pigments

2021 ◽  
Vol 7 (7) ◽  
pp. 541
Author(s):  
Lúcia P. S. Pimenta ◽  
Dhionne C. Gomes ◽  
Patrícia G. Cardoso ◽  
Jacqueline A. Takahashi
Keyword(s):  
Water Solubility ◽  
Biological Activities ◽  
Low Cost ◽  
Scale Up ◽  
Structural Diversity ◽  
Downstream Processing ◽  
Global Market ◽  
Yield Improvement ◽  
Potential Applications ◽  
New Compounds

Filamentous fungi are known to biosynthesize an extraordinary range of azaphilones pigments with structural diversity and advantages over vegetal-derived colored natural products such agile and simple cultivation in the lab, acceptance of low-cost substrates, speed yield improvement, and ease of downstream processing. Modern genetic engineering allows industrial production, providing pigments with higher thermostability, water-solubility, and promising bioactivities combined with ecological functions. This review, covering the literature from 2020 onwards, focuses on the state-of-the-art of azaphilone dyes, the global market scenario, new compounds isolated in the period with respective biological activities, and biosynthetic pathways. Furthermore, we discussed the innovations of azaphilone cultivation and extraction techniques, as well as in yield improvement and scale-up. Potential applications in the food, cosmetic, pharmaceutical, and textile industries were also explored.

Synthesis and Biological Activities of Some Schiff's Bases from 4-amino-3-(3-hydroxybutyl)-1H-1, 2, 4-triazole-5-thione

2009 ◽  
Vol 2009 (4) ◽  
pp. 208-211 ◽  
Author(s):  
Jing Zhang ◽  
Lixue Zhang ◽  
Xinxiang Lei ◽  
Changfeng Zhou ◽  
Xiaodan Fu ◽  
...  
Keyword(s):  
Plant Growth ◽  
Elemental Analysis ◽  
Mass Concentration ◽  
Biological Activities ◽  
Schiff’S Bases ◽  
H Nmr ◽  
Schiff's Bases ◽  
High Yields ◽  
C Nmr ◽  
Growth Regulating Activity

Sixteen novel Schiff's bases have been synthesised in high yields from 4-amino-3-(3-hydroxybutyl)-1 H-1, 2, 4-triazole-5-thione. All the newly synthesised compounds have been characterised by elemental analysis, IR, 1H NMR, 13C NMR and MS. Plant growth-regulating activity tests showed that most compounds have remarkable effects on the growth of wheat and radish at a mass concentration of 50μg mL−1.

scholarly journals Synthesis, Structural Elucidation, and Antibacterial Evaluation of Some New Molecules Derived from Coumarin, 1,3,4-Oxadiazole, and Acetamide

2016 ◽  
Vol 2016 ◽  
pp. 1-10 ◽  
Author(s):  
Shahid Rasool ◽  
Aziz-ur-Rehman ◽  
Muhammad Athar Abbasi ◽  
Sabahat Zahra Siddiqui ◽  
Syed Adnan Ali Shah ◽  
...  
Keyword(s):  
Biological Activities ◽  
Basic Medium ◽  
Bacterial Strains ◽  
Alkyl Aryl ◽  
H Nmr ◽  
Intermolecular Cyclization ◽  
Biological Potential ◽  
Aryl Amines ◽  
Spectral Data Analysis ◽  
New Compounds

Because of the reported biological activities of coumarin, 1,3,4-oxadiazole, and acetamides, some new compounds incorporating these moieties were synthesized and evaluated for their biological potential against Gram-positive and Gram-negative bacteria. In the present work, 4-chlororesorcinol (1) and ethyl acetoacetate (2) were mixed in a strong acidic medium to synthesize 6-chloro-7-hydroxy-4-methyl-2-oxo-2H-chromene (3) which was subjected to the intermolecular cyclization after consecutive three steps to synthesize 5-[(6-chloro-4-methyl-2-oxo-2H-chromen-7-yl)oxy]methyl-1,3,4-oxadiazol-2-thiol (6). A series of acetamoyl electrophiles, 8a–o, were synthesized from aralkyl/alkyl/aryl amines, 7a–o, in an aqueous basic medium. The final compounds, 9a–o, were synthesized by the reaction of compounds 6 and 8a–o in DMF/NaH. The synthesized compounds were structurally elucidated by spectral data analysis of IR, 1H-NMR, and EIMS. The most of the synthesized compounds remained moderate to excellent antibacterial agents. The molecules, 9e, 9j, and 9k, were the most efficient ones against all the five bacterial strains taken into account.

scholarly journals Synthesis and Characterization of Novel 1,3-Thiazole and 2-Amino-1,3,4-Thiadiazole Derivatives

2014 ◽  
Vol 33 (2) ◽  
pp. 189 ◽  
Author(s):  
Mustafa Er ◽  
Ayşe Şahin ◽  
Hakan Tahtacı
Keyword(s):  
Biological Activities ◽  
High Yield ◽  
Synthesis And Characterization ◽  
Hantzsch Reaction ◽  
H Nmr ◽  
Thiadiazole Derivatives ◽  
High Yields ◽  
Mass Spectrometric Techniques ◽  
C Nmr

