Citation: Xuefeng Wang, Jun Zhang, Qi Chen, Wei Zhou, Jie Wu. Generation of sulfonylureas under photoredox catalysis and their biological evaluations[J]. Chinese Chemical Letters, ;2022, 33(11): 4860-4864. doi: 10.1016/j.cclet.2022.02.025 shu

Generation of sulfonylureas under photoredox catalysis and their biological evaluations

Xuefeng Wang ^{a, b} ,
Jun Zhang ^a ,
Qi Chen ^{a, *,} ,
Wei Zhou ^{b, *,} ,
Jie Wu ^{a, c, d, *,}

a.
Taizhou Central Hospital (Taizhou University Hospital) & School of Pharmaceutical and Materials Engineering, Taizhou University, Taizhou 318000, China
b.
Department of Chemistry, Fudan University, Shanghai 200438, China
c.
State Key Laboratory of Organometallic Chemistry, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, Shanghai 200032, China
d.
School of Chemistry and Chemical Engineering, Henan Normal University, Xinxiang 453007, China

chenq@tzc.edu.cn

zhouw@fudan.edu.cn

jie_wu@fudan.edu.cn

Received Date: 21 December 2021
Revised Date: 9 February 2022
Accepted Date: 10 February 2022
Available Online: 16 February 2022

Figures(8)

