University of Groningen
MCR-Based Exploitation and Application of Diverse (Poly)Heterocyclic Scaffolds
Wang, Qian
DOI:
10.33612/diss.133937133
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Publication date: 2020
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Wang, Q. (2020). MCR-Based Exploitation and Application of Diverse (Poly)Heterocyclic Scaffolds. University of Groningen. https://doi.org/10.33612/diss.133937133
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A P P E N D I C E S
Acknowledgements
Conferences
List of Publications
ACKNOWLEDGEMENTS
249
Acknowledgements
Here it ends! Completing this thesis, a product of four years’ work, I feel deeply indebted to a great many people who have greatly inspired and supported me during my Ph.D. study at University of Groningen. The work presented in this thesis would not have been possible without my close association with dozens of remarkable individuals. It is not a fair task to acknowledge all the people who made this Ph.D. thesis possible with a few words. However, I will try my best to convey my sincere thanks to everyone who helped me scientifically and emotionally throughout this journey.
First and foremost, I would like to express my sincere gratitude to my mentor & promotor, Prof. Alexander Dömling for providing me an opportunity to be one of the leaves of your academic family tree. For your invaluable guidance, encouragement, academic stimulus and generous help to my Ph.D. study with your time, patience, unlimited enthusiasm and immense knowledge, which supported me in all the time of research and writing of this thesis. You are very generous, kind, humorous and helpful person. From Alex, I learnt, not only the state-of-the-art knowledge of chemistry and biology, but also the rigorous scientific approach and the dedicating spirit for work. I am so thankful for the excellent example you have provided as a successful researcher and professor. I will never forget your openness and willingness for any discussion, you keep your office door open all the time and everyone can come to you to get help easily. I will always remember the way you lead the group to create an excellent work environment and keep a very high output. I deeply appreciate the fact that you always made room for my interests that I can put forward some ideas of my own and try them. I’ll be forever grateful for the opportunity I had to work closely with you for four years.
I would like to thank my co-promotor, Prof. Matthew Groves, thank you for the great help with the yearly PhD evaluation, my thesis submission, and job hunting. You are a very friendly, kind and easygoing person that I feel very easy to talk with you. Thank you, Prof. Groves.
I would like to acknowledge the members of the reading committee: Prof. Adriaan Minnaard, Prof. Frank Dekker, and Prof. Thomas Müller for their time and efforts to evaluate and approve this thesis, for the valuable comments and suggestions.
Dear Jolanda, I am very grareful to you for the help with various administrative issues, conferences and sending packages. Thank you so much.
My sincere gratitude to our lab manager, Dr. André Boltjes for your huge help to me in many aspects. You greeted me with a smile-full every day and helped me solve chemistry problems and gave me valuable advice in the group meeting. You are an elegant and tasteful man, I learnt a lot from you about fashion, watch and auto knowledge in addition to chemistry. I was happy to witness that you earned the PhD title and started a new career. All the best, André! Robin, our second lab manager, thank you for your invaluable contribution in maintaining the lab in a non-chaotic state. You were very helpful to assist in equipment usage and problems and schedule the group meetings. Thank you for all the help, Robin. Also many thanks to Rick for the great help in the lab. Thanks a lot.
I will never forget the help from my daily supervisor Dr. Rudrakshula Madhavachary. Chary, you taught me how to conduct MCR chemistry and to operate the instruments in our group. Working with you is a very enjoyable and happy thing. Without your help, I couldn’t have finished my study smoothly. Miss you and best wishes for you.
ACKNOWLEDGEMENTS
250
I would like to thank Dr. Constantinos Neochoritis who always there to help, from the supervision and collaboration of my research projects to the examing aspect of thesis and defense process without vacillating at all. Dinos, thanks for sharing your ideas and expertise about research and successful experience for projects. I feel very lucky to have you as a close friend that can communicate and get help at any time. Now you are running your own research group and I wish you a big success in your academic future.
