Chinese Journal of Organic Chemistry ›› 2022, Vol. 42 ›› Issue (2): 543-556.DOI: 10.6023/cjoc202107002 Previous Articles Next Articles
ARTICLES
曾艳a,b, 聂礼飞a, 牛超a, 阿依提拉•麦麦提江a,b, Khurshed Bozorova, 赵江瑜a, 阿吉艾克拜尔•艾萨a,b,*(
)
收稿日期:2021-07-02
修回日期:2021-09-06
发布日期:2022-02-24
通讯作者:
阿吉艾克拜尔•艾萨
基金资助:
Yan Zenga,b, Lifei Niea, Chao Niua, Aytilla Mamatjana,b, Khurshed Bozorova, Jiangyu Zhaoa, Haji Akber Aisaa,b()
Received:2021-07-02
Revised:2021-09-06
Published:2022-02-24
Contact:
Haji Akber Aisa
Supported by:Share
Yan Zeng, Lifei Nie, Chao Niu, Aytilla Mamatjan, Khurshed Bozorov, Jiangyu Zhao, Haji Akber Aisa. Synthesis and Biological Activities of Dihydrooxazolo[5,4-d]-pyrrolo[1,2-a]pyrimidinones[J]. Chinese Journal of Organic Chemistry, 2022, 42(2): 543-556.
| Entry | POCl3/equiv. | Solvent (dry) | Temp./℃ | Yield/% |
|---|---|---|---|---|
| 1 | 2 | DCM | Reflux | — |
| 2 | 2 | DCE | Reflux | 54 |
| 3 | 2 | THF | Reflux | — |
| 4 | 2 | CH3CN | Reflux | — |
| 5 | 2 | CH3OH | Reflux | — |
| 6 | 2 | PhCH3 | Reflux | 51 |
| 7 | 2 | 1,4-Dioxane | Reflux | 67 |
| 8 | 1 | 1,4-Dioxane | Reflux | 48 |
| 9 | 3 | 1,4-Dioxane | Reflux | 73 |
| 10 | 5 | 1,4-Dioxane | Reflux | 71 |
| 11 | 3 | 1,4-Dioxane | 20 | 34 |
| 12 | 3 | 1,4-Dioxane | 40 | 38 |
| 13 | 3 | 1,4-Dioxane | 60 | 56 |
| 14 | 3 | 1,4-Dioxane | 80 | 82 |
| 15 | 3 | 1,4-Dioxane | 100 | 79 |
| Entry | POCl3/equiv. | Solvent (dry) | Temp./℃ | Yield/% |
|---|---|---|---|---|
| 1 | 2 | DCM | Reflux | — |
| 2 | 2 | DCE | Reflux | 54 |
| 3 | 2 | THF | Reflux | — |
| 4 | 2 | CH3CN | Reflux | — |
| 5 | 2 | CH3OH | Reflux | — |
| 6 | 2 | PhCH3 | Reflux | 51 |
| 7 | 2 | 1,4-Dioxane | Reflux | 67 |
| 8 | 1 | 1,4-Dioxane | Reflux | 48 |
| 9 | 3 | 1,4-Dioxane | Reflux | 73 |
| 10 | 5 | 1,4-Dioxane | Reflux | 71 |
| 11 | 3 | 1,4-Dioxane | 20 | 34 |
| 12 | 3 | 1,4-Dioxane | 40 | 38 |
| 13 | 3 | 1,4-Dioxane | 60 | 56 |
| 14 | 3 | 1,4-Dioxane | 80 | 82 |
| 15 | 3 | 1,4-Dioxane | 100 | 79 |
| Compd. | R | IC50/(μmol•L–1) | Diameter of antibacterial cycle/mm | |||||||||||||
|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Hela | MCF-7 | A549 | C.a.a | E.c.b | S.a.c | |||||||||||
| E1 | C2H5 | >50 | >50 | >50 | — | — | — | |||||||||
| E2 | C3H7 | >50 | >50 | >50 | — | — | — | |||||||||
| E3 | C4H9 | >50 | >50 | >50 | — | — | — | |||||||||
| E4 | C12H25 | 43.61±7.34 | >50 | >50 | — | — | — | |||||||||
| E5 | C(CH3)3 | >50 | >50 | >50 | — | — | — | |||||||||
| E6 | AdH | >50 | >50 | >50 | 9 | 10.5 | 10 | |||||||||
| E7 | CH2Ph | >50 | >50 | >50 | 9 | — | — | |||||||||
| E8 | C2H4Ph | 31.44±0.1 | >50 | >50 | 10 | — | — | |||||||||
| E9 | Cp | 30.94±0.7 | >50 | >50 | — | — | — | |||||||||
| E10 | Cy | >50 | >50 | >50 | — | — | — | |||||||||
| E11 | Thiophen-2 | 48.7±0.1 | >50 | >50 | — | — | — | |||||||||
| E12 | Naphth-1 | 4.59±0.10 | >50 | 18.66±0.1 | — | — | — | |||||||||
| E13 | Naphth-2 | 34.82±0.2 | >50 | >50 | — | — | — | |||||||||
| E14 | Biphenyl-4 | >50 | >50 | 18.40±0.1 | — | — | — | |||||||||
| E15 | Furan-2 | >50 | >50 | >50 | — | — | — | |||||||||
| E16 | THP-4 | >50 | >50 | >50 | — | — | — | |||||||||
| E17 | 2-CH3C6H4 | >50 | 43.42±4.99 | >50 | — | — | — | |||||||||
| E18 | 3-CH3C6H4 | >50 | >50 | >50 | 8.5 | — | — | |||||||||
