Abstract
Benzimidazoles and quinoxalinones are present in the core of many pharmacologically relevant compounds. Several combinatorial methods have been developed to attach ring systems to both scaffolds for derivatization at select positions. Herein, we describe the development of novel constrained heterocyclic compounds attached to the N1 position of both benzimidazole and quinoxalinone scaffolds. Utilizing robust post-Ugi cyclization methods, including the Ugi-deprotection-cyclization (UDC) methodology, allows for efficient access to a new area of chemical space. Additionally, molecular modeling and in cellulo screening was employed to therapeutically validate the compounds formed with this method.
| Original language | English (US) |
|---|---|
| Pages (from-to) | 11821-11825 |
| Number of pages | 5 |
| Journal | ChemistrySelect |
| Volume | 2 |
| Issue number | 35 |
| DOIs | |
| State | Published - Jan 1 2017 |
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Keywords
- Heterocycle Formation
- MDM2/MDMX
- Multicomponent Reaction
- Post-Ugi Modifications
- Ugi Condensation
ASJC Scopus subject areas
- Chemistry(all)
Cite this
Synthesis of Constrained Heterocycles Employing Two Post-Ugi Cyclization Methods for Rapid Library Generation with In Cellulo Activity. / McConnell, Nicholas; Xu, Zhigang; Kumarasamy, Vishnu; Sun, Daekyu; Frett, Brendan; Li, Hong Yu.
In: ChemistrySelect, Vol. 2, No. 35, 01.01.2017, p. 11821-11825.Research output: Contribution to journal › Article
}
TY - JOUR
T1 - Synthesis of Constrained Heterocycles Employing Two Post-Ugi Cyclization Methods for Rapid Library Generation with In Cellulo Activity
AU - McConnell, Nicholas
AU - Xu, Zhigang
AU - Kumarasamy, Vishnu
AU - Sun, Daekyu
AU - Frett, Brendan
AU - Li, Hong Yu
PY - 2017/1/1
Y1 - 2017/1/1
N2 - Benzimidazoles and quinoxalinones are present in the core of many pharmacologically relevant compounds. Several combinatorial methods have been developed to attach ring systems to both scaffolds for derivatization at select positions. Herein, we describe the development of novel constrained heterocyclic compounds attached to the N1 position of both benzimidazole and quinoxalinone scaffolds. Utilizing robust post-Ugi cyclization methods, including the Ugi-deprotection-cyclization (UDC) methodology, allows for efficient access to a new area of chemical space. Additionally, molecular modeling and in cellulo screening was employed to therapeutically validate the compounds formed with this method.
AB - Benzimidazoles and quinoxalinones are present in the core of many pharmacologically relevant compounds. Several combinatorial methods have been developed to attach ring systems to both scaffolds for derivatization at select positions. Herein, we describe the development of novel constrained heterocyclic compounds attached to the N1 position of both benzimidazole and quinoxalinone scaffolds. Utilizing robust post-Ugi cyclization methods, including the Ugi-deprotection-cyclization (UDC) methodology, allows for efficient access to a new area of chemical space. Additionally, molecular modeling and in cellulo screening was employed to therapeutically validate the compounds formed with this method.
KW - Heterocycle Formation
KW - MDM2/MDMX
KW - Multicomponent Reaction
KW - Post-Ugi Modifications
KW - Ugi Condensation
UR - http://www.scopus.com/inward/record.url?scp=85041829220&partnerID=8YFLogxK
UR - http://www.scopus.com/inward/citedby.url?scp=85041829220&partnerID=8YFLogxK
U2 - 10.1002/slct.201702179
DO - 10.1002/slct.201702179
M3 - Article
VL - 2
SP - 11821
EP - 11825
JO - ChemistrySelect
JF - ChemistrySelect
SN - 2365-6549
IS - 35
ER -