Citation: Qigui Nie, Jie Sun, Xianfu Fang, Xun He, Feng Xiong, Gong Zhang, Yangfeng Li, Yizhou Li. Antimony salt-promoted cyclization facilitating on-DNA syntheses of dihydroquinazolinone derivatives and its applications[J]. Chinese Chemical Letters, ;2023, 34(8): 108132. doi: 10.1016/j.cclet.2023.108132 shu

Antimony salt-promoted cyclization facilitating on-DNA syntheses of dihydroquinazolinone derivatives and its applications

Qigui Nie ^{a, 1} ,
Jie Sun ^{a, 1} ,
Xianfu Fang ^a ,
Xun He ^b ,
Feng Xiong ^b ,
Gong Zhang ^{a, c, *,} ,
Yangfeng Li ^{a, c, *,} ,
Yizhou Li ^{a, c, d, e, *,}

a.
Chongqing Key Laboratory of Natural Product Synthesis and Drug Research, Innovative Drug Research Center, School of Pharmaceutical Sciences, Chongqing University, Chongqing 401331, China
b.
Shenzhen Innovation Center for Small Molecule Drug Discovery Co., Ltd., Shenzhen 518110, China
c.
Chemical Biology Research Center, School of Pharmaceutical Sciences, Chongqing University, Chongqing 401331, China
d.
Key Laboratory of Biorheological Science and Technology, Ministry of Education, College of Bioengineering, Chongqing University, Chongqing 400044, China
e.
Beijing National Laboratory for Molecular Sciences, Beijing 100190, China

gongzhang@cqu.edu.cn

yfli3@cqu.edu.cn

izhouli@cqu.edu.cn

Received Date: 6 November 2022
Revised Date: 26 December 2022
Accepted Date: 2 January 2023
Available Online: 9 January 2023

Figures(5)

