Neural Anti-Inflammatory Natural Product Periconianone A: Total Synthesis and Biological Evaluation

Hanuman P. Kalmode; Suhag S. Patil; Kishor L. Handore; Paresh R. Athawale; Rambabu Dandela; Abhishek Kumar Verma; Anirban Basu; D. Srinivasa Reddy

doi:10.1002/ejoc.201900048

Neural Anti-Inflammatory Natural Product Periconianone A: Total Synthesis and Biological Evaluation

Hanuman P. Kalmode, Suhag S. Patil, Kishor L. Handore, Paresh R. Athawale, Rambabu Dandela, Abhishek Kumar Verma, Anirban Basu, D. Srinivasa Reddy

Research output: Contribution to journal › Article › peer-review

5 Scopus citations

Abstract

Total synthesis of periconianone A, an eremophilane-type sesquiterpenoid with impressive neural anti-inflammatory potential, has been accomplished. Diels–Alder/aldol strategy to construct tetrahydro-naphthalene-2,6-dione scaffold, allylic oxidation of dienone using DBU/O ₂ and postulated biomimetic aldol reaction to construct 6/6/6 tricyclic system are the highlights of the present synthesis. Furthermore, the synthesized (±)-periconianone A and two close analogs were tested for their neural anti-inflammatory activity using various assays. In the course of our study we found a structurally simplified analog is superior to (±)-periconianone A.

Original language	English
Pages (from-to)	2376-2381
Number of pages	6
Journal	European Journal of Organic Chemistry
Volume	2019
Issue number	13
DOIs	https://doi.org/10.1002/ejoc.201900048
State	Published - 9 Apr 2019
Externally published	Yes

Keywords

Allylic oxidation
Biological evaluation
Cytotoxicity
Diels–Alder/aldol
Periconianone A

ASJC Scopus subject areas

Physical and Theoretical Chemistry
Organic Chemistry

Access to Document

10.1002/ejoc.201900048

Cite this

@article{e13d87ec935b426293699db34293995b,

title = "Neural Anti-Inflammatory Natural Product Periconianone A: Total Synthesis and Biological Evaluation",

abstract = " Total synthesis of periconianone A, an eremophilane-type sesquiterpenoid with impressive neural anti-inflammatory potential, has been accomplished. Diels–Alder/aldol strategy to construct tetrahydro-naphthalene-2,6-dione scaffold, allylic oxidation of dienone using DBU/O 2 and postulated biomimetic aldol reaction to construct 6/6/6 tricyclic system are the highlights of the present synthesis. Furthermore, the synthesized (±)-periconianone A and two close analogs were tested for their neural anti-inflammatory activity using various assays. In the course of our study we found a structurally simplified analog is superior to (±)-periconianone A.",

keywords = "Allylic oxidation, Biological evaluation, Cytotoxicity, Diels–Alder/aldol, Periconianone A",

author = "Kalmode, {Hanuman P.} and Patil, {Suhag S.} and Handore, {Kishor L.} and Athawale, {Paresh R.} and Rambabu Dandela and Verma, {Abhishek Kumar} and Anirban Basu and Reddy, {D. Srinivasa}",

note = "Publisher Copyright: {\textcopyright} 2019 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim",

year = "2019",

month = apr,

day = "9",

doi = "10.1002/ejoc.201900048",

language = "English",

volume = "2019",

pages = "2376--2381",

journal = "European Journal of Organic Chemistry",

issn = "1434-193X",

publisher = "John Wiley and Sons Ltd",

number = "13",

}

TY - JOUR

T1 - Neural Anti-Inflammatory Natural Product Periconianone A

T2 - Total Synthesis and Biological Evaluation

AU - Kalmode, Hanuman P.

AU - Patil, Suhag S.

AU - Handore, Kishor L.

AU - Athawale, Paresh R.

AU - Dandela, Rambabu

AU - Verma, Abhishek Kumar

AU - Basu, Anirban

AU - Reddy, D. Srinivasa

PY - 2019/4/9

Y1 - 2019/4/9

N2 - Total synthesis of periconianone A, an eremophilane-type sesquiterpenoid with impressive neural anti-inflammatory potential, has been accomplished. Diels–Alder/aldol strategy to construct tetrahydro-naphthalene-2,6-dione scaffold, allylic oxidation of dienone using DBU/O 2 and postulated biomimetic aldol reaction to construct 6/6/6 tricyclic system are the highlights of the present synthesis. Furthermore, the synthesized (±)-periconianone A and two close analogs were tested for their neural anti-inflammatory activity using various assays. In the course of our study we found a structurally simplified analog is superior to (±)-periconianone A.

AB - Total synthesis of periconianone A, an eremophilane-type sesquiterpenoid with impressive neural anti-inflammatory potential, has been accomplished. Diels–Alder/aldol strategy to construct tetrahydro-naphthalene-2,6-dione scaffold, allylic oxidation of dienone using DBU/O 2 and postulated biomimetic aldol reaction to construct 6/6/6 tricyclic system are the highlights of the present synthesis. Furthermore, the synthesized (±)-periconianone A and two close analogs were tested for their neural anti-inflammatory activity using various assays. In the course of our study we found a structurally simplified analog is superior to (±)-periconianone A.

KW - Allylic oxidation

KW - Biological evaluation

KW - Cytotoxicity

KW - Diels–Alder/aldol

KW - Periconianone A

UR - http://www.scopus.com/inward/record.url?scp=85063213905&partnerID=8YFLogxK

U2 - 10.1002/ejoc.201900048

DO - 10.1002/ejoc.201900048

M3 - Article

AN - SCOPUS:85063213905

SN - 1434-193X

VL - 2019

SP - 2376

EP - 2381

JO - European Journal of Organic Chemistry

JF - European Journal of Organic Chemistry

IS - 13

ER -

Neural Anti-Inflammatory Natural Product Periconianone A: Total Synthesis and Biological Evaluation

Abstract

Keywords

ASJC Scopus subject areas

Access to Document

Other files and links

Fingerprint

Cite this