Medical Development

SAMEER URGAONKAR

** ******** ****, *** ***, Arlington, MA 02474, Ph: 515-***-****

******.*********@*****.***

VISA STATUS: Permanent Resident

HIGHLIGHTS

Over three years of experience IN AN INTEGRATED PUBLIC-PRIVATE ENTERPRISE

FOCUSED ON ANTIMALARIAL drug discovery, two years of postdoctoral

experience, AND A Ph.D. in Organic Chemistry. Expertise in a wide range of

synthetic organic techniques, INCLUDING METAL-CATALYZED CROSS-COUPLINGS,

homogenous catalysis, amination chemistry.

RESEARCH EXPERIENCE

Research Chemist I, Broad Institute, Infectious Disease Initiative Program,

2007-Present

. Designed and developed a novel two step (compared to 4-5 steps in the

literature) synthetic methodology to access 2-aminoindoles, a novel class

of antimalarials with potent in vitro and in vivo antimalarial activity

expediting the SAR exploration.

. Planned and executed several synthetic routes to access 2-aminoindoles in

gram quantities for DMPK and toxicology studies.

. Developed a short and concise methodology to afford a novel family of

antimalarials based on a benzothiazepine scaffold, prepared ~40 analogs

to establish the SAR and to address the aqueous solubility issues.

. Designed and Conducted SAR studies and lead optimization for antimalarial

drug candidates hydroxythiazoles and benzothiazepine imines.

. Synthesized a solution phase library of more than 2000 plasmodium

falciparum selective HDAC inhibitors.

. Worked closely with Biologists to develop novel antimalarial lead

compounds, in selecting analogs for resistance selection studies and

transfection strategies to explore the mechanism of action of the various

compound classes.

. Interacted with Cheminformatics Scientists to define the chemical space

occupied by global collection of antimalarial compounds.

. Extensively collaborated with Scientists at Genzyme Corporation in the

development of antimalarial drugs.

Postdoctoral Fellow, Harvard Medical School, Harvard University, 2005-2007

Advisor: Prof. Jared T. Shaw

Completed the synthesis of two natural products, dichamanetin and 2"'-

hydroxy-5"-benzylisouvarinol B that targets FtsZ, an essential bacterial

cell division protein, by developing a synthetic methodology in less than

four months.

Designed and executed the synthesis of a diglycosylated flavone,

Kaempferitrin, for which significant antibacterial activity had been

reported.

. Synthesized several alkyne-tagged photo-affinity probes to identify the

target of a small molecule 534F6, discovered in a high-throughput screen,

with bactericidal properties that induces extensive cell filamentation by

an FtsZ-independent mechanism.

. Designed and developed the synthesis of Viriditoxin, a natural product

that targets FtsZ.

EDUCATION

Ph.D. Candidate (Organic Chemistry), Iowa State University, 1999-2004

Advisor: Prof. John G. Verkade

. Developed commercially available proazaphosphatranes (Verkade's

superbases) as ligands for palladium-catalyzed Buchwald-Hartwig

amination, Stille, and Suzuki coupling reactions.

. Designed and synthesized a new triaminophosphine ligand for Buchwald-

Hartwig amination reaction.

. Developed a ligand-, copper-, and amine-free Sonogashira reaction.

. Developed a synthetic methodology for the transition-metal free synthesis

of diaryl ethers promoted by proazaphosphatranes.

B. S. (Hons.), (Chemistry), Indian Institute of Technology (IIT),

Kharagpur, India, 1995-1998

SKILLS

. Strong synthetic organic chemistry knowledge, with a particular emphasis

in designing and executing multi-step syntheses.

. Experience in medicinal chemistry - Hit-to-Lead development, design and

optimization of synthetic routes to afford compound libraries for rapid

SAR exploration.

. Skilled in purification methods (flash chromatography, preparative HPLC)

and analytical techniques (NMR, IR, LC/MS, GC/MS, chiral HPLC, SFC, X-

ray).

. Experience with Databases, eg. Scifinder and Beilstein and Microsoft

Excel, Word, Powerpoint, ChemDraw, E-notebook, Spotfire, Chemaxon.

. Strong interpersonal, communication, and written skills.

AWARDS, HONORS & ACTIVITIES

. Broad Institute's Exceptional Year Award (2008).

. Frank J. Moore and Thoreen Beth Moore Fellowship (2004).

. Invited as a reviewer for the: Journal of the American Chemical Society,

Journal of Organic Chemistry, Organic Letters, Tetrahedron Letters,

Tetrahedron, and Canadian Journal of Chemistry.

SELECTED PUBLICATIONS

1. Dong, C.; Urgaonkar, S.; Cortese, J.; Gamo, F-J.; Lafuente-Monasterio,

M.; Patel, V.; Ross, L.; Dvorin, J.; Duraisingh, M. T.; Wirth D. F.;

Clardy, J.; Mazitschek, R. Identification and validation of tetracyclic

benzothiazepines as Plasmodium falciparum cytochrome bc1 inhibitors. PNAS

2010 submitted. [shared first author]

2. Urgaonkar, S.; Cortese, J. F.; Barker, R. H.; Cromwell, M.; Serrano, A.

E.; Wirth D. F.; Clardy, J.; Mazitschek, R. A Concise Silylamine

Approach to 2-Amino-3-hydroxy-indoles with Potent in vivo Antimalaria

Activity. Org. Lett. 2010, 12, 3998.

