Efficient synthesis and structure–activity relationship of honokiol, a neurotrophic biphenyl-type neolignan

…, H Zhai, Y Shimizu, Y Mitsumoto, Y Fukuyama

Index: Esumi, Tomoyuki; Makado, Gouki; Zhai, Haifeng; Shimizu, Yasuhiro; Mitsumoto, Yasuhide; Fukuyama, Yoshiyasu Bioorganic and Medicinal Chemistry Letters, 2004 , vol. 14, # 10 p. 2621 - 2625

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Citation Number: 43

Abstract

Honokiol, a biphenyl-type neolignan, which shows the remarkable neurotrophic effect in primary cultured rat cortical neurons, has been effectively synthesized in 21% yield over 14 steps starting from 5-bromosalicylic acid and p-hydroxybenzoic acid by utilizing Pd- catalyzed Suzuki–Miyaura coupling reaction as a key step. Additionally, the structure– activity relationship between neurite outgrowth-promoting activity and its O-methylated ...

 Related Synthetic Route
Honokiol Structure

35354-74-6

Honokiol

(Trimethylsilyl)diazomethane Structure

18107-18-1

(Trimethylsilyl...

~12%

4-(2-methoxy-5-prop-2-enylphenyl)-2-prop-2-enylphenol Structure

68592-19-8

4-(2-methoxy-5-...

4-O-Methyl honokiol Structure

68592-15-4

4-O-Methyl honokiol

Detail
Honokiol Structure

35354-74-6

Honokiol

(Trimethylsilyl)diazomethane Structure

18107-18-1

(Trimethylsilyl...

~12%

4-(2-methoxy-5-prop-2-enylphenyl)-2-prop-2-enylphenol Structure

68592-19-8

4-(2-methoxy-5-...

4-O-Methyl honokiol Structure

68592-15-4

4-O-Methyl honokiol

Detail
5-Bromo-2-hydroxybenzoic acid Structure

89-55-4

5-Bromo-2-hydro...

~%

2-(4-hydroxy-3-propylphenyl)-4-propylphenol Structure

35406-31-6

2-(4-hydroxy-3-...

Methyl 3-bromo-4-hydroxybenzoate Structure

29415-97-2

Methyl 3-bromo-...

~%

2-(4-hydroxy-3-propylphenyl)-4-propylphenol Structure

35406-31-6

2-(4-hydroxy-3-...

Methyl 5-Bromosalicylate Structure

4068-76-2

Methyl 5-Bromos...

~%

2-(4-hydroxy-3-propylphenyl)-4-propylphenol Structure

35406-31-6

2-(4-hydroxy-3-...

Methyl 4-hydroxybenzoate Structure

99-76-3

Methyl 4-hydrox...

~%

2-(4-hydroxy-3-propylphenyl)-4-propylphenol Structure

35406-31-6

2-(4-hydroxy-3-...

(3-bromo-4-methoxymethoxy-phenyl)-methanol Structure

162269-91-2

(3-bromo-4-meth...

~%

2-(4-hydroxy-3-propylphenyl)-4-propylphenol Structure

35406-31-6

2-(4-hydroxy-3-...

methyl 5-bromo-2-(methoxymethoxy)benzoate Structure

711012-12-3

methyl 5-bromo-...

~%

2-(4-hydroxy-3-propylphenyl)-4-propylphenol Structure

35406-31-6

2-(4-hydroxy-3-...

3-bromo-4-methoxymethoxybenzoic acid methyl ester Structure

672922-57-5

3-bromo-4-metho...

~%

2-(4-hydroxy-3-propylphenyl)-4-propylphenol Structure

35406-31-6

2-(4-hydroxy-3-...

((3-bromo-4-(methoxymethoxy)benzyl)oxy)(tert-butyl)dimethylsilane Structure

711012-11-2

((3-bromo-4-(me...

~%

2-(4-hydroxy-3-propylphenyl)-4-propylphenol Structure

35406-31-6

2-(4-hydroxy-3-...

4-Hydroxybenzoic acid Structure

99-96-7

4-Hydroxybenzoi...

~%

2-(4-hydroxy-3-propylphenyl)-4-propylphenol Structure

35406-31-6

2-(4-hydroxy-3-...

methyl 2-(methoxymethoxy)-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzoate Structure

711012-10-1

methyl 2-(metho...

~%

2-(4-hydroxy-3-propylphenyl)-4-propylphenol Structure

35406-31-6

2-(4-hydroxy-3-...

3',5-bis(bromomethyl)-2,4'-bis(methoxymethoxy)-1,1'-biphenyl Structure

711012-16-7

3',5-bis(bromom...

~%

2-(4-hydroxy-3-propylphenyl)-4-propylphenol Structure

35406-31-6

2-(4-hydroxy-3-...

(4,6'-bis(methoxymethoxy)-[1,1'-biphenyl]-3,3'-diyl)dimethanol Structure

711012-13-4

(4,6'-bis(metho...

~%

2-(4-hydroxy-3-propylphenyl)-4-propylphenol Structure

35406-31-6

2-(4-hydroxy-3-...

3',5-diallyl-2,4'-bis(methoxymethoxy)-1,1'-biphenyl Structure

711012-14-5

3',5-diallyl-2,...

~%

2-(4-hydroxy-3-propylphenyl)-4-propylphenol Structure

35406-31-6

2-(4-hydroxy-3-...

methyl 5'-(((tert-butyldimethylsilyl)oxy)methyl)-2',4-bis(methoxymethoxy)-[1,1'-biphenyl]-3-carboxylate Structure

711012-09-8

methyl 5'-(((te...

~%

2-(4-hydroxy-3-propylphenyl)-4-propylphenol Structure

35406-31-6

2-(4-hydroxy-3-...

(5'-(((tert-butyldimethylsilyl)oxy)methyl)-2',4-bis(methoxymethoxy)-[1,1'-biphenyl]-3-yl)methanol Structure

711012-15-6

(5'-(((tert-but...

~%

2-(4-hydroxy-3-propylphenyl)-4-propylphenol Structure

35406-31-6

2-(4-hydroxy-3-...

Honokiol Structure

35354-74-6

Honokiol

(Trimethylsilyl)diazomethane Structure

18107-18-1

(Trimethylsilyl...

~47%

4-(2-methoxy-5-prop-2-enylphenyl)-2-prop-2-enylphenol Structure

68592-19-8

4-(2-methoxy-5-...

4-O-Methyl honokiol Structure

68592-15-4

4-O-Methyl honokiol

Detail
4-Hydroxybenzoic acid Structure

99-96-7

4-Hydroxybenzoi...

~%

Methyl 3-bromo-4-hydroxybenzoate Structure

29415-97-2

Methyl 3-bromo-...


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