DNA-encoded chemical libraries technology has become a novel approach to finding hit compounds in early drug discovery. The chemical space in a DEL would be expanded to realize its full potential, especially when integrating privileged scaffold dihydroquinazoline that has demonstrated a variety of diverse bioactivities. Driven by the requirement of parallel combinatorial synthesis, we here report a facile synthesis of on-DNA dihydroquinazolinone from aldehyde and anthranilamide. This DNA-compatible reaction was promoted by antimony trichloride, which has been proven to accelerate the reaction and improve conversions. Notably, the broad substrate scope of aldehydes and anthranilamides was explored under the mild reaction condition to achieve moderate-to-excellent conversion yields. We further applied the reaction into on-DNA macrocyclization, obtaining macrocycles embedded dihydroquinazolinone scaffold in synthetically useful conversion yields.
- DNA-encoded chemical libraries,
- Antimony,
- Dihydroquinazolinone,
- Macrocyclization,
- DNA-compatible chemistry
1. [1]
  N. Kerru, L. Gummidi, S. Maddila, K.K. Gangu, S.B. Jonnalagadda, Molecules 25 (2020) 1909. doi: 10.3390/molecules25081909
2. [2]
  M. Badolato, F. Aiello, N. Neamati, RSC Adv. 8 (2018) 20894–20921. doi: 10.1039/c8ra02827c
3. [3]
  Y. Nkizinkiko, B.V.S. Suneel Kumar, V.U. Jeankumar, et al., Bioorg. Med. Chem. 23 (2015) 4139–4149. doi: 10.1016/j.bmc.2015.06.063
4. [4]
  J. Zhang, J.W. Zhao, L.P. Wang, et al., Tetrahedron 72 (2016) 936–943. doi: 10.1016/j.tet.2015.12.055
5. [5]
  Z. Xie, J. Lan, H. Zhu, et al., Chin. Chem. Lett. 32 (2021) 1427–1431. doi: 10.1016/j.cclet.2020.09.059
6. [6]
  Y. Huang, L. Meng, Q. Nie, et al., Nat. Chem. 13 (2021) 77–88. doi: 10.1038/s41557-020-00605-x
7. [7]
  M. Song, G.T. Hwang, J. Med. Chem. 63 (2020) 6578–6599. doi: 10.1021/acs.jmedchem.9b01782
8. [8]
  K.D. Hook, J.T. Chambers, R. Hili, Chem. Sci. 8 (2017) 7072–7076. doi: 10.1039/C7SC02779F
9. [9]
  S. Brenner, R.A. Lerner, Proc. Natl. Acad. Sci. USA 89 (1992) 5381–5383. doi: 10.1073/pnas.89.12.5381
10. [10]
  Y.K. Sunkari, V.K. Siripuram, T.L. Nguyen, M. Flajolet, Trends Pharmacol. Sci. 43 (2022) 4–15. doi: 10.1016/j.tips.2021.10.008
11. [11]
  G. Zhao, S. Zhong, G. Zhang, Y. Li, Y. Li, Angew. Chem. Int. Ed. 61 (2022) e202115157. doi: 10.1002/anie.202115157
12. [12]
  G. Zhao, Y. Huang, Y. Zhou, Y. Li, X. Li, Expert Opin. Drug Discovery 14 (2019) 735–753. doi: 10.1080/17460441.2019.1614559
13. [13]
  B. Cai, D. Kim, S. Akhand, et al., J. Am. Chem. Soc. 141 (2019) 17057–17061. doi: 10.1021/jacs.9b08085
14. [14]
  G. Zimmermann, Y. Li, U. Rieder, et al., ChemBioChem 18 (2017) 853–857. doi: 10.1002/cbic.201600637
15. [15]
  C. Zambaldo, J.P. Daguer, J. Saarbach, S. Barluenga, N. Winssinger, Med. Chem. Commun. 7 (2016) 1340–1351. doi: 10.1039/C6MD00242K
16. [16]
  F.V. Reddavide, W. Lin, S. Lehnert, Y. Zhang, Angew. Chem. Int. Ed. 54 (2015) 7924–7928. doi: 10.1002/anie.201501775