Markella, my best friend, I cannot find words to express my gratitude to you. Your supports is critical to my Ph.D. career. You are trustable that I can share any good or bad moments without any hesitation. We have done a lot of work together brilliantly, and these have become beautiful memories. Thank you, Markella, wish you all the best in San Francisco! Tryfonas, a fabulous friend, you are always there to help everyone. Thank you, Tryf.
My Ph.D. paranymph, Lin, thank you for the willingness to help me with the defense. You are nothing but a just ideal friend and compassionate and pretty. Your suggestions and comments during paper writing and job hunting are valuable for me. I really enjoyed all the conversations with you which are informative and relaxing. Lin, wish you a happy ending here and a glorious future!
Roberto, my Ph.D. paranymph, co-author & brother, I want to express my warmest feelings to you. Your helping and kind nature is beneficial to everyone around you. You ideally combine the warmth and friendliness of the Italian and the diligence and rigor of the German, make every friend feel good and every work go smoothly. Thank you, berto, for everything!
Hao and Bin, I cannot imagine how my Ph.D. career would go forward without you. Hao, you took care of me like an elder brother and took me to visit many beautiful places. You are very helpful and efficient, with excellent communication and leadership skills. I am your most frequent visitor and I will always remember the fantastic time with you. Bin, every time I encounter difficulties, I will ask you for help. You will always help me analyze patiently and find the best solution. You have a great sense of humour and the conversation with you is always full of laughter. Bin and Hao, you are the best, I can foresee your great success in the near future!
I owe a huge debt of gratitude to my beautiful friends Jingyao, Shuxian, Xiaoxiang, and Yu. Jingyao, we joined the group in the same day, and we did have a wonderful time in and out of the lab for 4 years. You are sincere, warm and kind, everyone in the group treats you as the best friend. How lucky I am that have you around me, almost every day. Shuxian, there are far more words between us than with other friends. You have a very good sense of fashion and the excellent cooking skill, I am always ready to accept your invitation for a meal. Xiaoxiang, like the moon in the night sky, you were very hardworking and did your job very well. I really enjoyed the debate with you about “biomaterial and medicinal chemistry, which is a better research area.” Yu, you are very smart to be able to make everyone feel very comfortable and the special care from you often touched me. In addition, you can understand my jokes and respond to me funnily. Girls, you are also the best, I sincerely thank you for the sisterly affection, help and care!
My brothers, Binggquan, Daozheng, and Jinrui. When I’m with you, I feel very relaxed, even if we don’t say a word. You are very tolerant to me and I hope you didn’t suffer a lot from my talkative style. Brotherly thank you, guys, for being there and wish you all the excellent future!
My international brothers Faizan, Sajad and Zaid. Faizan, you are a calm and determined person, the conversation with you is always full of knowledge. Sajad, you can always maintain an elegant image, we can discuss many topics and find common ground. Zaid, you are optimistic and energetic and have excellent communication skills, and the delicious food you cooked for us impressed me a lot. Guys, you
ACKNOWLEDGEMENTS
251 have taught me a lot about the culture of your own countries and made me more cosmopolitan, open and inclusive. Your understanding, help, and things done together all contributed to a successful last 2 years of my Ph.D.. I am grateful to have all of you alongside me!
Many thanks to our postdoc Shabnam, you are a nice colleague for me and I really enjoyed the huge laughter from you when we talked. My best wishes to you.
Thanks to my Ph.D. colleagues. Fandi, thank you for the yummy Indonesian food and valuable information gave me time to time. Mojgan, thanks for being nice officemate and sharing snacks. Ruixue, Li, Zefeng, Bidong, Qiang, Xin, Xiaofang, it was a pleasure working with you all. Ruixue, special thanks to you for the nice talk when we worked in the same row. Li, thank you for the nice food you cooked for us. Bidong and Zefeng, I am confident that you can conduct very interesting research. Qiang and Xin, I am glad to work with you on ongoing projects, you are very brilliant. Xiaofang, working with Dinos is an enjoyable experience, you are lucky.