<p>Thiosemicarbazone derivatives <strong>3a–e</strong> were synthesized by the reaction of various aldehydes<strong> 1a–e</strong> with 4-methyl thiosemicarbazide <strong>2</strong> in 78% to 90% yield. Then, the thiazole moieties of the target materials <strong>5a–e</strong> were obtained in high yields (71–93%) using the Hantzsch reaction utilizing thiosemicarbazone derivatives <strong>3a–e</strong> with ethyl-2-chloroacetoacetic ester. The substituted nitrile derivatives <strong>7a–e</strong> were obtained in moderate to high yield (58–84%) from the reaction of compounds <strong>5a–e</strong> with chloroacetonitrile by the nucleophilic aliphatic substitution reaction in the presence of anhydrous potassium carbonate. Finally, substituted 2-amino-1,3,4-thiadiazole compounds <strong>9a–e</strong> were obtained in moderate to good yields (51–62%) from the reaction of thiosemicarbazide with substituted nitrile derivatives <strong>7a–e</strong>. As a result, compounds that all share a high disposition for biological activities were obtained. The structures of the newly synthesized compounds were confirmed by IR, <sup>1</sup>H NMR, <sup>13</sup>C NMR, elemental analysis, and mass spectrometric techniques.</p>

scholarly journals Synthesis of Daidzein Glycosides, α-Tocopherol Glycosides, Hesperetin Glycosides by Bioconversion and Their Potential for Anti-Allergic Functional-Foods and Cosmetics

Molecules ◽  
2019 ◽  
Vol 24 (16) ◽  
pp. 2975
Author(s):  
Yuya Fujitaka ◽  
Hiroki Hamada ◽  
Daisuke Uesugi ◽  
Atsuhito Kuboki ◽  
Kei Shimoda ◽  
...  
Keyword(s):  
Inhibitory Activity ◽  
Water Solubility ◽  
Biological Activities ◽  
Biological Effects ◽  
Physicochemical Stability ◽  
Peritoneal Mast Cells ◽  
Anti Cancer ◽  
New Compounds ◽  
Poor Absorption ◽  
Anti Inflammation

Daidzein is a common isoflavone, having multiple biological effects such as anti-inflammation, anti-allergy, and anti-aging. α-Tocopherol is the tocopherol isoform with the highest vitamin E activity including anti-allergic activity and anti-cancer activity. Hesperetin is a flavone, which shows potent anti-inflammatory effects. These compounds have shortcomings, i.e., water-insolubility and poor absorption after oral administration. The glycosylation of bioactive compounds can enhance their water-solubility, physicochemical stability, intestinal absorption, and biological half-life, and improve their bio- and pharmacological properties. They were transformed by cultured Nicotiana tabacum cells to 7-β-glucoside and 7-β-gentiobioside of daidzein, and 3′- and 7-β-glucosides, 3′,7-β-diglucoside, and 7-β-gentiobioside of hesperetin. Daidzein and α-tocopherol were glycosylated by galactosylation with β-glucosidase to give 4′- and 7-β-galactosides of daidzein, which were new compounds, and α-tocopherol 6-β-galactoside. These nine glycosides showed higher anti-allergic activity, i.e., inhibitory activity toward histamine release from rat peritoneal mast cells, than their respective aglycones. In addition, these glycosides showed higher tyrosinase inhibitory activity than the corresponding aglycones. Glycosylation of daidzein, α-tocopherol, and hesperetin greatly improved their biological activities.

scholarly journals Synthesis, Spectral Studies, Antibacterial and Antifungal Activity of 2"-Methoxy-4"-[2 -(4'-Chlorophenyl)-6-Methyl Imidazo[1, 2-a]Pyridin-3-yl]-6"-Aryl Nicotinonitrile

2015 ◽  
Vol 49 ◽  
pp. 155-160
Author(s):  
V.V. Bhuva ◽  
V.N. Bhadani ◽  
H.D. Purohit ◽  
Dipak M. Purohit
Keyword(s):  
Biological Activities ◽  
Industrial Applications ◽  
Spectral Studies ◽  
Moderate Activity ◽  
Industrial Chemistry ◽  
Mass Spectral ◽  
H Nmr ◽  
Bacteria And Fungi ◽  
Antibacterial And Antifungal ◽  
Layer Chromatography

Pyridine nucleus plays an important role in medicine, agriculture and industrial chemistry. With a view of biological activities and variety of industrial applications, some new 2" – methoxy - 4" - [2 - ( 4' -chlorophenyl)-6-methyl imidazo [1, 2-a] pyridin-3-yl]-6"-aryl nicotinonitrile( 4a-4l ) has been synthesized. The products have been assayed for their biological activity against Gram +ve, Gram –ve bacteria and fungi. Some of the products showed moderate activity in concentration 50µg/ml. The structures of the products have been elucidated by IR, 1H-NMR, Mass spectral data, elemental analysis and thin layer chromatography.

