Accepted Manuscript Design, Synthesis and Antiproliferative Activity of Functionalized Flavone-TriazoleTetrahydropyran Conjugates Against Human Cancer Cell Lines Naseem Ahmed , Naveen Kumar Konduru , Sarfaraz Ahmad , Mohammad Owais PII:

S0223-5234(14)00528-5

DOI:

10.1016/j.ejmech.2014.06.009

Reference:

EJMECH 7052

To appear in:

European Journal of Medicinal Chemistry

Received Date: 13 April 2014 Revised Date:

27 May 2014

Accepted Date: 5 June 2014

Please cite this article as: N. Ahmed, N.K. Konduru, S. Ahmad, M. Owais, Design, Synthesis and Antiproliferative Activity of Functionalized Flavone-Triazole-Tetrahydropyran Conjugates Against Human Cancer Cell Lines, European Journal of Medicinal Chemistry (2014), doi: 10.1016/j.ejmech.2014.06.009. This is a PDF file of an unedited manuscript that has been accepted for publication. As a service to our customers we are providing this early version of the manuscript. The manuscript will undergo copyediting, typesetting, and review of the resulting proof before it is published in its final form. Please note that during the production process errors may be discovered which could affect the content, and all legal disclaimers that apply to the journal pertain.

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Design, Synthesis and Antiproliferative Activity of Functionalized Flavone-Triazole-

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Tetrahydropyran Conjugates Against Human Cancer Cell Lines

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Table 2: The solvent effects on triazole yield. Solvent

Time

Yield

1

ACN

3

68

2

MeOH

5

3

THF

1

4

THF:H2O

4

5

EtOAc

6

65

6

Toluene

6

60

7

DMF

8

Water

9 10

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Entry

60

95

73

60

nr

nr

ACN:H2O

4

70

acetone

3

72

TE D

6

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Table 3: Synthesis of 5-iodotriazoles from 4-azido tetrahydropyrans and flavone based alkynes.

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Cl O

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O

N N

O

N

I

O

Cl

Cl

3j

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MeO O O N N

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O N

I

O

F

Cl

3k

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MeO

O

RI PT

O N N

O N

O OMe

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4a

MeO

O N N

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O

O N

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O

OMe

4a

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MeO O O N N

O N

O Br

4c

OMe

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Cl O O N N

O

AC C

N

O

Br

4e

Br

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MeO

O O N N

O

AC C

N

O

Br

Br

4g

MeO

O O N N

O N

O Br

Br

4g

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Design, synthesis and antiproliferative activity of functionalized flavone-triazole-tetrahydropyran conjugates against human cancer cell lines.

Under optimized reaction conditions, an efficient synthetic method has been developed to afford the functionalized flavone-triazole-tetrahydropyran co...
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