Traditional synthesis of sulfonylureas largely depends on nucleophilic addition of arylsulfonamides to pre-synthesized isocyanates. Now we report a new access to alkylsulfonylureas with good yields and broad substrate scope. With the insertion of commercialized chlorosulfonyl isocyanate under photoredox catalysis, alkylsulfonylureas are synthesized in one-pot from the corresponding anilines and silyl enolates. A reaction mechanism is proposed showing the transformation undergoes a radical process, and the practicality of this methodology is proven via application to bioactive molecules. Additionally, the anti-cancer and anti-virus screening of these compounds is evaluated.
- Sulfonylurea,
- Chlorosulfonyl isocyanate,
- Photocatalysis
1. [1]
  R. Turner, Lancet 352 (1998) 837–853. doi: 10.1016/S0140-6736(98)07019-6
2. [2]
  J. Drews, Science 287 (2000) 1960–1964. doi: 10.1126/science.287.5460.1960
3. [3]
  B. Zinman, C. Wanner, J.M. Lachin, et al., N. Engl. J. Med. 373 (2015) 2117–2128. doi: 10.1056/NEJMoa1504720
4. [4]
  A.A. Tahrani, A.H. Barnett, C.J. Bailey, Nat. Rev. Endocrinol. 12 (2016) 566–592. doi: 10.1038/nrendo.2016.86
5. [5]
  A. Loubatières, Ann. N. Y. Acad. Sci. 71 (1957) 192–206. doi: 10.1111/j.1749-6632.1957.tb54591.x
6. [6]
  M. Rendell, Drugs 64 (2004) 1339–1358. doi: 10.2165/00003495-200464120-00006
7. [7]
  W. Lv, X. Wang, Q. Xu, W. Lu, Curr. Top. Med. Chem. 20 (2020) 37–56. doi: 10.2174/1568026620666191224141617
8. [8]
  K.G.M.M. Alberti, P. Zimmet, J. Shaw, Diabet. Med. 23 (2005) 469–480.
9. [9]
  P. Ponikowski, A.A. Voors, S.D. Anker, et al., Eur. Heart J. 37 (2016) 2129–2200. doi: 10.1093/eurheartj/ehw128
10. [10]
  B. Masereel, E. Lohrmann, M. Schynts, et al., J. Pharm. Pharmacol. 44 (1992) 589–593.
11. [11]
  S.E. Kahn, M.E. Cooper, S. Del Prato, Lancet 383 (2014) 1068–1083. doi: 10.1016/S0140-6736(13)62154-6
12. [12]
  D.K. Tanwar, V.R. Surendrabhai, M.S. Gill, Synlett 28 (2017) 2495–2498. doi: 10.1055/s-0036-1590836
13. [13]
  H.G. Peterson, C. Boutin, P.A. Martin, et al., Aquat. Toxicol. 28 (1994) 275–292. doi: 10.1016/0166-445X(94)90038-8
14. [14]
  G. Gece, Corros. Sci. 53 (2011) 3873–3898. doi: 10.1016/j.corsci.2011.08.006
15. [15]
  H.B. Koenig, K.G. Metzger, H.A. Offe, W. Schroeck, Arzneimittel-Forsch 33 (1983) 88–90.
16. [16]
  S. Petersen, Chem. Ber. 83 (1950) 551–554. doi: 10.1002/cber.19500830609
17. [17]
  J. Cervello, T. Sastre, Synthesis (1990) 221–222.
18. [18]
  T. Ventura, V. Zanirato, Eur. J. Org. Chem. (2021) 1201–1214.
19. [19]
  W. Xiao, J. Wu, Chin. Chem. Lett. 32 (2021) 2751–2755. doi: 10.1016/j.cclet.2021.03.033
20. [20]
  I. Butula, V. Vela, M.V. Prostenik, Croat. Chem. Acta 52 (1979) 47–49.
21. [21]
  P. Hebeisen, W. Haap, B. Kuhn, et al., Bioorg. Med. Chem. Lett. 21 (2011) 3237–3242. doi: 10.1016/j.bmcl.2011.04.044
22. [22]
  R. Hunter, A. Msutu, C.L. Dwyer, et al., Synlett 16 (2011) 2335–2338.
23. [23]
  X. Wang, M. Yang, S. Ye, Y. Kuang, J. Wu, Chem. Sci. 12 (2021) 6437–6441. doi: 10.1039/D1SC01351C
24. [24]
  F.S. He, M. Yang, S. Ye, J. Wu, Chin. Chem. Lett. 32 (2021) 461–464. doi: 10.1016/j.cclet.2020.04.043
25. [25]
  K. Zhou, J. Huang, J. Wu, G. Qiu, Chin. Chem. Lett. 32 (2021) 37–39. doi: 10.1016/j.cclet.2020.11.049
26. [26]
  K. Zhou, J. Liu, W. Xie, S. Ye, J. Wu, Chem. Commun. 56 (2020) 2554–2557. doi: 10.1039/D0CC00351D
27. [27]
  X. Gong, M. Yang, J. Liu, et al., Green Chem. 22 (2020) 1906–1910. doi: 10.1039/D0GC00332H
28. [28]
  K. Zhou, J. Chen, J. Wu, Chin. Chem. Lett. 31 (2020) 2996–2998. doi: 10.1016/j.cclet.2020.08.037
29. [29]
  S. Ghosh, S. Samanta, A.K. Ghosh, S. Neogi, A. Hajra, Adv. Synth. Catal. 362 (2020) 4552–4578. doi: 10.1002/adsc.202000647
30. [30]
  M. Yang, H. Han, H. Jiang, et al., Chin. Chem. Lett. 32 (2021) 3535–3538. doi: 10.1016/j.cclet.2021.05.007
