01312nas a2200241 4500008004100000022001400041245007900055210006900134260000800203300001400211490000700225520051100232100002500743700002100768700002700789700002100816700002400837700002800861700002800889700002400917700002100941856010800962 2025 eng d a0163-386400aPeganutonin A: computationally informed synthesis of its revised structure0 aPeganutonin A computationally informed synthesis of its revised  cAPR a1253-12580 v883 a

The structure of the recently isolated natural product peganutonin A was shown to be incorrect by analysis of the reported spectroscopic data, and therefore, the structure was reassigned utilizing computational methods. Subsequently, the computationally proposed reassignment was confirmed by total synthesis, which was achieved in seven steps from 6-methoxyindole. It is assumed that peganutonin A is not a natural product but an artifact arising from photooxidation of the alkaloid harmaline.

1 aSaranya, Sathya, Sai1 aChoudhury, Rahul1 aSupekar, Prathmesh, R.1 aBeduru, Srinivas1 aWilliams, Craig, M.1 aElyashberg, Mikhail, E.1 aKutateladze, Andrei, G.1 aBates, Roderick, W.1 aReddy, Srinivasa uhttps://library.ncl.res.in/content/peganutonin-computationally-informed-synthesis-its-revised-structure01666nas a2200313 4500008004100000022001400041245009900055210006900154260000800223300001400231490000700245520062800252653001900880653001900899653002000918653002800938653002600966653001500992100002501007700002101032700002201053700002701075700002001102700002901122700003201151700002501183700002101208856012301229 2025 eng d a1948-587500aReady access to benzodiazocines from tryptamines: a druggable scaffold toward antiviral agents0 aReady access to benzodiazocines from tryptamines a druggable sca cDEC a2362-23670 v163 a

Herein we report the first synthesis of the proposed structure of a benzodiazocine natural product, peganutonin A. Considering the druggable nature of benzodiazocine and its limited exploration in the field of medicinal chemistry, we generalized the approach and created a library of compounds useful for various biological activities. Key steps in present approach include tryptamine cyclization facilitated by tert-butyl hypochlorite and cleavage of the fused indole ring using ozonolysis. Preliminary screening of the synthesized compounds resulted in potent antiviral compounds against the SARS-CoV-2 virus.

10aBenzodiazocine10adrug discovery10aIndole cleavage10aLipinski's rule of Five10aSARS-CoV-2 inhibition10aTryptamine1 aSaranya, Sathya, Sai1 aChoudhury, Rahul1 aRoutholla, Ganesh1 aSupekar, Prathmesh, R.1 aR, Nandhakumaar1 aMartin, Alna, Kuriyickal1 aMuruganandham, Renuga, Devi1 aKumar, Bokara, Kiran1 aReddy, Srinivasa uhttps://library.ncl.res.in/content/ready-access-benzodiazocines-tryptamines-druggable-scaffold-toward-antiviral-agents