Highly Chemoselective Synthesis of Indolizidine Lactams by SmI2 -Induced Umpolung of the Amide Bond via Aminoketyl Radicals: Efficient Entry to Alkaloid Scaffolds

2016 ◽  
Vol 22 (34) ◽  
pp. 11949-11953 ◽  
Author(s):  
Shicheng Shi ◽  
Roger Lalancette ◽  
Roman Szostak ◽  
Michal Szostak
Keyword(s):  
Amide Bond ◽  
Chemoselective Synthesis

Hindered rotation around the amide bond in a series of derivatives of 2-acetamidothiophenes

1991 ◽  
Vol 88 ◽  
pp. 689-707 ◽  
Author(s):  
P Andriamadio ◽  
D Nicole ◽  
A Cartier ◽  
M Wierzbicki ◽  
G Kirsch
Keyword(s):  
Amide Bond ◽  
Hindered Rotation ◽  
Derivatives Of

Chemoselective Synthesis of Aminobenzylic Derivative of Mackinazolinone and its X-ray Investigations

2019 ◽  
Vol 9 (3) ◽  
pp. 109-114
Author(s):  
Nuritdinova R. R. ◽  
Elmuradov B. Zh. ◽  
Okmanov R. Ya. ◽  
Zakhidov K. A. ◽  
Tadjimukhamedov Kh.S.
Keyword(s):  
X Ray ◽  
Chemoselective Synthesis

Therapeutic Perspectives of Food Bioactive Peptides: A Mini Review

2019 ◽  
Vol 26 (9) ◽  
pp. 664-675
Author(s):  
Sulochana Priya
Keyword(s):  
Bioactive Peptides ◽  
Marine Organism ◽  
Biological Effects ◽  
Amide Bond ◽  
Therapeutic Effects ◽  
Specific Sequence ◽  
The Past ◽  
Cancer Immunity ◽  
Microbial Infections ◽  
Diverse Origin

Bioactive peptides are short chain of amino acids (usually 2-20) that are linked by amide bond in a specific sequence which have some biological effects in animals or humans. These can be of diverse origin like plant, animal, fish, microbe, marine organism or even synthetic. They are successfully used in the management of many diseases. In recent years increased attention has been raised for its effects and mechanism of action in various disease conditions like cancer, immunity, cardiovascular disease, hypertension, inflammation, diabetes, microbial infections etc. Bioactive peptides are more bioavailable and less allergenic when compared to total proteins. Food derived bioactive peptides have health benefits and its demand has increased tremendously over the past decade. This review gives a view on last two years research on potential bioactive peptides derived from food which have significant therapeutic effects.

Diethylphosphoryl-OxymaB (DEPO-B) as a Solid Coupling Reagent for Amide Bond Formation

2018 ◽  
Vol 16 (1) ◽  
pp. 30-33
Author(s):  
Ashish Kumar ◽  
Yahya E. Jad ◽  
Ayman El-Faham ◽  
Beatriz G. de la Torre ◽  
Fernando Albericio
Keyword(s):  
Bond Formation ◽  
Hydrolytic Stability ◽  
Solid Material ◽  
Amide Bond ◽  
Amide Bond Formation ◽  
Coupling Reagent

A new phosphonium based coupling reagent DEPO-B has been synthesized from 5- (hydroxyimino)-1,3-dimethylpyrimidine-2,4,6 (1H,3H,5H)-trione (Oxyma B) and diethyl chlorophosphate in presence of base. It is a solid material and the hydrolytic stability and solubility was evaluated for confirming its capability for usage in automated peptide synthesizer.

Copper Catalysts in the Synthesis of Five-membered N-polyheterocycles

2018 ◽  
Vol 15 (7) ◽  
pp. 940-971 ◽  
Author(s):  
Navjeet Kaur
Keyword(s):  
Transition Metal ◽  
Organic Synthesis ◽  
Copper Catalysts ◽  
Research Field ◽  
Chemoselective Synthesis ◽  
Specialized Equipment ◽  
Transition Metal Catalyzed ◽  
Synthetic Methodologies ◽  
Metal Catalyzed ◽  
Traditional Approaches

Background: Due to significant biological activity associated with N-, O- and S-heterocycles, a number of reports for their synthesis have appeared in recent decades. Traditional approaches require expensive or highly specialized equipment or would be of limited use to the synthetic organic chemist due to their highly inconvenient approaches. This review summarizes the applications of copper catalysts with the emphasis on their synthetic applications for nitrogen bearing polyheterocylces. In summary, this review article describes the synthesis of a number of five-membered poly heterocyclic rings. Objective: Nowadays new approaches that employ atom-economical and efficient pathway have been developed. The researchers are following natural models to design and synthesize heterocycles. The transition metal catalyzed protocols have attracted the attention as compared to other synthetic methodologies because they use easily available substrates to build multiple substituted complicated molecules directly under mild conditions. In organic synthesis, constituted by transition metal catalyzed coupling transformations are one of the most powerful and useful protocols. The N-heterocycles are synthesized by this convenient and useful tool. Conclusion: The efficient and chemoselective synthesis of heterocycles by this technique has appeared as an important tool. This review shows a highly dynamic research field and the employment of copper catalysts in organic synthesis. Several strategies have been pointed out in the past few years, to meet more sustainable, efficient and environmentally benign chemical products and procedures. The catalytic strategies have been the focus of intense research because they avoid the use of toxic reagents. Among these catalytic strategies, highly rewarding and an important method in heterocycles synthesis is metal catalyzed synthesis.

