Synthesis of a novel series of tricyclic indan derivatives as melatonin receptor agonists

…, S Hinuma, K Kato, H Nishikawa, K Hirai…

Index: Uchikawa, Osamu; Fukatsu, Kohji; Tokunoh, Ryosuke; Kawada, Mitsuru; Matsumoto, Kiyoharu; Imai, Yumi; Hinuma, Shuji; Kato, Koki; Nishikawa, Hisao; Hirai, Keisuke; Miyamoto, Masaomi; Ohkawa, Shigenori Journal of Medicinal Chemistry, 2002 , vol. 45, # 19 p. 4222 - 4239

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Citation Number: 123

Abstract

To develop a new therapeutic agent for sleep disorders, we synthesized a novel series of tricyclic indan derivatives and evaluated them for their binding affinity to melatonin receptors. In our previous paper, we proposed a conformation of the methoxy group favorable for the binding of the MT1 receptor. To fix the methoxy group in an active conformation, we decided to synthesize conformationally restricted tricyclic indan analogues with the oxygen atom in ...

 Related Synthetic Route
Coumaran Structure

496-16-2

Coumaran

~%

5,6-dihydro-2H-indeno[5,6-b]furan-7(3H)-one Structure

448964-30-5

5,6-dihydro-2H-...

2,3-Dihydro-1-benzofuran-5-carbaldehyde Structure

55745-70-5

2,3-Dihydro-1-b...

~%

5,6-dihydro-2H-indeno[5,6-b]furan-7(3H)-one Structure

448964-30-5

5,6-dihydro-2H-...

(2E)-2-[(2E)-2-(1,3,3-TRIMETHYL-1,3-DIHYDRO-2H-INDOL-2-YLIDENE)ETHYLIDENE]-3,4-DIHYDRONAPHTHALEN-1(2H)-ONE Structure

203505-84-4

(2E)-2-[(2E)-2-...

~%

5,6-dihydro-2H-indeno[5,6-b]furan-7(3H)-one Structure

448964-30-5

5,6-dihydro-2H-...

3-(2,3-Dihydro-1-benzofuran-5-yl)propanoic acid Structure

215057-28-6

3-(2,3-Dihydro-...

~%

5,6-dihydro-2H-indeno[5,6-b]furan-7(3H)-one Structure

448964-30-5

5,6-dihydro-2H-...

6-Methoxy-1-indanone Structure

13623-25-1

6-Methoxy-1-indanone

~%

(S)-N-[2-[7-Allyl-5-bromo-2,3-dihydro-6-hydroxy-1H-inden-1-yl]ethyl]propanamide Structure

196597-86-1

(S)-N-[2-[7-All...

(2E)-2-(2,3-Dihydro-6-methoxy-1H-inden-1-ylidene)acetonitrile Structure

187871-98-3

(2E)-2-(2,3-Dih...

~%

(S)-N-[2-[7-Allyl-5-bromo-2,3-dihydro-6-hydroxy-1H-inden-1-yl]ethyl]propanamide Structure

196597-86-1

(S)-N-[2-[7-All...

(2E)-2-(2,3-Dihydro-6-methoxy-1H-inden-1-ylidene)ethanamine Structure

178676-73-8

(2E)-2-(2,3-Dih...

~%

(S)-N-[2-[7-Allyl-5-bromo-2,3-dihydro-6-hydroxy-1H-inden-1-yl]ethyl]propanamide Structure

196597-86-1

(S)-N-[2-[7-All...

(E)-N-[2-(2,3-Dihydro-6-methoxy-1H-inden-1-ylidene)ethyl]propanamide Structure

196597-82-7

(E)-N-[2-(2,3-D...

~%

(S)-N-[2-[7-Allyl-5-bromo-2,3-dihydro-6-hydroxy-1H-inden-1-yl]ethyl]propanamide Structure

196597-86-1

(S)-N-[2-[7-All...

(S)-N-[2-(5-Bromo-2,3-dihydro-6-hydroxy-1H-inden-1-yl)ethyl]propanamide Structure

196597-84-9

(S)-N-[2-(5-Bro...

~%

(S)-N-[2-[7-Allyl-5-bromo-2,3-dihydro-6-hydroxy-1H-inden-1-yl]ethyl]propanamide Structure

196597-86-1

(S)-N-[2-[7-All...

(S)-N-[2-(5-Bromo-2,3-dihydro-6-methoxy-1H-inden-1-yl)ethyl]propanamide Structure

196597-83-8

(S)-N-[2-(5-Bro...

~%

(S)-N-[2-[7-Allyl-5-bromo-2,3-dihydro-6-hydroxy-1H-inden-1-yl]ethyl]propanamide Structure

196597-86-1

(S)-N-[2-[7-All...

