Organic
Chemistry
Overview
The organic chemistry group is engaged in multifaceted activities ranging from process chemistry, custom synthesis, synthesis of new chemical entities with clinical potentials and small library synthesis for combinatorial chemistry. The focus is on molecules with commercial value. The group has a team of excellent synthetic chemists who can design and execute complex multi step organic synthesis from flask level to kg scale
Mission
& Goals
- Provide process chemistry solutions to the synthesis of complex organic chemicals
- Produce small molecules for clinical trials
- Asymmetric synthesis of complex bio-active molecules, development of chiral separation technology, resolution and chiron approach
- Isolation and screening of secondary metabolites from plants for bioactivity
- Synthesis of chiral building blocks by biotransformations
Competencies
- Retrosynthetic
design and execution of multistep organic synthesis
- Asymmetric synthesis
- Process chemistry and scale up
capabilities upto kg level
- Biocatalytic
transformations
- Isolation, structure determination and
screening of bioactivity in isolates from natural products
- Color chemistry
with focus on colorants for plastics
Facilities
- Analytical and preparative HPLC units
- Gas chromatographs
- GC-Mass spectrometer
- High Performance TLC
- Ion chromatography unit
- IR and UV spectrophotometers
- Digital Polarimeter
- Micro-analysis units
- SEPBOX (fractionation of crude plant extract)
- LC-MS-MS-TOF
Glimpses
of current research
- Development of process chemistry for Zidovudine, Lamivudine, Nevirapine, Efavirenz, Abacavir, Irinotecan,Capecitabine, Imatinib, Atorvastatin, Vanlafaxine, Meropenem, Pioglitaxone, Olanzapine, Femciclovir, Repaglinide
- To synthesize and evaluate small molecules as potential clinical candidates for infectous, cancer, fungal, inflammation/COX-II, obesity, and tuberculosis
- To isolate naturally occurring compounds from plants as potential drug candidates
- Development of chemistry for chiral drugs such as (S)-Amlodipine, levo-Citirizine, R-Salbutamol, (S)-Citalopram
- Development of chemistry for chiral drugs as fine chemicals such as (S)-3-hydroxy-butyrolactone, (R) and (S)- gepichlorohydrin, (R ) and (S)- 4-hydroxy-cyclopent-2-enone, D-phenyl-glycine 4-hydroxy-D-phenylglycine
- Development of plant growth regulators, pesticides, and chemical hybridizing agents, such as Ethephon, maleic hydrazide, paclobutrazole, Glyphosate, F-7967
Basic Research
Asymmetric total synthesis
Chiral molecules produced by living organisms are endowed with fascinating structural elements. The total synthesis of the following bioactive molecules have been completed: camptothecin, sangliferins, biotin, vancomycin, zarazozic acid, fumonicins, stemoamide, lasonolide A, pironetin, panaxytriol, triquinane analogues, manzacidins, slagenins, Aal toxins.
New synthetic methodology
A new rearrangement in nucleoside chemistry has been discovered, which has been extended to make anti-AIDS drugs successfully (US Patent, 5,596,087). Similarly, a protocol to selectively alkylate the fluoronitrobenzene has found application in anti-psychotic drug Ziprasidone (Synthesis, 2000, 1659). Like wise one step catalytic hydrogenation of nitrile providing dimethylamino functionality has found its application in a process for manufacturing an antidepressant drug Vanalafaxine (US Patent 6,350,912).
Combined use of ultrasound and nano-particle catalysts has led to an efficient Heck reaction. (Chem Comm., 2001, 1544). gem-Diallyl functionality was introduced on an inactive carbon by radical ring opening of cyclopropyl methyl halide with allyl-tri-butyltin (Chem Comm., 2001, 241 and 917). This reaction was used to synthesise an aesthetically appealing molecule, namely, tetrakis (cyclopropylmethyl) methane (Chem Comm., 2002, 315).
Carbohydrate chemistry
Apart from the use of carbohydrates as chiral building blocks work is in progress on the synthesis of oligo-saccharide present on the cell wall surface of mycobacterium tuberculosis, particularly the arabino-galactan based motifs (Org Lett, 2001, 321; J Org Chem., 2001, 4657). The synthesis of new and potent anti-viral nucleosides is also a topic of current interest (J Org. Chem., 2001, 7552).
Contact
Dr. MK Gurjar
National Chemical Laboratory ,
Pune 411 008
Email
:gurjar@dalton.ncl.res.in
Phone
:+91-20-25893543, 2588 2456
Fax
:+91-20-2589 3614