DDD-016

DDD-016 is a novel pentacyclic compound initially designed and synthesized as a potential atypical antipsychotic, with its receptor binding affinities screened across a broad panel of over 80 central nervous system and other receptors.[1] As part of a series of investigational compounds—which also includes DDD-024, DDD-025, and DDD-029[2] stands out for its proposed anti-psychotic activity, believed to be mediated through dual serotonin 5-HT2A and dopamine D2 receptor antagonism.[3]

## Synthesis

DDD-016 synthesis

A Goldberg reaction between 2-aminothiophenol [137-07-5] (1) and 2-bromobenzyl bromide [3433-80-5] (2) gives 5,11-Dihydrodibenzo[b,e][1,4]thiazepine, [3048-78-0] (3). Nitrosylation with nitrous acid gives (4). This is then reduced to the amino group. Condensation with 1-Methyl-4-piperidone [1445-73-4] gives (5). Fischer indole synthesis completes the synthesis.

{Note that the Goldberg reaction is being replaced by the Hartwig amination.}

## See also

Rajagopalan also invented a highly novel antidepressant earlier in his career:[4]

## References

1. ↑ "The synthesis and receptor binding affinities of DDD-016, a novel, potential, atypical antipsychotic". MedChemComm 3 (5): 580. 2012. doi:10.1039/c2md00311b.
2. ↑ "The synthesis and comparative receptor binding affinities of novel, isomeric pyridoindolobenzazepine scaffolds". Bioorganic & Medicinal Chemistry Letters 24 (2): 576–579. January 2014. doi:10.1016/j.bmcl.2013.12.024. PMID 24365159.
3. ↑ "DDD-028: a potent potential non-opioid, non-cannabinoid analgesic for neuropathic and inflammatory pain". Bioorganic & Medicinal Chemistry Letters 24 (14): 3088–3091. July 2014. doi:10.1016/j.bmcl.2014.05.016. PMID 24863744.
4. ↑ "Synthetic CNS agents. 1. (+/-)-1,2,3,4,4a,5,10,10a-Octahydro-5,10[1',2'] -benzenobenz[g]isoquinoline hydrochloride. A new, highly potent, potential antidepressant". Journal of Medicinal Chemistry 27 (8): 946–947. August 1984. doi:10.1021/jm00374a002. PMID 6747994.

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