6-Methoxy-1-indanone Structure

13623-25-1

6-Methoxy-1-indanone

~%

rac-N-[2-(2,3-Dihydro-6-methoxy-1H-inden-1-yl)ethyl]propanamide Structure

178677-89-9

rac-N-[2-(2,3-D...

(2E)-2-(2,3-Dihydro-6-methoxy-1H-inden-1-ylidene)acetonitrile Structure

187871-98-3

(2E)-2-(2,3-Dih...

~%

rac-N-[2-(2,3-Dihydro-6-methoxy-1H-inden-1-yl)ethyl]propanamide Structure

178677-89-9

rac-N-[2-(2,3-D...

Methanesulfonyl chloride Structure

124-63-0

Methanesulfonyl...

(S)-N-[2-[2,3-Dihydro-6-hydroxy-7-(2-hydroxyethyl)-1H-inden-1-yl]ethyl]propanamide Structure

196597-88-3

(S)-N-[2-[2,3-D...

~86%

Ramelteon Structure

196597-26-9

Ramelteon

(E)-(1,6,7,8-Tetrahydro-2H-indeno[5,4-b]furan-8-ylidene)acetonitrile Structure

196597-79-2

(E)-(1,6,7,8-Te...

~79%

2-(2,6,7,8-tetrahydro-1H-cyclopenta[e][1]benzofuran-8-yl)ethanamine Structure

448964-37-2

2-(2,6,7,8-tetr...

Coumaran Structure

496-16-2

Coumaran

~%

2-(2,6,7,8-tetrahydro-1H-cyclopenta[e][1]benzofuran-8-yl)ethanamine Structure

448964-37-2

2-(2,6,7,8-tetr...

2,3-Dihydro-1-benzofuran-5-carbaldehyde Structure

55745-70-5

2,3-Dihydro-1-b...

~%

2-(2,6,7,8-tetrahydro-1H-cyclopenta[e][1]benzofuran-8-yl)ethanamine Structure

448964-37-2

2-(2,6,7,8-tetr...

Ethyl 3-(2,3-Dihydrobenzofuran-5-yl)propenoate Structure

196597-65-6

Ethyl 3-(2,3-Di...

~%

2-(2,6,7,8-tetrahydro-1H-cyclopenta[e][1]benzofuran-8-yl)ethanamine Structure

448964-37-2

2-(2,6,7,8-tetr...

1,2,6,7-Tetrahydro-8H-indeno[5,4-b]furan-8-one Structure

196597-78-1

1,2,6,7-Tetrahy...

~%

2-(2,6,7,8-tetrahydro-1H-cyclopenta[e][1]benzofuran-8-yl)ethanamine Structure

448964-37-2

2-(2,6,7,8-tetr...

Ethyl 3-(2,3-Dihydrobenzofuran-5-yl)propanoate Structure

196597-66-7

Ethyl 3-(2,3-Di...

~%

2-(2,6,7,8-tetrahydro-1H-cyclopenta[e][1]benzofuran-8-yl)ethanamine Structure

448964-37-2

2-(2,6,7,8-tetr...

Ethyl 3-(7-Bromo-2,3-dihydro-1-benzofuran-5-yl)propanoate Structure

196597-67-8

Ethyl 3-(7-Brom...

~%

2-(2,6,7,8-tetrahydro-1H-cyclopenta[e][1]benzofuran-8-yl)ethanamine Structure

448964-37-2

2-(2,6,7,8-tetr...

N/A Structure

227179-21-7

N/A

~%

2-(2,6,7,8-tetrahydro-1H-cyclopenta[e][1]benzofuran-8-yl)ethanamine Structure

448964-37-2

2-(2,6,7,8-tetr...

4,5-Dibromo-1,2,6,7-tertahydro-8H-indeno[5,4-b]furan-8-one Structure

196597-77-0

4,5-Dibromo-1,2...

~%

2-(2,6,7,8-tetrahydro-1H-cyclopenta[e][1]benzofuran-8-yl)ethanamine Structure

448964-37-2

2-(2,6,7,8-tetr...

3-(6,7-Dibromo-2,3-dihydrobenzofuran-5-yl)propanoic Acid Structure

196597-76-9

3-(6,7-Dibromo-...

~%

2-(2,6,7,8-tetrahydro-1H-cyclopenta[e][1]benzofuran-8-yl)ethanamine Structure

448964-37-2

2-(2,6,7,8-tetr...

Ethyl 3-(6,7-Dibromo-2,3-Dihydrobenzofuran-5-Yl)Propanoate Structure

196597-75-8

Ethyl 3-(6,7-Di...

~%

2-(2,6,7,8-tetrahydro-1H-cyclopenta[e][1]benzofuran-8-yl)ethanamine Structure

448964-37-2

2-(2,6,7,8-tetr...


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