17. [17]
  L.M. McGregor, T. Jain, D.R. Liu, J. Am. Chem. Soc. 136 (2014) 3264–3270. doi: 10.1021/ja412934t
18. [18]
  P.A. Harris, S.B. Berger, J.U. Jeong, et al., J. Med. Chem. 60 (2017) 1247–1261. doi: 10.1021/acs.jmedchem.6b01751
19. [19]
  H.A. Stanway-Gordon, J.S. Graham, M.J. Waring, Angew. Chem. Int. Ed. 61 (2022) e202111927. doi: 10.1002/anie.202111927
20. [20]
  M.K. Skopic, F. Losch, A.E. McMillan, et al., Org. Lett. 24 (2022) 1383–1387. doi: 10.1021/acs.orglett.2c00228
21. [21]
  F. Ma, J. Li, S.N. Zhang, et al., ACS Catal. 12 (2022) 1639–1649. doi: 10.1021/acscatal.1c05338
22. [22]
  X. Fu, J. Tang, R. Hua, et al., Org. Lett. 24 (2022) 2208–2213. doi: 10.1021/acs.orglett.2c00516
23. [23]
  B. Lin, W. Lu, Z.Y. Chen, et al., Org. Lett. 23 (2021) 7381–7385. doi: 10.1021/acs.orglett.1c02562
24. [24]
  Z. Fan, S. Zhao, T. Liu, et al., Chem. Sci. 11 (2020) 12282–12288. doi: 10.1039/d0sc03935g
25. [25]
  S.O. Badir, J. Sim, K. Billings, et al., Org. Lett. 22 (2020) 1046–1051. doi: 10.1021/acs.orglett.9b04568
26. [26]
  J. Sun, Q. Nie, X. Fang, et al., Org. Biomol. Chem. 20 (2022) 5045–5049. doi: 10.1039/d2ob00862a
27. [27]
  E. Lenci, L. Baldini, A. Trabocchi, Bioorg. Med. Chem. 41 (2021) 116218. doi: 10.1016/j.bmc.2021.116218
28. [28]
  R. Wu, S. Gao, T. Du, et al., Chem. Asian J. 15 (2020) 4033–4037. doi: 10.1002/asia.202001105
29. [29]
  C.J. Gerry, S.L. Schreiber, Curr. Opin. Chem. Biol. 56 (2020) 1–9.
30. [30]
  R.M. Franzini, C. Randolph, J. Med. Chem. 59 (2016) 6629–6644. doi: 10.1021/acs.jmedchem.5b01874
31. [31]
  Y. Gao, G. Zhao, P. He, et al., Bioconjugate Chem. 33 (2022) 105–110. doi: 10.1021/acs.bioconjchem.1c00567
32. [32]
  P.R. Fitzgerald, B.M. Paegel, Chem. Rev. 121 (2021) 7155–7177. doi: 10.1021/acs.chemrev.0c00789
33. [33]
  D.K. Kolmel, A.S. Ratnayake, M.E. Flanagan, et al., Org. Lett. 22 (2020) 2908–2913. doi: 10.1021/acs.orglett.0c00574
34. [34]
  Y. Li, R. De Luca, S. Cazzamalli, et al., Nat. Chem., 10 (2018) 441–448. doi: 10.1038/s41557-018-0017-8
35. [35]
  A.W. Dombrowski, A.L. Aguirre, A. Shrestha, K.A. Sarris, Y. Wang, J. Org. Chem. 87 (2022) 1880–1897. doi: 10.1021/acs.joc.1c01427
36. [36]
  L. Fan, C.P. Davie, ChemBioChem 18 (2017) 843–847. doi: 10.1002/cbic.201600563
37. [37]
  S.A. Pourmousavi, A. Kanaani, H.R. Fatahi, F. Ghorbani, D. Ajloo, J. Phys. Chem. Solids 106 (2017) 82–93. doi: 10.1016/j.jpcs.2017.03.008
38. [38]
  J. Chai, X. Lu, C.C. Arico-Muendel, Y. Ding, M.P. Pollastri, Bioconjugate Chem. 32 (2021) 1973–1978. doi: 10.1021/acs.bioconjchem.1c00363
39. [39]
  S. Yang, G. Zhao, Y. Gao, et al., Chem. Sci. 13 (2022) 2604–2613. doi: 10.1039/d1sc06268a
40. [40]
  X. Li, Z.J. Gartner, B.N. Tse, D.R. Liu, J. Am. Chem. Soc. 126 (2004) 5090–5092. doi: 10.1021/ja049666+
41. [41]
  X. Fang, Y. Wang, P. He, et al., Org. Lett. 24 (2022) 3291–3296. doi: 10.1021/acs.orglett.2c01187
42. [42]
