Design, synthesis, and antiproliferative activity of new 1H-pyrrolo[3,2-c]pyridine derivatives against melanoma cell lines. Part 2

Myung Ho Jung, Mohammed I. El-Gamal, Mohammed S. Abdel-Maksoud, Taebo Sim, Kyung Ho Yoo, Chang Hyun Oh

Research output: Contribution to journalArticle

27 Citations (Scopus)

Abstract

A new series of diarylureas and diarylamides possessing 1H-pyrrolo[3,2-c]pyridine scaffold was designed and synthesized. Their in vitro antiproliferative activities against A375P human melanoma cell line and NCI-9 human melanoma cell line panel were tested. All the target compounds, except three amino derivatives 8g, h and 9h, demonstrated superior potencies against A375P to Sorafenib. In addition, compounds 8a and 9b-f demonstrated higher potencies than Vemurafenib against A375P. Compounds 8c and 9b were 7.50 and 454.90 times, respectively, more selective towards A375P melanoma cells over NIH3T3 fibroblasts. Furthermore, compounds 8d, e and 9a-d, f demonstrated very high potencies against the nine tested melanoma cell lines at the NCI. The bisamide derivatives 9a-c, f showed 2-digit nanomolar IC 50 values over different cell lines of the NCI-9 melanoma cell lines.

Original languageEnglish
Pages (from-to)4362-4367
Number of pages6
JournalBioorganic and Medicinal Chemistry Letters
Volume22
Issue number13
DOIs
Publication statusPublished - 2012 Jul 1

Fingerprint

Melanoma
Cells
Derivatives
Cell Line
Fibroblasts
Scaffolds
pyrrolo(3,2-c)pyridine

Keywords

  • A375P
  • Antiproliferative activity
  • Diarylamide
  • Diarylurea
  • Melanoma
  • Pyrrolo[3,2-c]pyridine

ASJC Scopus subject areas

  • Pharmaceutical Science
  • Drug Discovery
  • Organic Chemistry
  • Molecular Medicine
  • Molecular Biology
  • Clinical Biochemistry
  • Biochemistry

Cite this

Design, synthesis, and antiproliferative activity of new 1H-pyrrolo[3,2-c]pyridine derivatives against melanoma cell lines. Part 2. / Jung, Myung Ho; El-Gamal, Mohammed I.; Abdel-Maksoud, Mohammed S.; Sim, Taebo; Yoo, Kyung Ho; Oh, Chang Hyun.

In: Bioorganic and Medicinal Chemistry Letters, Vol. 22, No. 13, 01.07.2012, p. 4362-4367.

Research output: Contribution to journalArticle

Jung, Myung Ho ; El-Gamal, Mohammed I. ; Abdel-Maksoud, Mohammed S. ; Sim, Taebo ; Yoo, Kyung Ho ; Oh, Chang Hyun. / Design, synthesis, and antiproliferative activity of new 1H-pyrrolo[3,2-c]pyridine derivatives against melanoma cell lines. Part 2. In: Bioorganic and Medicinal Chemistry Letters. 2012 ; Vol. 22, No. 13. pp. 4362-4367.
@article{50c824082a524093b80763d7dad08d50,
title = "Design, synthesis, and antiproliferative activity of new 1H-pyrrolo[3,2-c]pyridine derivatives against melanoma cell lines. Part 2",
abstract = "A new series of diarylureas and diarylamides possessing 1H-pyrrolo[3,2-c]pyridine scaffold was designed and synthesized. Their in vitro antiproliferative activities against A375P human melanoma cell line and NCI-9 human melanoma cell line panel were tested. All the target compounds, except three amino derivatives 8g, h and 9h, demonstrated superior potencies against A375P to Sorafenib. In addition, compounds 8a and 9b-f demonstrated higher potencies than Vemurafenib against A375P. Compounds 8c and 9b were 7.50 and 454.90 times, respectively, more selective towards A375P melanoma cells over NIH3T3 fibroblasts. Furthermore, compounds 8d, e and 9a-d, f demonstrated very high potencies against the nine tested melanoma cell lines at the NCI. The bisamide derivatives 9a-c, f showed 2-digit nanomolar IC 50 values over different cell lines of the NCI-9 melanoma cell lines.",
keywords = "A375P, Antiproliferative activity, Diarylamide, Diarylurea, Melanoma, Pyrrolo[3,2-c]pyridine",
author = "Jung, {Myung Ho} and El-Gamal, {Mohammed I.} and Abdel-Maksoud, {Mohammed S.} and Taebo Sim and Yoo, {Kyung Ho} and Oh, {Chang Hyun}",
year = "2012",
month = "7",
day = "1",
doi = "10.1016/j.bmcl.2012.05.004",
language = "English",
volume = "22",
pages = "4362--4367",
journal = "Bioorganic and Medicinal Chemistry Letters",
issn = "0960-894X",
publisher = "Elsevier Limited",
number = "13",

