SSCU Seminar
Name: Dr. S. V. Eswaran
Affiliation: Ex: Head (Chemistry Department) and Dean (Academics), St Stephen’s College, Delhi
Title: Bicyclo [3. 3. 1] nonanes, ” Viswamayene” and “Fullarazirman”
Date & Time: Tuesday, 26th May 2026 at 04.00 p.m.
Venue: RBM Lecture Hall, Chemical Sciences Building
Abstract:
Bicyclo [3. 3. 1] nonanes are made up of two cyclohexane rings fused at positions 1, 3, which could lead to many different conformational possibilities, for example chair-chair, chair- boat, boat- boat, boat- chair conformational. These could interconvert into each other rapidly via the half chair, twist boat conformations. The energy barriers between these conformations could be small allowing for their rapid interconversion. NMR studies of these compounds pose many challenges.
We have prepared one of these in 3.5-kilogram quantity from Lignite (brown coal). Unlike the coal this compound is colorless, water soluble, fluorescent, ninhydrin positive and non-cytotoxic.
These results are more important as the use of lignite for power generation is being banned, as it leads to environmental pollution. Computational studies show that these compounds could serve as potential drugs for treating neuro degenerative diseases like Alzheimer’s, Parkinson’s, Dementia and Huntington’s diseases for which very few drugs are available.
“Viswamayene” is a molecule developed in our laboratory (named after Prof. M.A. Viswamitra, IISc, Bangalore) who determined its X-ray crystal structure (J. Heterocyclic Chem., 1996). NMR and MS studies provided early evidences for the unusual nature of this reaction. The reaction involves the formation of a ‘long lived’ singlet nitrene which does not flip to the triplet state and has a life span of 700 picoseconds (JPC 2012). This rare Nitrene-Carbene conversion has been established by us (JOC. 2014). Other papers on the subject include Tet. Lett. 2016, Tetrahedron 2017). The ”long lived’ nitrene allows for enhanced intermolecular reaction rates and has been used for making photoresists for microlithography and for making the microchip. The same concept has been successfully used for studying protein-protein interactions.
The reaction of one such nitrene with nano carbon materials [SWCNT, Fullerene (C60), and reduced Graphene oxide] followed by oxidation has been published by us (Chem. Select. 2019), J. Biomed. Nanotech. 2020 & 2022; Indian Patent 2023). One of these has been used with e-beam lithography for generating patterns at 50 and 90 nm, respectively which could lead to Nano devices.
The structure of “Fullarazirman” was established by MALDI– MS and ESR spectroscopy. However, NMR spectrum of this compound could not be recorded, possibly because the molecule undergoes very rapid rotation. Magnetic susceptibility studies of this compound have been done
but need much more discussion. These water-soluble nano carbon materials (Curr. Sci. 2017) are considered as a panacea for all diseases and also possibly could increase the lifespan. Is this true?
These water- soluble nano carbon materials show very high anti-cancer activity in vitro against a range of cancer cells including lung cancer, colorectal cancer, breast cancer and triple negative breast cancer with little or no toxicity. Recent in vivo results confirm these observations involving very high anti-cancer activity combined with no hepatotoxicity. Improved formulations and studies in large animals (dogs) will be followed by phase I trials in human beings.’ Could in vivo NMR/ MRI, ESR studies help in understanding the mechanism of action of these nano substances? Very few drugs are available for the treatment of Triple negative breast cancer and hence, our new compounds could qualify for “accelerated approval”.