  A.L. Satz, J. Cai, Y. Chen, et al., Bioconjugate Chem. 26 (2015) 1623–1632. doi: 10.1021/acs.bioconjchem.5b00239
43. [43]
  Y. Gao, Y. Sun, G. Zhao, et al., Org. Lett. (2022) 6664–6669. doi: 10.1021/acs.orglett.2c02714
44. [44]
  B.D. Rupnar, T.R. Kachave, P.D. Jawale, S.U. Shisodia, R.P. Pawar, J. Iran. Chem. Soc. 14 (2017) 1853–1858. doi: 10.1007/s13738-017-1124-y
45. [45]
  C.J. Gerry, M.J. Wawer, P.A. Clemons, S.L. Schreiber, J. Am. Chem. Soc. 141 (2019) 10225–10235. doi: 10.1021/jacs.9b01203
46. [46]
  S. Zhong, X. Fang, Y. Wang, et al., Org. Lett. 24 (2022) 1022–1026. doi: 10.1021/acs.orglett.1c04169
47. [47]
  Q. Liang, J.Y. He, X. Zhao, et al., J. Med. Chem. 64 (2021) 4196–4205. doi: 10.1021/acs.jmedchem.1c00123
48. [48]
  Y. Bao, Y. Yan, K. Xu, et al., J. Org. Chem. 80 (2015) 4736–4742. doi: 10.1021/acs.joc.5b00191
49. [49]
  A.A. Peterson, A.M. Rangwala, M.K. Thakur, et al., Nat. Chem. Biol. 18 (2022) 1184–1195. doi: 10.1038/s41589-022-01116-1
50. [50]
  J.P. Maianti, A. McFedries, Z.H. Foda, et al., Nature 511 (2014) 94–98. doi: 10.1038/nature13297
51. [51]
  L. Plais, J. Scheuermann, RSC Chem. Biol. 3 (2022) 7–17. doi: 10.1039/d1cb00161b
52. [52]
  C.J. Stress, B. Sauter, L.A. Schneider, T. Sharpe, D. Gillingham, Angew. Chem. Int. Ed. 58 (2019) 9570–9574. doi: 10.1002/anie.201902513
53. [53]
  Y. Onda, G. Bassi, A. Elsayed, et al., Chem. Eur. J. 27 (2021) 7160–7167. doi: 10.1002/chem.202005423
54. [54]
  M.H. Shin, K.J. Lee, H.S. Lim, Bioconjugate Chem. 30 (2019) 2931–2938. doi: 10.1021/acs.bioconjchem.9b00628
55. [55]
  Z. Zhu, A. Shaginian, L.C. Grady, et al., ACS Chem. Biol. 13 (2018) 53–59. doi: 10.1021/acschembio.7b00852
56. [56]
  W.H. Connors, S.P. Hale, N.K. Terrett, Curr. Opin. Chem. Biol. 26 (2015) 42–47. doi: 10.1016/j.cbpa.2015.02.004
57. [57]
  Z.J. Gartner, B.N. Tse, R. Grubina, et al., Science 305 (2004) 1601–1605. doi: 10.1126/science.1102629
58. [58]
  O.B.C. Monty, P. Nyshadham, K.M. Bohren, et al., ACS Comb. Sci. 22 (2020) 80–88. doi: 10.1021/acscombsci.9b00199
59. [59]
  X. Lu, L. Fan, C.B. Phelps, C.P. Davie, C.P. Donahue, Bioconjugate Chem. 28 (2017) 1625–1629. doi: 10.1021/acs.bioconjchem.7b00292
60. [60]
  Q.G. Nie, S. Zhong, Y. Li, G. Zhang, Y. Li, Chin. Chem. Lett. 33 (2022) 2559–2563. doi: 10.1016/j.cclet.2021.09.041
61. [61]
  Q. Nie, X. Fang, C. Liu, et al., J. Org. Chem., 87 (2022) 2551–2558. doi: 10.1021/acs.joc.1c02496
62. [62]
  E. Koesema, A. Roy, N.G. Paciaroni, et al., Angew. Chem. Int. Ed., 61 (2022) e202116999. doi: 10.1002/anie.202116999
63. [63]
  P. Yang, X. Wang, B. Li, et al., Chem. Sci. 12 (2021) 5804–5810. doi: 10.1039/d1sc00789k
64. [64]
  M.V. Pham, M. Bergeron-Brlek, C. Heinis, ChemBioChem 21 (2020) 543–549. doi: 10.1002/cbic.201900390
65. [65]
  L.R. Malins, J.N. deGruyter, K.J. Robbins, et al., J. Am. Chem. Soc., 139 (2017) 5233–5241. doi: 10.1021/jacs.7b01624
66. [66]
  J. Shan, X. Ling, J. Liu, X. Wang, X. Lu, Bioorg. Med. Chem. 42 (2021) 116234. doi: 10.1016/j.bmc.2021.116234