My friends and students, Kumchok and Jesse. Both of you, that I was honored to supervise and whom I, also, learned from. I have enjoyed every moment of working with you, it was a fabulous experience. We have done great job together which resulting in several publications. Thank you for still coming to work after the internship period. You two are a big surprise for me and I am pround of you. I wish best of luck for your future!
I am grateful to former members of the lab Yuanze, Natalia, Edwin, Eman, Vishwanatha, Fernando, Ajay, Maryam, Angelina, Angel. It was a pleasure meeting you all. Santosh, my friend, you are helpful and I always remember the trip to Italy together. Thanks to our biology lab colleagues Kai, Wenjia, Chao, Ran, Xiaocheng, and Juliana, for the nice memories. I would like to thank the people from the group of Prof. Dekker, Fangyuan and Zhangping. Fangyuan, thank you for the nice lunch time we had before in Eriba and Zernike. Zhangping, thank you for helpful discussions, you are an excellent friend. I wish, all of you, a bright future.
Many thanks to visiting students that made the lab truly international: Marta F, Federica, Francesca, Sara, Antonio, Miska, Tatiana, Max, Kees, Harmen, Elmar, Perry, Gita, Vincenzo, John, Martin, Danielle, Renan, Frans, Khaled, Robert, Salomão, Oliver (thanks for the great drawing on my fumehood) and many many more, I really had a very good memories with some of you. I would like to thank in particular Paola, Arianna, and Michel, with whom I have great memories from my first year in the lab.
Special thanks to my Chinese friends Haigen, Ji, Yizhou, Keni, Liangliang, Shanshan, Xiaoxuan, Siwei, Deng, Siqi, Guangcai, Dan, Mei, for the wonderful time we spent together in the Netherlands. Haigen, thank you so much for your attention on my work and the helpful discussions.
I will never forget the full support from my former supervisor during my master, Prof. Jian Yang, who was the first to introduce me in the area of organic & medicinal chemistry and has always encouraged me. My dear friends from this lab, Rongqiang, Pin, Yafei, Yufeng, Ji, Yan, Manshuo and Congtao, who are always eager to meet and spend time together.
Finally, to my family, who have always been there for me: I am grateful in more ways than I can express
for your support and encouragement over the years.I dedicate this dissertation to my beloved family. Qian Wang
CONFERENCES
252
Conferences
1. Mendeleev 2019, the XI International Conference on Chemistry for Young Scientists (Saint Petersburg, RU, Sep. 2019). Poster presentation: Pd-Catalyzed De Novo Assembly of Diversely Substituted Indole-Fused Polyheterocycles.
2. 7th International Conference on Multicomponent Reactions and Related Chemistry (Düsseldorf, DE, Aug. 2018). Poster presentation: With Unprotected Amino acids to Tetrazolo Peptidomimetics.
PUBLICATIONS
253
List of Publications
(+co-first author)
1. Q. Wang, J. Tuinhof, K.C. Mgimpatsang,
K. Kurpiewska, J. Kalinowska-Tluscik, A.
Dömling*. Copper-Catalyzed Modular Assembly of Polyheterocycles. J. Org. Chem.
2020, 85, 9915-9927.
2. Q. Wang, K.C. Mgimpatsang, M. Konstantinidou, S.V. Shishkina, A. Dömling*.
1,3,4-Oxadiazoles by Ugi-Tetrazole and Huisgen Reaction. Org. Lett. 2019, 21, 7320-7323.
3. Q. Wang, A. Osipyan, M. Konstantinidou, R. Butera, K.C. Mgimpatsang, S.V. Shishkina, A.
Dömling*. Pd-Catalyzed De Novo Assembly of Diversely Substituted Indole-Fused
Polyheterocycles. J. Org. Chem. 2019, 84, 12148-12156.
