PSK-Expansion of Indolizine Chemical Space-Dirgha.pptx

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Dr. Dirgha Raj Joshi

A presentation about synthesis of indolizines presented a Pharmaceutical society of Korea conference.

Health & Medicine

Dirgha Raj Joshi
PhD Candidate
Medicinal Chemistry lab,
College of Pharmacy, Yonsei University
Email: djmeropaila121@yonsei.ac.kr
Supervisor: Prof. Ikyon Kim
Expansion of Indolizine Chemical Space:
Synthesis of Poly-Functionalized Indolizines

Some Biologically Active Quinone-Indolizines
J. Org. Chem. 2020, 85, 10994–11005.

Access to Quinone−Indolizine Hybrids
Synthesis 2010, 23, 4007−4014.
J. Org. Chem. 2014, 79, 3992-3998
Formation of pyrrole ring (previous works)
• quinone-indolizine adducts via [4+2] annulative approach
Formation of pyridine ring (this work)

entry base (equiv) Solvent time (h) Temp. (°C) yield (%)b
1 TEA (1) EtOH 12 rt 82
2 DEA (1) EtOH 12 rt 78
3 DBU (1) EtOH 12 rt 73
4 DIPEA (1) EtOH 12 rt 60
5 DABCO (1) EtOH 12 rt 50
6 - EtOH 12 60 -
7 NaHCO3 (2) EtOH 7 50 -
8 Na2CO3 (1) EtOH 12 50 70
9 TEA (1) DMSO 3 rt 79
10 TEA (1) DMF 4 rt 76
11 TEA (2) CH3CN 4 rt 68
Reaction optimization

Anticancer activity against PC-3 and CAL-27 cells
compound PC-3 CAL-27
4p 0.024 ± 0.008 0.028 ± 0.007
mitoxantrone 1.10 ± 0.14 1.32 ± 0.18
doxorubicin 0.18 ± 0.04 0.21 ± 0.06
J. Org. Chem. 2020, 85, 10994–11005.
• almost all the compounds potently reduced cell viability (IC50 < 2 μM)
• 4p showed ∼48 times stronger inhibitory effect on cell viability than mitoxantrone

Further Expansion of Indolizine Chemical Spaces
• Michael-Aldol-Double Elimination Cascade to Make Pyridines
• Use of Chromone for the Synthesis of Indolizines

Acknowledgement
• Prof. Ikyon Kim: Current Supervisor
• Prof. Hak Sung Kim: MS Pharmacy Supervisor
• Yonsei University for providing Global Leader Scholarship
• Lab members:
Dr. Anuradha Dagar
Sunhee Lee
Sunmi Kim
Seonghyeon Nam

I’m a Responsible Scientist skilled in small molecule chiral and achiral molecule development enthusiastically looking for an opportunity to use my background for API (Active Pharmaceutical Ingredient) development by leveraging demonstrated strategies synthetic route development, cost-reduction and project management while interacting with cross-functional teams to contribute high-quality outcome for Pharmaceuticals. I am highly looking forward to discuss further opportunities with you. Please don't hesitate to contact me > ramesh.yella@aol.com

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PSK-Expansion of Indolizine Chemical Space-Dirgha.pptx

1. Dirgha Raj Joshi PhD Candidate Medicinal Chemistry lab, College of Pharmacy, Yonsei University Email: djmeropaila121@yonsei.ac.kr Supervisor: Prof. Ikyon Kim Expansion of Indolizine Chemical Space: Synthesis of Poly-Functionalized Indolizines

2. Some Biologically Active Quinone-Indolizines J. Org. Chem. 2020, 85, 10994–11005.

3. Access to Quinone−Indolizine Hybrids Synthesis 2010, 23, 4007−4014. J. Org. Chem. 2014, 79, 3992-3998 Formation of pyrrole ring (previous works) • quinone-indolizine adducts via [4+2] annulative approach Formation of pyridine ring (this work)

4. entry base (equiv) Solvent time (h) Temp. (°C) yield (%)b 1 TEA (1) EtOH 12 rt 82 2 DEA (1) EtOH 12 rt 78 3 DBU (1) EtOH 12 rt 73 4 DIPEA (1) EtOH 12 rt 60 5 DABCO (1) EtOH 12 rt 50 6 - EtOH 12 60 - 7 NaHCO3 (2) EtOH 7 50 - 8 Na2CO3 (1) EtOH 12 50 70 9 TEA (1) DMSO 3 rt 79 10 TEA (1) DMF 4 rt 76 11 TEA (2) CH3CN 4 rt 68 Reaction optimization

5. Crystal Structure of 4s Reaction Scope

6. Further Application

7. Anticancer activity against PC-3 and CAL-27 cells compound PC-3 CAL-27 4p 0.024 ± 0.008 0.028 ± 0.007 mitoxantrone 1.10 ± 0.14 1.32 ± 0.18 doxorubicin 0.18 ± 0.04 0.21 ± 0.06 J. Org. Chem. 2020, 85, 10994–11005. • almost all the compounds potently reduced cell viability (IC50 < 2 μM) • 4p showed ∼48 times stronger inhibitory effect on cell viability than mitoxantrone

8. Further Expansion of Indolizine Chemical Spaces • Michael-Aldol-Double Elimination Cascade to Make Pyridines • Use of Chromone for the Synthesis of Indolizines

9. Conclusion

10. Acknowledgement • Prof. Ikyon Kim: Current Supervisor • Prof. Hak Sung Kim: MS Pharmacy Supervisor • Yonsei University for providing Global Leader Scholarship • Lab members: Dr. Anuradha Dagar Sunhee Lee Sunmi Kim Seonghyeon Nam

PSK-Expansion of Indolizine Chemical Space-Dirgha.pptx

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