1. [1]
  Chang Liu , Tao Wu , Lijiao Deng , Xuzi Li , Xin Fu , Shuzhen Liao , Wenjie Ma , Guoqiang Zou , Hai Yang . Programmed DNA walkers for biosensors. Chinese Chemical Letters, 2024, 35(9): 109307-. doi: 10.1016/j.cclet.2023.109307
2. [2]
  Xiaoxia WANG , Ya'nan GUO , Feng SU , Chun HAN , Long SUN . Synthesis, structure, and electrocatalytic oxygen reduction reaction properties of metal antimony-based chalcogenide clusters. Chinese Journal of Inorganic Chemistry, 2024, 40(6): 1201-1208. doi: 10.11862/CJIC.20230478
3. [3]
  Jia-Li Xie , Tian-Jin Xie , Yu-Jie Luo , Kai Mao , Cheng-Zhi Huang , Yuan-Fang Li , Shu-Jun Zhen . Octopus-like DNA nanostructure coupled with graphene oxide enhanced fluorescence anisotropy for hepatitis B virus DNA detection. Chinese Chemical Letters, 2024, 35(6): 109137-. doi: 10.1016/j.cclet.2023.109137
4. [4]
  Pu Zhang , Xiang Mao , Xuehua Dong , Ling Huang , Liling Cao , Daojiang Gao , Guohong Zou . Two UV organic-inorganic hybrid antimony-based materials with superior optical performance derived from cation-anion synergetic interactions. Chinese Chemical Letters, 2024, 35(9): 109235-. doi: 10.1016/j.cclet.2023.109235
5. [5]
  Yang Qin , Jiangtian Li , Xuehao Zhang , Kaixuan Wan , Heao Zhang , Feiyang Huang , Limei Wang , Hongxun Wang , Longjie Li , Xianjin Xiao . Toeless and reversible DNA strand displacement based on Hoogsteen-bond triplex. Chinese Chemical Letters, 2024, 35(5): 108826-. doi: 10.1016/j.cclet.2023.108826
6. [6]
  Xiaohong Wen , Mei Yang , Lie Li , Mingmin Huang , Wei Cui , Suping Li , Haiyan Chen , Chen Li , Qiuping Guo . Enzymatically controlled DNA tetrahedron nanoprobes for specific imaging of ATP in tumor. Chinese Chemical Letters, 2024, 35(8): 109291-. doi: 10.1016/j.cclet.2023.109291
7. [7]
  Jingwen Zhao , Jianpu Tang , Zhen Cui , Limin Liu , Dayong Yang , Chi Yao . A DNA micro-complex containing polyaptamer for exosome separation and wound healing. Chinese Chemical Letters, 2024, 35(9): 109303-. doi: 10.1016/j.cclet.2023.109303
8. [8]
  Tian Feng , Yun-Ling Gao , Di Hu , Ke-Yu Yuan , Shu-Yi Gu , Yao-Hua Gu , Si-Yu Yu , Jun Xiong , Yu-Qi Feng , Jie Wang , Bi-Feng Yuan . Chronic sleep deprivation induces alterations in DNA and RNA modifications by liquid chromatography-mass spectrometry analysis. Chinese Chemical Letters, 2024, 35(8): 109259-. doi: 10.1016/j.cclet.2023.109259
9. [9]
  Zhe-Han Yang , Jie Yin , Lei Xin , Yuanfang Li , Yijie Huang , Ruo Yuan , Ying Zhuo . Research advancement of DNA-based intelligent hydrogels: Manufacture, characteristics, application of disease diagnosis and treatment. Chinese Chemical Letters, 2024, 35(10): 109558-. doi: 10.1016/j.cclet.2024.109558
10. [10]
  Wei Chen , Pieter Cnudde . A minireview to ketene chemistry in zeolite catalysis. Chinese Journal of Structural Chemistry, 2024, 43(11): 100412-100412. doi: 10.1016/j.cjsc.2024.100412
11. [11]
