Small molecule inhibitors of anthrax lethal factor toxin

JD Williams, AR Khan, SC Cardinale, MM Butler…

Index: Williams, John D.; Khan, Atiyya R.; Cardinale, Steven C.; Butler, Michelle M.; Bowlin, Terry L.; Peet, Norton P. Bioorganic and Medicinal Chemistry, 2014 , vol. 22, # 1 p. 419 - 434

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Citation Number: 2

Abstract

Abstract This manuscript describes the preparation of new small molecule inhibitors of Bacillus anthracis lethal factor. Our starting point was the symmetrical, bis-quinolinyl compound 1 (NSC 12155). Optimization of one half of this molecule led to new LF inhibitors that were desymmetrized to afford more drug-like compounds.

 Related Synthetic Route
N/A Structure

6236-69-7

N/A

~96%

METHYL 3-(2-HYDROXYPHENYL)PROPIONATE Structure

20349-89-7

METHYL 3-(2-HYD...

Structure

1528735-41-2

trifluoroacetic acid Structure

76-05-1

trifluoroacetic acid

~%

N-(4-amino-2-methyl-quinolin-6-yl)-2-phenyl-acetamide Structure

7511-77-5

N-(4-amino-2-me...

4-Nitroaniline Structure

100-01-6

4-Nitroaniline

~%

N-(4-amino-2-methyl-quinolin-6-yl)-2-phenyl-acetamide Structure

7511-77-5

N-(4-amino-2-me...

2-methyl-6-nitro-1H-quinolin-4-one Structure

112219-43-9

2-methyl-6-nitr...

~%

N-(4-amino-2-methyl-quinolin-6-yl)-2-phenyl-acetamide Structure

7511-77-5

N-(4-amino-2-me...

4-azido-2-methyl-6-nitroquinoline Structure

1528735-22-9

4-azido-2-methy...

~%

N-(4-amino-2-methyl-quinolin-6-yl)-2-phenyl-acetamide Structure

7511-77-5

N-(4-amino-2-me...

4-chloro-2-methyl-6-nitroquinoline Structure

1207-81-4

4-chloro-2-meth...

~%

N-(4-amino-2-methyl-quinolin-6-yl)-2-phenyl-acetamide Structure

7511-77-5

N-(4-amino-2-me...

2-Methyl-4-aMino-6-nitroquinoline Structure

99185-71-4

2-Methyl-4-aMin...

~%

N-(4-amino-2-methyl-quinolin-6-yl)-2-phenyl-acetamide Structure

7511-77-5

N-(4-amino-2-me...

4-[di(N-Boc)amino]-2-methyl-6-nitroquinoline Structure

1528735-23-0

4-[di(N-Boc)ami...

~%

N-(4-amino-2-methyl-quinolin-6-yl)-2-phenyl-acetamide Structure

7511-77-5

N-(4-amino-2-me...

6-amino-4-[di(N-Boc)amino]-2-methylquinoline Structure

1528735-24-1

6-amino-4-[di(N...

~%

N-(4-amino-2-methyl-quinolin-6-yl)-2-phenyl-acetamide Structure

7511-77-5

N-(4-amino-2-me...

methyl 3-(2-ethoxyphenyl)propionate Structure

1329812-54-5

methyl 3-(2-eth...

~65%

3-(2-ETHOXYPHENYL)PROPIONIC ACID Structure

220285-28-9

3-(2-ETHOXYPHEN...

2-methyl-6-nitro-1H-quinolin-4-one Structure

112219-43-9

2-methyl-6-nitr...

~71%

4-chloro-2-methyl-6-nitroquinoline Structure

1207-81-4

4-chloro-2-meth...

4-Nitroaniline Structure

100-01-6

4-Nitroaniline

~%

4-chloro-2-methyl-6-nitroquinoline Structure

1207-81-4

4-chloro-2-meth...

4-azido-2-methyl-6-nitroquinoline Structure

1528735-22-9

4-azido-2-methy...

~96%

2-Methyl-4-aMino-6-nitroquinoline Structure

99185-71-4

2-Methyl-4-aMin...

4-Nitroaniline Structure

100-01-6

4-Nitroaniline

~%

2-Methyl-4-aMino-6-nitroquinoline Structure

99185-71-4

2-Methyl-4-aMin...

2-methyl-6-nitro-1H-quinolin-4-one Structure

112219-43-9

2-methyl-6-nitr...

~%

2-Methyl-4-aMino-6-nitroquinoline Structure

99185-71-4

2-Methyl-4-aMin...

4-chloro-2-methyl-6-nitroquinoline Structure

1207-81-4

4-chloro-2-meth...

~%

2-Methyl-4-aMino-6-nitroquinoline Structure

99185-71-4

2-Methyl-4-aMin...

N/A Structure

1261878-63-0

N/A

~93%

3-(5-Bromo-2-methoxyphenyl)propanoic acid Structure

82547-30-6

3-(5-Bromo-2-me...

3-Bromobenzaldehyde Structure

3132-99-8

3-Bromobenzaldehyde

~%

3-(5-Bromo-2-methoxyphenyl)propanoic acid Structure

82547-30-6

3-(5-Bromo-2-me...

(E)-methyl 3-(5-bromo-2-methoxyphenyl)acrylate Structure

1528736-46-0

(E)-methyl 3-(5...

~%

3-(5-Bromo-2-methoxyphenyl)propanoic acid Structure

82547-30-6

3-(5-Bromo-2-me...


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