Shaik Work Summary
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Work Summary Medicinal chemistry (Synthesis and biological evolution of new molecules based on thiolactomycin against Mycobacterium tuberculosisH37Rv and P. falciparaum) 1. A combinatorial approach for the synthesis of new molecules based on thiolactomycin active against tuberculosis and malaria S
O
O
O O S N R
a b c d n 2 3 4 5
( )n N
e
f
g h
6 8
i
9 10 12
R= Phenyl, Tolyl, 1-napthyl, 2-napthyl, 8-quinolinyl, 4-FC6H5, 2,4-C6H4 etc.,
Commucnicated 2008 (J. Comb. Chem.) 2. Synthesis and biological evaluation of thiolactone based analogues as potential antimalarial agents S
O
O O
( )n
N N
( )n
O
O
( )n
O
O
S O
S
S
O
f
g h
S O
( )n
N N
( )n
a b c d
O
n 2 3 5 6 S
e
8 9 10 12
O
Communicated 2008 (Eur. J. Med. Chem.) 3. Efforts towards the development of new antitubercular agents: Potential for thiolactomycin based compounds J. Pharm. Pharmaceut. Sci. 2008, 11, 56s-80s. Dedicated in memory of Ronald G. Micetisch
Organic chemistry Synthesis of pharmaceutically important compounds 1. Enantioselective synthesis of (3R,4R)- and (3S,4S)-dihydroxy pyrrolidine by catalytic and biocatalytic approach Biocatalytic Approach HO
OH
HO +
N Cbz (3S,4S)
OAc
HO
N Cbz (3R,4R)
OAc N Cbz (±)
Catalytic Approach HO
O
OH
N Cbz (±)
N Cbz (3R,4R)
Tetrahedron: Asymmetry 2008 (Communicated) 2. Lipase mediated resolution of γ-azidoalcohols in aqueous and organic media: Synthesis of (R)-and (S)-fluoxetine and duloxetine CF3 OH
O NHCH3
NHCH3 N3
O
OH S
N3
S Fluoxetine
duloxetine
J. Mol. Cat. B: Enzyme 2008 (Accepted)
3. Synthesis of enantiomerically pure γ-azidoalcohols by lipase-catalyzed transesterification O OH R
OH
lipase PS-D
N3
n-hexane,
O
R
OAc
N3
+
R
(S)
N3 (R)
R= C6H5, 4-BrC6H4,4-ClC6H4, 4-MeC6H4, 4-OMeC6H4, 2-Thienyl
Tetrahedron: Asymmetry 2008, 19, 1078. 4. Enantioselective synthesis of (R)- and (S)-curcumene and curcuphenol: an efficient chemoenzymatic route
HO
(S)-Curcumene
(S)-Curcuphenol Tetrahedron: Asymmetry 2007, 18, 2547.
5. Chemoenzymatic
synthesis
of
(3R,4S)-
and
(3S,4R)-3-methoxy-4-
methylaminopyrrolidine H3CO
NCH3Boc
N Boc (3R,4S) H3CO
NCH3Boc
HO
N3 N Cbz
N H
(±) N Boc (3S,4R)
Tetrahedron: Asymmetry 2006, 17, 2876.
6. Chemoenzymatic synthesis of (5S)- and (5R)-hydroxymethyl-3,5 dimethyl-4(methoxymethoxy)-5H-thiophen-2-one: a precursor of thiolactomycin and determination of its absolute configuration
O
S
OAc C.Papaya O
(±)
OMOM
S
H3CO
OAc
+ (S)
OMOM
O F 3C
S
O
OH
(R)
OMOM
O S
O
O
O O
A model with (R)-MTPA ester
F 3C H3CO
S
O
O
O O
A model with (S)-MTPA ester
Tetrahedron: Asymmetry 2006, 17, 2890.
O
O
O O S N R
a b c d n 2 3 4 5
( )n N
e
f
g h
6 8
i
9 10 12
R= Phenyl, Tolyl, 1-napthyl, 2-napthyl, 8-quinolinyl, 4-FC6H5, 2,4-C6H4 etc.,
Commucnicated 2008 (J. Comb. Chem.) 2. Synthesis and biological evaluation of thiolactone based analogues as potential antimalarial agents S
O
O O
( )n
N N
( )n
O
O
( )n
O
O
S O
S
S
O
f
g h
S O
( )n
N N
( )n
a b c d
O
n 2 3 5 6 S
e
8 9 10 12
O
Communicated 2008 (Eur. J. Med. Chem.) 3. Efforts towards the development of new antitubercular agents: Potential for thiolactomycin based compounds J. Pharm. Pharmaceut. Sci. 2008, 11, 56s-80s. Dedicated in memory of Ronald G. Micetisch
Organic chemistry Synthesis of pharmaceutically important compounds 1. Enantioselective synthesis of (3R,4R)- and (3S,4S)-dihydroxy pyrrolidine by catalytic and biocatalytic approach Biocatalytic Approach HO
OH
HO +
N Cbz (3S,4S)
OAc
HO
N Cbz (3R,4R)
OAc N Cbz (±)
Catalytic Approach HO
O
OH
N Cbz (±)
N Cbz (3R,4R)
Tetrahedron: Asymmetry 2008 (Communicated) 2. Lipase mediated resolution of γ-azidoalcohols in aqueous and organic media: Synthesis of (R)-and (S)-fluoxetine and duloxetine CF3 OH
O NHCH3
NHCH3 N3
O
OH S
N3
S Fluoxetine
duloxetine
J. Mol. Cat. B: Enzyme 2008 (Accepted)
3. Synthesis of enantiomerically pure γ-azidoalcohols by lipase-catalyzed transesterification O OH R
OH
lipase PS-D
N3
n-hexane,
O
R
OAc
N3
+
R
(S)
N3 (R)
R= C6H5, 4-BrC6H4,4-ClC6H4, 4-MeC6H4, 4-OMeC6H4, 2-Thienyl
Tetrahedron: Asymmetry 2008, 19, 1078. 4. Enantioselective synthesis of (R)- and (S)-curcumene and curcuphenol: an efficient chemoenzymatic route
HO
(S)-Curcumene
(S)-Curcuphenol Tetrahedron: Asymmetry 2007, 18, 2547.
5. Chemoenzymatic
synthesis
of
(3R,4S)-
and
(3S,4R)-3-methoxy-4-
methylaminopyrrolidine H3CO
NCH3Boc
N Boc (3R,4S) H3CO
NCH3Boc
HO
N3 N Cbz
N H
(±) N Boc (3S,4R)
Tetrahedron: Asymmetry 2006, 17, 2876.
6. Chemoenzymatic synthesis of (5S)- and (5R)-hydroxymethyl-3,5 dimethyl-4(methoxymethoxy)-5H-thiophen-2-one: a precursor of thiolactomycin and determination of its absolute configuration
O
S
OAc C.Papaya O
(±)
OMOM
S
H3CO
OAc
+ (S)
OMOM
O F 3C
S
O
OH
(R)
OMOM
O S
O
O
O O
A model with (R)-MTPA ester
F 3C H3CO
S
O
O
O O
A model with (S)-MTPA ester
Tetrahedron: Asymmetry 2006, 17, 2890.
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