Issues of Orthogonality and Stabilty: Synthesis of the Densely Functionalized Heterocyclic Ring System of the Antitumor Agents Azinomycins A and B

Synlett ◽  
1998 ◽  
Vol 1998 (10) ◽  
pp. 1031-1039 ◽  
Author(s):  
Robert S. Coleman
Keyword(s):  
Antitumor Agents ◽  
Heterocyclic Ring ◽  
Ring System

Tele-Substitution Reactions in the Synthesis of a Promising Class of Antimalarials

2020 ◽  
Author(s):  
Marat Korsik ◽  
Edwin Tse ◽  
David Smith ◽  
William Lewis ◽  
Peter J. Rutledge ◽  
...  
Keyword(s):  
Heterocyclic Ring ◽  
Ring System ◽  
Substitution Reactions ◽  
Laboratory Notebook ◽  
Polar Solvents ◽  
X Ray ◽  
X Ray Crystallography ◽  
The Core ◽  
Nmr Data

<p></p><p>We have discovered and studied a <i>tele</i>substitution reaction in a biologically important heterocyclic ring system. Conditions that favour the <i>tele</i>-substitution pathway were identified: the use of increased equivalents of the nucleophile or decreased equivalents of base, or the use of softer nucleophiles, less polar solvents and larger halogens on the electrophile. Using results from X-ray crystallography and isotope labelling experiments a mechanism for this unusual transformation is proposed. We focused on this triazolopyrazine as it is the core structure of the <i>in vivo </i>active anti-plasmodium compounds of Series 4 of the Open Source Malaria consortium.</p> <p> </p> <p>Archive of the electronic laboratory notebook with the description of all conducted experiments and raw NMR data could be accessed via following link <a href="https://ses.library.usyd.edu.au/handle/2123/21890">https://ses.library.usyd.edu.au/handle/2123/21890</a> . For navigation between entries of laboratory notebook please use file "Strings for compounds in the article.pdf" that works as a reference between article codes and notebook codes, also this file contain SMILES for these compounds. </p><br><p></p>

The Chemistry of Triazine Isomers: Structures, Reactions, Synthesis and Applications

2020 ◽  
Vol 20 ◽  
Author(s):  
Neelottama Kushwaha ◽  
C S Sharma
Keyword(s):  
Basic Property ◽  
Electrophilic Substitution ◽  
Antimicrobial Agents ◽  
Resonance Energy ◽  
Heterocyclic Ring ◽  
Ring System ◽  
Agricultural Fields ◽  
Substitution Reactions ◽  
Anti Cancer ◽  
Benzene Structure

: Triazine is the six-membered heterocyclic ring containing three nitrogen which replaces carbon-hydrogen unit in the benzene ring. Based on nitrogen position present in the ring system, it is categorized in three isomeric forms i.e.1, 2, 3-triazine (vicinal triazine), 1, 2, 4-triazine (asymmetrical triazine or isotriazine) and 1, 3, 5-triazine (symmetrical or s-triazine or cyanidine). Triazines have weakly basic property. Its isomers have much weaker resonance energy than benzene structure, so nucleophilic substitution reactions are more preferred than electrophilic substitution reactions. Triazine isomers and their derivatives are known to play important roles possessing various activities in medicinal and agricultural fields such as anti-cancer, antiviral, fungicidal, insecticidal, bactericidal, herbicidal, antimalarial and antimicrobial agents.

Resolving the Mystery of Ring Opening in the Synthesis of Benzo[d][1, 3]oxazin-4-one and Quinazolin-4(3H)-one

2019 ◽  
Vol 16 (11) ◽  
pp. 898-905
Author(s):  
Harun Patel ◽  
Rahul Pawara ◽  
Sanjay Surana
Keyword(s):  
Characteristic Feature ◽  
Ring Opening ◽  
Biological Activities ◽  
Heterocyclic Ring ◽  
Ring System ◽  
Time Saving ◽  
Fusion Strategy ◽  
Good Template ◽  
Lead Generation

Quinazoline is the six-membered heterocyclic ring system reported for its versatile biological activities. This characteristic feature of quinazoline makes it a good template for a lead generation library. Ring opening is one of the major concerns in the synthesis of quinazolin-4(3H)-one that results in diamide formation. Here, alternative fusion strategy is reported, which is a time-saving and costeffective method to overcome the ring opening problem associated with the synthesis of benzo[ d][1,3]oxazin-4-one and quinazolin-4(3H)-one.

Pyrido [2,3-d] thieno [3,2-b] [6H]thiopyran - ein neues heterocyclisches Ringsystem [1] / Pyrido [2,3-d]thieno[3,2-b] [6 H]thiopyran - a New Heterocyclic Ring System [1]

1979 ◽  
Vol 34 (11) ◽  
pp. 1573-1575 ◽  
Author(s):  
Klaus Beelitz ◽  
Klaus Praefcke ◽  
Salo Gronowitz
Keyword(s):  
Uv Irradiation ◽  
Benzene Solution ◽  
Heterocyclic Ring ◽  
Ring System ◽  
Spectroscopic Methods ◽  
System 1

Abstract UV irradiation of S-(3′-thienyl)2-chloro-thionicotinate (1) in benzene solution leads via dehydrohalogenation and cy clization in competition to α-cleavage to formation of thio-lactone 2 besides aldehyde 3 and disulphide 4. 2 contains a new heterocyclic ring system which has been confirmed by spectroscopic methods.

Triazole As Potent Anti-Cancer Agent- A Pharmacophoric Scaffold

2021 ◽  
Vol 17 ◽  
Author(s):  
Nidhi Kala ◽  
Kalpana Praveen Rahate
Keyword(s):  
Characteristic Feature ◽  
Biological Activities ◽  
Heterocyclic Ring ◽  
Ring System ◽  
Review Article ◽  
Current Review ◽  
Anti Cancer ◽  
Good Template ◽  
Cancer Agent

: Triazole is the main five-membered Nitrogen-containing basic heterocyclic ring system reported for their biological activities and compounds with multiple pharmacophores, which fetch together acquaintance of a target with sympathetic types of the molecule that might interact with the target. In addition, healthy, adaptable, and scalable chemistry must be employed to achieve the task. This characteristic feature of triazole would make a good template for a lead cohort library. The current review article focuses on recent advancements in triazole moiety as an anti-cancer agent with their mechanism pathways of synthesized analogues.

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