A Review of Amide Bond Formation in Microwave Organic Synthesis

2014 ◽  
Vol 11 (4) ◽  
pp. 592-604 ◽  
Author(s):  
Natalia Lukasik ◽  
Ewa Wagner-Wysiecka
Keyword(s):  
Organic Synthesis ◽  
Bond Formation ◽  
Amide Bond ◽  
Amide Bond Formation

scholarly journals Biotin-Containing Third Generation Glucoheptoamidated Polyamidoamine Dendrimer for 5-Aminolevulinic Acid Delivery System

2021 ◽  
Vol 22 (4) ◽  
pp. 1982 ◽  
Author(s):  
Aleksandra Kaczorowska ◽  
Małgorzata Malinga-Drozd ◽  
Wojciech Kałas ◽  
Marta Kopaczyńska ◽  
Stanisław Wołowiec ◽  
...  
Keyword(s):  
Reactive Oxygen Species ◽  
Aminolevulinic Acid ◽  
Reactive Oxygen ◽  
Pamam Dendrimer ◽  
Variable Number ◽  
Amide Bond ◽  
Oxygen Species ◽  
Nmr Spectrum ◽  
Guest Molecules ◽  
Amine Groups

Polyamidoamine PAMAM dendrimer generation 3 (G3) was modified by attachment of biotin via amide bond and glucoheptoamidated by addition of α-D-glucoheptono-1,4-lacton to obtain a series of conjugates with a variable number of biotin residues. The composition of conjugates was determined by detailed 1-D and 2-D NMR spectroscopy to reveal the number of biotin residues, which were 1, 2, 4, 6, or 8, while the number of glucoheptoamide residues substituted most of the remaining primary amine groups of PAMAM G3. The conjugates were then used as host molecules to encapsulate the 5-aminolevulinic acid. The solubility of 5-aminolevulinic acid increased twice in the presence of the 5-mM guest in water. The interaction between host and guest was accompanied by deprotonation of the carboxylic group of 5-aminolevulinic acid and proton transfer into internal ternary nitrogen atoms of the guest as evidenced by a characteristic chemical shift of resonances in the 1H NMR spectrum of associates. The guest molecules were most likely encapsulated inside inner shell voids of the host. The number of guest molecules depended on the number of biotin residues of the host, which was 15 for non-biotin-containing glucoheptoamidated G3 down to 6 for glucoheptoamidated G3 with 8 biotin residues on the host surface. The encapsulates were not cytotoxic against Caco-2 cells up to 200-µM concentration in the dark. All encapsulates were able to deliver 5-aminolevulinic acid to cells but aqueous encapsulates were more active in this regard. Simultaneously, the reactive oxygen species were detected by staining with H2DCFDA in Caco-2 cells incubated with encapsulates. The amount of PpIX was sufficient for induction of reactive oxygen species upon 30-s illumination with a 655-nm laser beam.

scholarly journals 4-[(2,4-Dichlorophenyl)carbamoyl]butanoic Acid

Molbank ◽  
10.3390/m1227 ◽  
2021 ◽  
Vol 2021 (2) ◽  
pp. M1227
Author(s):  
Bibi Hanifa ◽  
Muhammad Sirajuddin ◽  
Zafran Ullah ◽  
Sumera Mahboob ◽  
See Mun Lee ◽  
...  
Keyword(s):  
Torsion Angle ◽  
Acid Amide ◽  
Spectroscopic Characterization ◽  
Amide Bond ◽  
Amide Hydrogen ◽  
Butanoic Acid ◽  
X Ray ◽  
Amide Derivative

The synthesis and spectroscopic characterization of the glutaric acid-amide derivative, 2,4-Cl2C6H3N(H)C(=O)(CH2)3C(=O)OH (1), are described. The X-ray crystal structure determination of (1) shows the backbone of the molecule to be kinked about the methylene-C–N(amide) bond as seen in the C(p)–N–C(m)–C(m) torsion angle of −157.0(2)°; m = methylene and p = phenyl. An additional twist in the molecule is noted between the amide and phenyl groups as reflected in the C(m)–N–C(p)–C(p) torsion angle of 138.2(2)°. The most prominent feature of the molecular packing is the formation of supramolecular tapes assembled through carboxylic acid-O–H…O(carbonyl) and amide-N–H…O(amide) hydrogen bonding.

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