  Peiwen Liu , Fang Zhao , Jing Zhang , Yunpeng Bai , Jinxing Ye , Bo Bao , Xinggui Zhou , Li Zhang , Changlu Zhou , Xinhai Yu , Peng Zuo , Jianye Xia , Lian Cen , Yangyang Yang , Guoyue Shi , Lin Xu , Weiping Zhu , Yufang Xu , Xuhong Qian . Micro/nano flow chemistry by Beyond Limits Manufacturing. Chinese Chemical Letters, 2024, 35(5): 109020-. doi: 10.1016/j.cclet.2023.109020
12. [12]
  Yingxiao Zong , Yangfei Wei , Xiaoqing Liu , Junke Wang , Huanfang Guo , Junli Wang , Zhuangzhi Shi , Tao Tu , Cheng Yang , Chongyang Wang , Leyong Wang . The 4^th CCL Organic Chemistry Forum held in Zhangye. Chinese Chemical Letters, 2024, 35(8): 109743-. doi: 10.1016/j.cclet.2024.109743
13. [13]
  Haiying Lu , Weijie Li . The electrolyte solvation and interfacial chemistry for anode-free sodium metal batteries. Chinese Journal of Structural Chemistry, 2024, 43(11): 100334-100334. doi: 10.1016/j.cjsc.2024.100334
14. [14]
  Xiumei LI , Yanju HUANG , Bo LIU , Yaru PAN . Syntheses, crystal structures, and quantum chemistry calculation of two Ni(Ⅱ) coordination polymers. Chinese Journal of Inorganic Chemistry, 2024, 40(10): 2031-2039. doi: 10.11862/CJIC.20240109
15. [15]
  Xueling Yu , Lixing Fu , Tong Wang , Zhixin Liu , Na Niu , Ligang Chen . Multivariate chemical analysis: From sensors to sensor arrays. Chinese Chemical Letters, 2024, 35(7): 109167-. doi: 10.1016/j.cclet.2023.109167
16. [16]
  Min Fu , Pan He , Sen Zhou , Wenqiang Liu , Bo Ma , Shiying Shang , Yaohao Li , Ruihan Wang , Zhongping Tan . An unexpected stereochemical effect of thio-substituted Asp in native chemical ligation. Chinese Chemical Letters, 2024, 35(8): 109434-. doi: 10.1016/j.cclet.2023.109434
17. [17]
  Xianxu Chu , Lu Wang , Junru Li , Hui Xu . Surface chemical microenvironment engineering of catalysts by organic molecules for boosting electrocatalytic reaction. Chinese Chemical Letters, 2024, 35(8): 109105-. doi: 10.1016/j.cclet.2023.109105
18. [18]
  Xu-Hui Yue , Xiang-Wen Zhang , Hui-Min He , Lei Qiao , Zhong-Ming Sun . Synthesis, chemical bonding and reactivity of new medium-sized polyarsenides. Chinese Chemical Letters, 2024, 35(7): 108907-. doi: 10.1016/j.cclet.2023.108907
19. [19]
  Ying Li , Long-Jie Wang , Yong-Kang Zhou , Jun Liang , Bin Xiao , Ji-Shen Zheng . An improved installation of 2-hydroxy-4-methoxybenzyl (iHmb) method for chemical protein synthesis. Chinese Chemical Letters, 2024, 35(5): 109033-. doi: 10.1016/j.cclet.2023.109033
20. [20]
  Min Huang , Ru Cheng , Shuai Wen , Liangtong Li , Jie Gao , Xiaohui Zhao , Chunmei Li , Hongyan Zou , Jian Wang . Ultrasensitive detection of microRNA-21 in human serum based on the confinement effect enhanced chemical etching of gold nanorods. Chinese Chemical Letters, 2024, 35(9): 109379-. doi: 10.1016/j.cclet.2023.109379

Get Citation

PDF

XML

Metrics

PDF Downloads(3)
Abstract views(152)
HTML views(3)

通讯作者: 陈斌, bchen63@163.com

1.
沈阳化工大学材料科学与工程学院沈阳 110142