}

TY - JOUR

T1 - Design, synthesis, and antiproliferative activity of new 1H-pyrrolo[3,2-c]pyridine derivatives against melanoma cell lines. Part 2

AU - Jung, Myung Ho

AU - El-Gamal, Mohammed I.

AU - Abdel-Maksoud, Mohammed S.

AU - Sim, Taebo

AU - Yoo, Kyung Ho

AU - Oh, Chang Hyun

PY - 2012/7/1

Y1 - 2012/7/1

N2 - A new series of diarylureas and diarylamides possessing 1H-pyrrolo[3,2-c]pyridine scaffold was designed and synthesized. Their in vitro antiproliferative activities against A375P human melanoma cell line and NCI-9 human melanoma cell line panel were tested. All the target compounds, except three amino derivatives 8g, h and 9h, demonstrated superior potencies against A375P to Sorafenib. In addition, compounds 8a and 9b-f demonstrated higher potencies than Vemurafenib against A375P. Compounds 8c and 9b were 7.50 and 454.90 times, respectively, more selective towards A375P melanoma cells over NIH3T3 fibroblasts. Furthermore, compounds 8d, e and 9a-d, f demonstrated very high potencies against the nine tested melanoma cell lines at the NCI. The bisamide derivatives 9a-c, f showed 2-digit nanomolar IC 50 values over different cell lines of the NCI-9 melanoma cell lines.

AB - A new series of diarylureas and diarylamides possessing 1H-pyrrolo[3,2-c]pyridine scaffold was designed and synthesized. Their in vitro antiproliferative activities against A375P human melanoma cell line and NCI-9 human melanoma cell line panel were tested. All the target compounds, except three amino derivatives 8g, h and 9h, demonstrated superior potencies against A375P to Sorafenib. In addition, compounds 8a and 9b-f demonstrated higher potencies than Vemurafenib against A375P. Compounds 8c and 9b were 7.50 and 454.90 times, respectively, more selective towards A375P melanoma cells over NIH3T3 fibroblasts. Furthermore, compounds 8d, e and 9a-d, f demonstrated very high potencies against the nine tested melanoma cell lines at the NCI. The bisamide derivatives 9a-c, f showed 2-digit nanomolar IC 50 values over different cell lines of the NCI-9 melanoma cell lines.

KW - A375P

KW - Antiproliferative activity

KW - Diarylamide

KW - Diarylurea

KW - Melanoma

KW - Pyrrolo[3,2-c]pyridine

UR - http://www.scopus.com/inward/record.url?scp=84862170286&partnerID=8YFLogxK

UR - http://www.scopus.com/inward/citedby.url?scp=84862170286&partnerID=8YFLogxK

U2 - 10.1016/j.bmcl.2012.05.004

DO - 10.1016/j.bmcl.2012.05.004

M3 - Article

C2 - 22647720

AN - SCOPUS:84862170286

VL - 22

SP - 4362

EP - 4367

JO - Bioorganic and Medicinal Chemistry Letters

JF - Bioorganic and Medicinal Chemistry Letters

SN - 0960-894X

IS - 13

ER -