4. M. Rudrakshula
+, N. Naveen
+, Y. Wang, Q. Wang, M. Konstantinidou, A. Dömling*. β‐
Carbolinone Analogues from the Ugi Silver Mine. Eur. J. Org. Chem. 2018, 24,
3139-3143.
5. M. Rudrakshula
+, Q. Wang
+, and A. Dömling*. With Unprotected Amino Acids to
Tetrazolo Peptidomimetics. Chem. Comm. 2017, 53, 8549-8552.
Manuscripts under preparation
1. Q. Wang, K.C. Mgimpatsang, A. Dömling*. Isoquinolone-4-Carboxylic Acids by
Ammonia-Ugi-4CR and Copper-Catalyzed Domino Reaction. Org. Lett. Under revision.
2. Q. Wang, A. Dömling*. Ammonia: An Environmentally Friendly Building Block in
Multi-component Reactions. To be submitted soon (review article).
3. Q. Wang
+, Q. Zheng
+, A. Dömling*. Highly N-Substituted Pyroglutamic Acids by
Ugi-5C-3CR. Under preparation.
4. Q. Wang
+, X. Li
+, A. Dömling*. Diversity Oriented Synthesis of Isoquinolones. Under
preparation.
5. M. Konstantinidou, P. Golik, Q. Wang, Z. Wang, B. Zhang, T. Holak, A. Dömling*.
Discovery of Proteolysis Targeting Chimeras for the Cyclin-Dependent Kinases 4 and 6
(CDK4/6). Under preparation.
Master Research
1. Q. Wang, J. Yang*, Y. Zheng, X. Liao. An Alternative Synthesis of
2,6-Dimethoxyl-1,4-Benzoquinone. J. Chem. Res. 2017, 41, 193-194.
2. Q. Wang, X. Liao, C. Xiang, J. Yang*. A Practical Synthesis of the Flavone, Scutellarein. J.
Chem. Res. 2017, 41, 157-159.
3. R. Liao, P. Lv, Q. Wang, J. Zheng, B. Feng, B. Yang*. Cyclodextrin-Based Biological
Stimuli-responsive Carriers for Smart and Precision Medicine. Biomater. Sci. 2017, 5,
1736-1745.
4. Q. Wang, J. Zhang, M. Liu, J. Yang*, X. Zhang, L. Zhou, L. Cao, X. Liao. Modified Syntheses
of the Dietary Flavonoid Luteolin. J. Chem. Res. 2015, 39, 550-552.
5. Q. Wang, J. Yang*, X. Zhang, L.Zhou, X. Liao, B. Yang. Practical Synthesis of Naringenin. J.
Chem. Res. 2015, 39, 455-457.
6. Q. Wang, W. Cui, J. Yang*, B. Yang. Development of A Concise Synthesis of the Flavonoid
Chrysin. J. Chem. Res. 2015, 39, 300-302.
7. Q. Wang, W. Cui, M. Liu, J. Zhang, R. Liao, X. Liao, J. Yang*. An Improved Synthesis of
Apigenin. J. Chem. Res. 2015, 39, 67-69.
我曾经跨过山和大海
255
About the author
Qian Wang was born on the 27th June 1990 in Anhui, China. In July 2013 he graduated with a Bachelor
degree in Pharmacy from Wannan Medical College, China. In June 2016, he earned his Master degree in Pharmaceutical Engineering from Kunming University of Science and Technology under the supervision of Prof. Jian Yang. In the Master program, he was trained as a synthetic organic chemist to handle efficient multiple-step synthesis of naturally occurring bioactive flavonoids. With a strong interest in drug discovery, in the fall of 2016, he moved to The Netherlands to pursue his doctoral degree in the group of Drug Design at the Department of Pharmacy, University of Groningen, under the supervision of Prof. Alexander Dömling. His research interests include multicomponent reaction chemistry and transition metal mediated chemical transformations and PROTAC technology to battle cancer. In his daily life he loves football and pop music, and he draws a lot of strength from the achievements and masterpieces of his idols Cristiano Ronaldo and Pu Shu.
