Synthesis and structural optimization of multiple H-bonding region of diarylalkyl (thio)amides as novel TRPV1 antagonists

Fu Nan Li; Nam Jung Kim; Dong Jo Chang; Jaebong Jang; Hannah Jang; Jong Wha Jung; Kyung Hoon Min; Yeon Su Jeong; Sun Young Kim; Young Ho Park; Hee Doo Kim; Hyeung Geun Park; Young Ger Suh

doi:10.1016/j.bmc.2009.10.043

Synthesis and structural optimization of multiple H-bonding region of diarylalkyl (thio)amides as novel TRPV1 antagonists

Fu Nan Li, Nam Jung Kim, Dong Jo Chang, Jaebong Jang, Hannah Jang, Jong Wha Jung, Kyung Hoon Min, Yeon Su Jeong, Sun Young Kim, Young Ho Park, Hee Doo Kim, Hyeung Geun Park, Young Ger Suh

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6 Scopus citations

Abstract

Structural optimization of multiple H-bonding region and structure-activity relationship of diarylalkyl amides/thioamides as novel TRPV1 antagonists are described. In particular, we identified amide 34o and thioamides 35o and 35r, of which antagonistic activities were highly enhanced by an incorporation of cyano or vinyl-substituent to the multiple H-bonding region. They exhibited potent ⁴⁵Ca²⁺ uptake inhibitions in rat DRG neuron with IC₅₀s of 25, 32 and 28 nM, respectively.

Original language	English
Pages (from-to)	8149-8160
Number of pages	12
Journal	Bioorganic and Medicinal Chemistry
Volume	17
Issue number	24
DOIs	https://doi.org/10.1016/j.bmc.2009.10.043
State	Published - 15 Dec 2009

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Li, F. N., Kim, N. J., Chang, D. J., Jang, J., Jang, H., Jung, J. W., Min, K. H., Jeong, Y. S., Kim, S. Y., Park, Y. H., Kim, H. D., Park, H. G., & Suh, Y. G. (2009). Synthesis and structural optimization of multiple H-bonding region of diarylalkyl (thio)amides as novel TRPV1 antagonists. Bioorganic and Medicinal Chemistry, 17(24), 8149-8160. https://doi.org/10.1016/j.bmc.2009.10.043

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abstract = "Structural optimization of multiple H-bonding region and structure-activity relationship of diarylalkyl amides/thioamides as novel TRPV1 antagonists are described. In particular, we identified amide 34o and thioamides 35o and 35r, of which antagonistic activities were highly enhanced by an incorporation of cyano or vinyl-substituent to the multiple H-bonding region. They exhibited potent 45Ca2+ uptake inhibitions in rat DRG neuron with IC50s of 25, 32 and 28 nM, respectively.",

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AU - Li, Fu Nan

AU - Kim, Nam Jung

AU - Chang, Dong Jo

AU - Jang, Jaebong

AU - Jang, Hannah

AU - Jung, Jong Wha

AU - Min, Kyung Hoon

AU - Jeong, Yeon Su

AU - Kim, Sun Young

AU - Park, Young Ho

AU - Kim, Hee Doo

AU - Park, Hyeung Geun

AU - Suh, Young Ger

PY - 2009/12/15

Y1 - 2009/12/15

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AB - Structural optimization of multiple H-bonding region and structure-activity relationship of diarylalkyl amides/thioamides as novel TRPV1 antagonists are described. In particular, we identified amide 34o and thioamides 35o and 35r, of which antagonistic activities were highly enhanced by an incorporation of cyano or vinyl-substituent to the multiple H-bonding region. They exhibited potent 45Ca2+ uptake inhibitions in rat DRG neuron with IC50s of 25, 32 and 28 nM, respectively.

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JO - Bioorganic and Medicinal Chemistry

JF - Bioorganic and Medicinal Chemistry

IS - 24

ER -

Synthesis and structural optimization of multiple H-bonding region of diarylalkyl (thio)amides as novel TRPV1 antagonists

Abstract

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