31. [31]
  F. He, M. Zhang, M. Zhang, X. Luo, J. Wu, Org. Chem. Front. 8 (2021) 3746–3751. doi: 10.1039/D1QO00556A
32. [32]
  J.K. Rasmussen, A. Hassner, Chem. Rev. 76 (1976) 389–408. doi: 10.1021/cr60301a004
33. [33]
  A. Kamel, P.B. Sattur, Heterocycles 26 (1987) 1051–1076. doi: 10.3987/R-1987-04-1051
34. [34]
  V.I. Gorbatenko, Tetrahedron 49 (1993) 3227–3257. doi: 10.1016/S0040-4020(01)90154-1
35. [35]
  A. Liljeblad, L.T. Kanerva, Tetrahedron 62 (2006) 5831–5854. doi: 10.1016/j.tet.2006.03.109
36. [36]
  B. Furman, K. Borsuk, Z. Kaluza, R. Lysek, M. Chmielewski, Cur. Org. Chem. 8 (2004) 463–473. doi: 10.2174/1385272043485792
37. [37]
  Y. Girard, J.G. Atkinson, J. Rokach, J. Chem. Soc. Perkin Trans. 1 (1979) 1043–1047.
38. [38]
  Y. Zhang, T. Ren, Org. Prep. Proce. Int. 38 (2006) 469–473. doi: 10.1080/00304940609356438
39. [39]
  M. Arnswald, W.P. Neumann, Chem. Ber. 124 (1991) 1997–2000. doi: 10.1002/cber.19911240919
40. [40]
  M. Arnswald, P.N. Wilhelm, J. Org. Chem. 58 (1993) 7022–7028. doi: 10.1021/jo00077a020
41. [41]
  J.A. Picard, P.M. O'Brien, D.R. Sliskovic, et al., J. Med. Chem. 39 (1996) 1243–1252. doi: 10.1021/jm9509455
1. [1]
  Zhen Shi , Wei Jin , Yuhang Sun , Xu Li , Liang Mao , Xiaoyan Cai , Zaizhu Lou . Interface charge separation in Cu2CoSnS4/ZnIn2S4 heterojunction for boosting photocatalytic hydrogen production. Chinese Journal of Structural Chemistry, 2023, 42(12): 100201-100201. doi: 10.1016/j.cjsc.2023.100201
2. [2]
  Qiang Zhang , Weiran Gong , Huinan Che , Bin Liu , Yanhui Ao . S doping induces to promoted spatial separation of charge carriers on carbon nitride for efficiently photocatalytic degradation of atrazine. Chinese Journal of Structural Chemistry, 2023, 42(12): 100205-100205. doi: 10.1016/j.cjsc.2023.100205
3. [3]
  Ziruo Zhou , Wenyu Guo , Tingyu Yang , Dandan Zheng , Yuanxing Fang , Xiahui Lin , Yidong Hou , Guigang Zhang , Sibo Wang . Defect and nanostructure engineering of polymeric carbon nitride for visible-light-driven CO2 reduction. Chinese Journal of Structural Chemistry, 2024, 43(3): 100245-100245. doi: 10.1016/j.cjsc.2024.100245
4. [4]
  Weixu Li , Yuexin Wang , Lin Li , Xinyi Huang , Mengdi Liu , Bo Gui , Xianjun Lang , Cheng Wang . Promoting energy transfer pathway in porphyrin-based sp2 carbon-conjugated covalent organic frameworks for selective photocatalytic oxidation of sulfide. Chinese Journal of Structural Chemistry, 2024, 43(7): 100299-100299. doi: 10.1016/j.cjsc.2024.100299
5. [5]
  Mengjun Zhao , Yuhao Guo , Na Li , Tingjiang Yan . Deciphering the structural evolution and real active ingredients of iron oxides in photocatalytic CO2 hydrogenation. Chinese Journal of Structural Chemistry, 2024, 43(8): 100348-100348. doi: 10.1016/j.cjsc.2024.100348
6. [6]
  Jiangqi Ning , Junhan Huang , Yuhang Liu , Yanlei Chen , Qing Niu , Qingqing Lin , Yajun He , Zheyuan Liu , Yan Yu , Liuyi Li . Alkyl-linked TiO2@COF heterostructure facilitating photocatalytic CO2 reduction by targeted electron transport. Chinese Journal of Structural Chemistry, 2024, 43(12): 100453-100453. doi: 10.1016/j.cjsc.2024.100453
7. [7]
  Jiaqi Ma , Lan Li , Yiming Zhang , Jinjie Qian , Xusheng Wang . Covalent organic frameworks: Synthesis, structures, characterizations and progress of photocatalytic reduction of CO2. Chinese Journal of Structural Chemistry, 2024, 43(12): 100466-100466. doi: 10.1016/j.cjsc.2024.100466
8. [8]
  Yanghanbin Zhang , Dongxiao Wen , Wei Sun , Jiahe Peng , Dezhong Yu , Xin Li , Yang Qu , Jizhou Jiang . State-of-the-art evolution of g-C3N4-based photocatalytic applications: A critical review. Chinese Journal of Structural Chemistry, 2024, 43(12): 100469-100469. doi: 10.1016/j.cjsc.2024.100469
