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Synthesis of Medium Ring Heterocyclic Compounds Using Carbohydrate Precursors

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Title Synthesis of Medium Ring Heterocyclic Compounds Using Carbohydrate Precursors
 
Creator Majhi, Tirtha Pada
 
Subject Chemistry
 
Description Heterocyclic compounds are worth our attention for many reasons; chief among them are their biological activities, and many drugs are heterocycles. Therefore, organic chemists have been making extensive efforts to produce these heterocyclic compounds by developing new and efficient synthetic transformations. Benzofused cyclic molecules incorporating at least one nitrogen atom in the structure are often referred to as “privileged structures” owing to their capability of binding to multiple receptors with high affinity.1 Benzofused seven- or eight membered cyclic amines, named as benzazepines or benzazocines respectively, exhibit important pharmacological properties and are currently under intense scrutiny for their physiological activity. For example, 1-benzazepine systems2 have shown significant antimicrobial and analgesic activity. 2-Benzazepines have been reported3 to be used as non peptide mimics for the well known tri-peptide sequence Arg-Gly-Asp (RGD), which interacts with αvβ3 integrin, a pivotal protein that plays a key role in cell-cell signaling and acts as its antagonist. 3-Benzazepines have inhibitory effect on reverse transcriptase.4 1-Benzazocine derivatives are described as CCR-5 antagonists and used against HIV infections and some other diseases also.5 These cyclic amine moieties are present in many pharmaceutically active naturally occurring molecules, for example: i) Galanthamine (1)6 isolated from Galanthus woronowii or Galanthus nivalis is one of the effective drugs for Alzheimer disease, the most common case of elderly dementia; ii) (+) –FR900482 (2)7 isolated from Streptomyces sandaensis and acts as an anti-tumor antibiotic;. iii) (-) Pancracine (3)8 isolated from Rhodophiala bifida of USA shows hypotensive and anticonvulsive activities. Besides lennoxamine (4),9 cephalotaxine (5),10 buflavine (6),11 lycoramine (7),12 chilenine (8),13 and montanine (9)14 are notable for their unique and synthetically challenging structures
 
Date 2007
 
Type Thesis
NonPeerReviewed
 
Format application/pdf
 
Identifier http://www.eprints.iicb.res.in/589/1/thesis_T_MAJHI.pdf
Majhi, Tirtha Pada (2007) Synthesis of Medium Ring Heterocyclic Compounds Using Carbohydrate Precursors. PhD thesis, Jadavpur University.
 
Relation http://www.eprints.iicb.res.in/589/