2-Arylmethylaminomethyl-5,6-dihydroxychromone derivatives with selective anti-HCV activity

Hye Ri Park; Kwang Su Park; Youhoon Chong

doi:10.1016/j.bmcl.2011.04.055

2-Arylmethylaminomethyl-5,6-dihydroxychromone derivatives with selective anti-HCV activity

Hye Ri Park
, Kwang Su Park
, Youhoon Chong

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

13 Scopus citations

Abstract

Anti-HCV activity of aryl diketoacid (ADK) has been characterized by its two pharmacophoric elements, α,β-diketo acid moiety and substituted aryl ring. In this study, as a part of our ongoing efforts to discover a novel anti-HCV compound mimicking the ADK scaffold, we designed 2- arylmethylaminomethyl-5,6-dihydroxychromone derivatives of which the dihydroxychromone moiety as well as the arylmethylaminomethyl substituent (R-PhCH ₂NHCH ₂-) were anticipated in exact match with the pharmacophore model of the ADK. The dihydroxychromone derivatives (3a-3u), thus prepared, showed biological activity in a substituent-dependent fashion, thereby leading to selective anti-HCV effect (EC ₅₀ = 2.0-14.0 μM, CC ₅₀ >100 μM) with the substituent groups such as Cl, Br, I, and Me specifically at the 3-position of the aromatic ring.

Original language	English
Pages (from-to)	3202-3205
Number of pages	4
Journal	Bioorganic and Medicinal Chemistry Letters
Volume	21
Issue number	11
DOIs	https://doi.org/10.1016/j.bmcl.2011.04.055
State	Published - 1 Jun 2011
Externally published	Yes

Keywords

2-Arylmethylaminomethyl-5,6-dihydroxychromone
ADK (aryl diketoacid)
Bioisostere
Hepatitis C virus (HCV)

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10.1016/j.bmcl.2011.04.055

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@article{9913f732309b4976ab6a64c627f5c173,

title = "2-Arylmethylaminomethyl-5,6-dihydroxychromone derivatives with selective anti-HCV activity",

abstract = "Anti-HCV activity of aryl diketoacid (ADK) has been characterized by its two pharmacophoric elements, α,β-diketo acid moiety and substituted aryl ring. In this study, as a part of our ongoing efforts to discover a novel anti-HCV compound mimicking the ADK scaffold, we designed 2- arylmethylaminomethyl-5,6-dihydroxychromone derivatives of which the dihydroxychromone moiety as well as the arylmethylaminomethyl substituent (R-PhCH 2NHCH 2-) were anticipated in exact match with the pharmacophore model of the ADK. The dihydroxychromone derivatives (3a-3u), thus prepared, showed biological activity in a substituent-dependent fashion, thereby leading to selective anti-HCV effect (EC 50 = 2.0-14.0 μM, CC 50 >100 μM) with the substituent groups such as Cl, Br, I, and Me specifically at the 3-position of the aromatic ring.",

keywords = "2-Arylmethylaminomethyl-5,6-dihydroxychromone, ADK (aryl diketoacid), Bioisostere, Hepatitis C virus (HCV)",

author = "Park, \{Hye Ri\} and Park, \{Kwang Su\} and Youhoon Chong",

note = "Funding Information: This research was supported by Basic Science Research Program through the National Research Foundation of Korea (NRF) funded by the Ministry of Education, Science and Technology ( 2010-0008260 ), and by Priority Research Centers Program through the National Research Foundation of Korea (NRF) funded by the Ministry of Education, Science and Technology ( 2009-0093824 ).",

year = "2011",

month = jun,

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doi = "10.1016/j.bmcl.2011.04.055",

language = "English",

volume = "21",

pages = "3202--3205",

journal = "Bioorganic and Medicinal Chemistry Letters",

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T1 - 2-Arylmethylaminomethyl-5,6-dihydroxychromone derivatives with selective anti-HCV activity

AU - Park, Hye Ri

AU - Park, Kwang Su

AU - Chong, Youhoon

N1 - Funding Information: This research was supported by Basic Science Research Program through the National Research Foundation of Korea (NRF) funded by the Ministry of Education, Science and Technology ( 2010-0008260 ), and by Priority Research Centers Program through the National Research Foundation of Korea (NRF) funded by the Ministry of Education, Science and Technology ( 2009-0093824 ).

PY - 2011/6/1

Y1 - 2011/6/1

N2 - Anti-HCV activity of aryl diketoacid (ADK) has been characterized by its two pharmacophoric elements, α,β-diketo acid moiety and substituted aryl ring. In this study, as a part of our ongoing efforts to discover a novel anti-HCV compound mimicking the ADK scaffold, we designed 2- arylmethylaminomethyl-5,6-dihydroxychromone derivatives of which the dihydroxychromone moiety as well as the arylmethylaminomethyl substituent (R-PhCH 2NHCH 2-) were anticipated in exact match with the pharmacophore model of the ADK. The dihydroxychromone derivatives (3a-3u), thus prepared, showed biological activity in a substituent-dependent fashion, thereby leading to selective anti-HCV effect (EC 50 = 2.0-14.0 μM, CC 50 >100 μM) with the substituent groups such as Cl, Br, I, and Me specifically at the 3-position of the aromatic ring.

AB - Anti-HCV activity of aryl diketoacid (ADK) has been characterized by its two pharmacophoric elements, α,β-diketo acid moiety and substituted aryl ring. In this study, as a part of our ongoing efforts to discover a novel anti-HCV compound mimicking the ADK scaffold, we designed 2- arylmethylaminomethyl-5,6-dihydroxychromone derivatives of which the dihydroxychromone moiety as well as the arylmethylaminomethyl substituent (R-PhCH 2NHCH 2-) were anticipated in exact match with the pharmacophore model of the ADK. The dihydroxychromone derivatives (3a-3u), thus prepared, showed biological activity in a substituent-dependent fashion, thereby leading to selective anti-HCV effect (EC 50 = 2.0-14.0 μM, CC 50 >100 μM) with the substituent groups such as Cl, Br, I, and Me specifically at the 3-position of the aromatic ring.

KW - 2-Arylmethylaminomethyl-5,6-dihydroxychromone

KW - ADK (aryl diketoacid)

KW - Bioisostere

KW - Hepatitis C virus (HCV)

UR - https://www.scopus.com/pages/publications/79956154206

U2 - 10.1016/j.bmcl.2011.04.055

DO - 10.1016/j.bmcl.2011.04.055

M3 - Article

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AN - SCOPUS:79956154206

SN - 0960-894X

VL - 21

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JO - Bioorganic and Medicinal Chemistry Letters

JF - Bioorganic and Medicinal Chemistry Letters

IS - 11

ER -

2-Arylmethylaminomethyl-5,6-dihydroxychromone derivatives with selective anti-HCV activity

Abstract

Keywords

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