9. [9]
  Tianhao Li , Wenguang Tu , Zhigang Zou . In situ photocatalytically enhanced thermogalvanic cells for electricity and hydrogen production. Chinese Journal of Structural Chemistry, 2024, 43(1): 100195-100195. doi: 10.1016/j.cjsc.2023.100195
10. [10]
  Guixu Pan , Zhiling Xia , Ning Wang , Hejia Sun , Zhaoqi Guo , Yunfeng Li , Xin Li . Preparation of high-efficient donor-π-acceptor system with crystalline g-C3N4 as charge transfer module for enhanced photocatalytic hydrogen evolution. Chinese Journal of Structural Chemistry, 2024, 43(12): 100463-100463. doi: 10.1016/j.cjsc.2024.100463
11. [11]
  Yue Pan , Wenping Si , Yahao Li , Haotian Tan , Ji Liang , Feng Hou . Promoting exciton dissociation by metal ion modification in polymeric carbon nitride for photocatalysis. Chinese Chemical Letters, 2024, 35(12): 109877-. doi: 10.1016/j.cclet.2024.109877
12. [12]
  Jia-Cheng Hou , Wei Cai , Hong-Tao Ji , Li-Juan Ou , Wei-Min He . Recent advances in semi-heterogenous photocatalysis in organic synthesis. Chinese Chemical Letters, 2025, 36(2): 110469-. doi: 10.1016/j.cclet.2024.110469
13. [13]
  Chaoqun Ma , Yuebo Wang , Ning Han , Rongzhen Zhang , Hui Liu , Xiaofeng Sun , Lingbao Xing . Carbon dot-based artificial light-harvesting systems with sequential energy transfer and white light emission for photocatalysis. Chinese Chemical Letters, 2024, 35(4): 108632-. doi: 10.1016/j.cclet.2023.108632
14. [14]
  Jing Wang , Zenghui Li , Xiaoyang Liu , Bochao Su , Honghong Gong , Chao Feng , Guoping Li , Gang He , Bin Rao . Fine-tuning redox ability of arylene-bridged bis(benzimidazolium) for electrochromism and visible-light photocatalysis. Chinese Chemical Letters, 2024, 35(9): 109473-. doi: 10.1016/j.cclet.2023.109473
15. [15]
  Yusong Bi , Rongzhen Zhang , Kaikai Niu , Shengsheng Yu , Hui Liu , Lingbao Xing . Construction of a three-step sequential energy transfer system with selective enhancement of superoxide anion radicals for photocatalysis. Chinese Chemical Letters, 2025, 36(5): 110311-. doi: 10.1016/j.cclet.2024.110311
16. [16]
  Yan Fan , Jiao Tan , Cuijuan Zou , Xuliang Hu , Xing Feng , Xin-Long Ni . Unprecedented stepwise electron transfer and photocatalysis in supramolecular assembly derived hybrid single-layer two-dimensional nanosheets in water. Chinese Chemical Letters, 2025, 36(4): 110101-. doi: 10.1016/j.cclet.2024.110101
17. [17]
  Lihua Ma , Song Guo , Zhi-Ming Zhang , Jin-Zhong Wang , Tong-Bu Lu , Xian-Shun Zeng . Sensitizing photoactive metal–organic frameworks via chromophore for significantly boosting photosynthesis. Chinese Chemical Letters, 2024, 35(5): 108661-. doi: 10.1016/j.cclet.2023.108661
18. [18]
  Zhenchun Yang , Bixiao Guo , Zhenyu Hu , Kun Wang , Jiahao Cui , Lina Li , Chun Hu , Yubao Zhao . Molecular engineering towards dual surface local polarization sites on poly(heptazine imide) framework for boosting H₂O₂ photo-production. Chinese Chemical Letters, 2024, 35(8): 109251-. doi: 10.1016/j.cclet.2023.109251
19. [19]
  Jing-Jing Zhang , Lujun Lou , Rui Lv , Jiahui Chen , Yinlong Li , Guangwei Wu , Lingchao Cai , Steven H. Liang , Zhen Chen . Recent advances in photochemistry for positron emission tomography imaging. Chinese Chemical Letters, 2024, 35(8): 109342-. doi: 10.1016/j.cclet.2023.109342
20. [20]
  Meijuan Chen , Liyun Zhao , Xianjin Shi , Wei Wang , Yu Huang , Lijuan Fu , Lijun Ma . Synthesis of carbon quantum dots decorating Bi₂MoO₆ microspherical heterostructure and its efficient photocatalytic degradation of antibiotic norfloxacin. Chinese Chemical Letters, 2024, 35(8): 109336-. doi: 10.1016/j.cclet.2023.109336

Get Citation

PDF

XML

Metrics

PDF Downloads(23)
Abstract views(969)
HTML views(163)

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