Synthesis and 1H NMR Complexation Study of Thiacalix[4]arene Tetraacetates

2000 ◽  
Vol 65 (5) ◽  
pp. 757-771 ◽  
Author(s):  
Pavel Lhoták ◽  
Václav Šťastný ◽  
Petra Zlatušková ◽  
Ivan Stibor ◽  
Veronika Michlová ◽  
...  
Keyword(s):  
1H Nmr ◽  
Ethyl Bromoacetate ◽  
H Nmr ◽  
Partial Cone ◽  
High Yields ◽  
New Compounds ◽  
Complexation Ability

Alkylation of thiacalix[4]arenes with ethyl bromoacetate led to high yields (≈60%) of corresponding tetraacetates in various conformations (cone, partial cone, 1,3-alternate) depending strictly on the carbonate (Na, K, Cs) used for the reaction. The complexation ability of new compounds was studied by 1H NMR.

scholarly journals Synthesis, Spectral Studies Antibacterial and Antifungal Activity of 2"-Amino-4"-[2 -(4'-Chlorophenyl)-6-Methyl Imidazo[1, 2-a]Pyridin-3-yl]-6"-Aryl Nicotinonitrile

2015 ◽  
Vol 49 ◽  
pp. 161-166
Author(s):  
V.V. Bhuva ◽  
V.N. Bhadani ◽  
H.D. Purohit ◽  
Dipak M. Purohit
Keyword(s):  
Biological Activities ◽  
Industrial Applications ◽  
Spectral Studies ◽  
Moderate Activity ◽  
Industrial Chemistry ◽  
Mass Spectral ◽  
H Nmr ◽  
Bacteria And Fungi ◽  
Antibacterial And Antifungal ◽  
Layer Chromatography

Pyridine nucleus plays an important role in medicine, agriculture and industrial chemistry. With a view of biological activities and variety of industrial applications, some new 2" – amino - 4" - [2 - (4' -chlorophenyl)-6-methyl imidazo [1, 2-a] pyridin-3-yl]-6"-aryl nicotinonitriles ( 4a-4l ) have been synthesized. The products have been assayed for their biological activity against Gram +ve, Gram –ve bacteria and fungi. Some of the products showed moderate activity in concentration 50μg/ml. The structures of the products have been elucidated by IR, 1H-NMR, Mass spectral data, elemental analysis and thin layer chromatography.

Design, Synthesis and Biological Evaluation of of Novel Anticancer Agent tert-butyl 1-phenyl-3,4-dihydro-1H-pyrido[3,4-b]indole-2(9H)-carboxylate

2013 ◽  
Vol 781-784 ◽  
pp. 2211-2214
Author(s):  
Biao Shi ◽  
Yi Qian Wang ◽  
Yao Yang ◽  
Peng Yu ◽  
Kui Lu
Keyword(s):  
Biological Activities ◽  
Biological Properties ◽  
Biological Evaluation ◽  
Nmr Spectrum ◽  
Design Synthesis ◽  
H Nmr ◽  
Growth Inhibitory ◽  
Wide Range ◽  
New Compounds ◽  
Synthesis And Biological Evaluation

Indole and its derivatives extensively exist in nature, which showed a wide range of biological activities. Recently, there is a growing tendency to develop some new methods for the synthesis of novel indole derivatives and to study their biological properties. In this paper, we would like to report the design, synthesis and biological evaluation of a novel series of tricyclic indoles by employing Pictet-Spengler reaction as key step. All the target compounds were synthesized in four steps in 68-78% overall yield, which were characterized by 1H-NMR spectrum. All this new compounds were tested in an MTT assay on HepG2 and K562 and HT-29. Two of them showed tumor cell growth inhibitory good activity.

scholarly journals Novel Aryl Ether Derivatives as Antiinflammatory and Analgesics

2011 ◽  
Vol 8 (3) ◽  
pp. 1401-1407
Author(s):  
P. Rashmi ◽  
Gopal Krishna Rao ◽  
Kshama Devi ◽  
B. G. Shivananda ◽  
G. R. Swetha ◽  
...  
Keyword(s):  
Analgesic Activity ◽  
Mass Spectra ◽  
Biological Activities ◽  
Aryl Ether ◽  
H Nmr ◽  
Diaryl Ether ◽  
Wide Range ◽  
Aryl Ethers ◽  
New Compounds

The diaryl ether moieties have attracted considerable attention of medicinal chemists as they are endowed with a wide range of diverse biological activities. The present study involves synthesis, characterization of some new aryl ethers and evaluation of their antiinflammatory and analgesic activity. A series of new aryl ether derivatives[4(a-h), 5]were prepared by Ullmann’s ether condensation. The structures of new compounds are supported by their IR,1H NMR and Mass spectra. The new derivatives were evaluated for their antiinflammatory and analgesic activity. Among the tested, compound3has shown better antiinflammatory and analgesic activity.

Sign in / Sign up

Export Citation Format

Share Document