3. Patel, V.; Mazitschek, R.; Coleman, B.; Nguyen, C.; Urgaonkar, S.;

Cortese, J.; Barker, R. H.; Greenberg, E.; Tang, W.; Bradner, J. E.;

Schreiber, S. L.; Duraisingh, M. T.; Wirth D. F.; Clardy, J.

Identification and characterization of small molecule inhibitors of a

class I histone deacetylase from Plasmodium falciparum. J. Med. Chem.

2009, 52, 2185.

4. Mukherjee, S.; Robinson, C. A.; Howe, A. G.; Mazor, T.; Wood, P. A.;

Urgaonkar S.; Hebert, A. M; Raychaudhuri, D.; Shaw, J. T. N-Benzyl-3-

sulfonamidopyrrolidines as novel inhibitors of cell division in E. coli.

Bioorg. Med. Chem. Lett. 2007, 17, 6651.

5. Urgaonkar, S.; Shaw, J. T. Synthesis of kaempferitrin. J. Org. Chem.

2007, 72, 4582.

6. Urgaonkar, S.; La Pierre, H. S.; Meir, I.; Lund, H.; RayChaudhuri, D.;

Shaw, J. T. Synthesis of Antimicrobial Natural Products Targeting FtsZ: -Dichamanetin and -2 Hydroxy-5"-benzylisouvarinol-B. Org. Lett.

2005, 7, 5609.

7. Urgaonkar, S.; Verkade, J. G. P(i-BuNCH2CH2)3N: An Efficient Promoter

for the Nucleophilic Aromatic Substitution Reaction of Aryl Fluorides

with Aryl TBDMS (or TMS) Ethers. Org. Lett. 2005, 7, 3319.

8. Su, W.; Urgaonkar, S.; Verkade, J. G. Highly Active Palladium Catalysts

Supported by Bulky Proazaphosphatrane Ligands for Stille Cross-Coupling:

Coupling of Aryl and Vinyl Chlorides, Room Temperature Coupling of Aryl

Bromides, Coupling of Aryl Triflates, and Synthesis of Sterically

Hindered Biaryls. J. Am. Chem. Soc. 2004, 126, 16433.

9. Urgaonkar, S.; Verkade, J. G. Scope and Limitations of Pd2(dba)3/P(i-

BuNCH2CH2)3N-Catalyzed Buchwald-Hartwig Amination Reactions of Aryl

Chlorides. J. Org. Chem. 2004, 69, 9135.

10. Urgaonkar, S.; Verkade, J. G. Ligand-, Copper-, and Amine-Free

Sonogashira Reaction of Aryl Iodides and Bromides with Terminal Alkynes.

J. Org. Chem. 2004, 69, 5752.

11. Urgaonkar, S.; Verkade, J. G. Palladium/Proazaphosphatrane-Catalyzed

Amination of Aryl Halides Possessing a Phenol, Alcohol, Acetanilide,

Amide or an Enolizable Ketone Functional Group: Efficacy of Lithium

Bis(trimethylsilyl)amide as the Base. Adv. Synth. Catal. 2004, 346, 611.

12. Urgaonkar, S.; Nagarajan, M.; Verkade, J. G. P[N(i-Bu)CH2CH2]3N: A

Versatile Ligand for the Pd-Catalyzed Amination of Aryl Chlorides. Org.

Lett. 2003, 5, 815.

13. Urgaonkar, S.; Xu, J.-H.; Verkade, J. G. Application of a New Bicyclic

Triaminophosphine Ligand in Pd-Catalyzed Buchwald-Hartwig Amination

Reactions of Aryl Chlorides, Bromides, and Iodides. J. Org. Chem. 2003,

68, 8416.

14. Urgaonkar, S.; Nagarajan, M.; Verkade, J. G. P(i-BuNCH2CH2)3N: An

Effective Ligand in the Palladium-Catalyzed Amination of Aryl Bromides

and Iodides. J. Org. Chem. 2003, 68, 452.

PATENTS

1. Synthesis of flavanone inhibitors of FtsZ as antibiotics. Shaw, J.;

Urgaonkar, S.; RayChaudhuri, D.; La Pierre, H., PCT Int. Appl. (2007),

WO 200-***-****.

2. Triaminophosphine Ligands for Carbon-Nitrogen and Carbon-Carbon Bond

Formation. Verkade, J. G., Urgaonkar, S.; Xu, J.-H., US Patent (2008),

US 7385058.

3. Palladium-catalyzed coupling of aryl halides with alkynes. Urgaonkar,

S.; Verkade, J. G., US Patent (2010), US 7642391.

SELCTED PRESENTATIONS

1. Urgaonkar, S.; Mazitschek, R.; Celatka, C.; Cortese, J. F.; Liu, H.;

Cromwell, M.; Barker Jr., R. H.; Garcia Rosa, M. I.; Serrano, A. E.;

Wirth, D. F.; Clardy, J.; Wiegand, R.; Sybertz, E. A Novel Chemotype with

Potent Activity Against Plasmodium Falciparum and P. Berghei. Poster

Presentation at The American Society of Tropical Medicine and Hygiene

57th Annual Meeting, New Orleans, LA, December 7-11, 2008.

2. Verkade, J. G., Urgaonkar, S.; Nagarajan, M. P[N(i-Bu)CH2CH2]3N: A

Versatile Ligand for the Pd-Catalyzed Amination of Aryl Chlorides. Paper

# 52, Oral Presentation at 225th ACS National Meeting, New Orleans, LA,

March 23-27, 2003.

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