| E19 | 4-CH3C6H4 | 13.46±0.41 | 19.34±3.84 | >50 | — | — | — | |||||||||
| E20 | 2-ClC6H4 | >50 | >50 | >50 | 13 | — | — | |||||||||
| E21 | 3-ClC6H4 | >50 | >50 | >50 | 8.5 | — | — | |||||||||
| Compd. | R | IC50/(μmol•L–1) | Diameter of antibacterial cycle/mm | |||||||||||||
| Hela | MCF-7 | A549 | C.a.a | E.c.b | S.a.c | |||||||||||
| E22 | 4-ClC6H4 | >50 | >50 | >50 | 8.5 | — | — | |||||||||
| E23 | 2-BrC6H4 | >50 | >50 | >50 | — | — | — | |||||||||
| E24 | 3-BrC6H4 | >50 | >50 | >50 | — | — | — | |||||||||
| E25 | 4-BrC6H4 | >50 | >50 | >50 | — | — | 9 | |||||||||
| E26 | 3,5-Me2C6H3 | >50 | >50 | >50 | — | 11 | — | |||||||||
| E27 | 3,4-Cl2C6H3 | >50 | >50 | >50 | 9 | 14 | — | |||||||||
| E28 | 3,5-Cl2C6H3 | >50 | >50 | >50 | 10 | 10 | 9.5 | |||||||||
| E29 | 2,6-Cl2C6H3 | >50 | >50 | >50 | — | — | — | |||||||||
| E30 | 2-FC6H4 | >50 | >50 | >50 | — | 11 | — | |||||||||
| E31 | 3-FC6H4 | >50 | >50 | >50 | — | — | — | |||||||||
| E32 | 4-F C6H4 | >50 | >50 | >50 | — | — | — | |||||||||
| E33 | 3,5-F2C6H3 | >50 | >50 | >50 | — | — | 8 | |||||||||
| E34 | 2,6-F2C6H3 | >50 | >50 | >50 | — | 10 | — | |||||||||
| E35 | 3-CF3C6H4 | 36.86±4.48 | >50 | >50 | — | — | — | |||||||||
| E36 | 4-CF3C6H4 | 42.17±0.85 | >50 | >50 | — | — | — | |||||||||
| E37 | 3,5-(CF3)2C6H3 | >50 | >50 | >50 | — | 10 | 9.5 | |||||||||
| E38 | 3-CF3OC6H4 | >50 | >50 | >50 | — | 10 | — | |||||||||
| E39 | 4-CF3OC6H4 | >50 | 6.89±1.26 | >50 | — | 10 | — | |||||||||
| E40 | 4-(CH3)3CC6H4 | >50 | 30.28±9.66 | >50 | — | 10 | — | |||||||||
| DMSOd | NDe | ND | ND | |||||||||||||
| 调零f | ND | ND | ND | |||||||||||||
| DOX | 0.23±0.15 | 0.15±0.01 | 0.34±0.03 | |||||||||||||
| CPT | 1.32±0.08 | 3.47±0.11 | 0.81±0.14 | |||||||||||||
| 氨苄青霉素 | 11.5g | |||||||||||||||
| 氨苄青霉素 | 10h | |||||||||||||||
| 两性霉素B | 14i | |||||||||||||||
| Compd. | R | IC50/(μmol•L–1) | Diameter of antibacterial cycle/mm | |||||||||||||
|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Hela | MCF-7 | A549 | C.a.a | E.c.b | S.a.c | |||||||||||
| E1 | C2H5 | >50 | >50 | >50 | — | — | — | |||||||||
| E2 | C3H7 | >50 | >50 | >50 | — | — | — | |||||||||
| E3 | C4H9 | >50 | >50 | >50 | — | — | — | |||||||||
| E4 | C12H25 | 43.61±7.34 | >50 | >50 | — | — | — | |||||||||
| E5 | C(CH3)3 | >50 | >50 | >50 | — | — | — | |||||||||
| E6 | AdH | >50 | >50 | >50 | 9 | 10.5 | 10 | |||||||||
| E7 | CH2Ph | >50 | >50 | >50 | 9 | — | — | |||||||||
| E8 | C2H4Ph | 31.44±0.1 | >50 | >50 | 10 | — | — | |||||||||
| E9 | Cp | 30.94±0.7 | >50 | >50 | — | — | — | |||||||||
| E10 | Cy | >50 | >50 | >50 | — | — | — | |||||||||
| E11 | Thiophen-2 | 48.7±0.1 | >50 | >50 | — | — | — | |||||||||
| E12 | Naphth-1 | 4.59±0.10 | >50 | 18.66±0.1 | — | — | — | |||||||||
| E13 | Naphth-2 | 34.82±0.2 | >50 | >50 | — | — | — | |||||||||
| E14 | Biphenyl-4 | >50 | >50 | 18.40±0.1 | — | — | — | |||||||||
| E15 | Furan-2 | >50 | >50 | >50 | — | — | — | |||||||||
| E16 | THP-4 | >50 | >50 | >50 | — | — | — | |||||||||
| E17 | 2-CH3C6H4 | >50 | 43.42±4.99 | >50 | — | — | — | |||||||||
| E18 | 3-CH3C6H4 | >50 | >50 | >50 | 8.5 | — | — | |||||||||
| E19 | 4-CH3C6H4 | 13.46±0.41 | 19.34±3.84 | >50 | — | — | — | |||||||||
| E20 | 2-ClC6H4 | >50 | >50 | >50 | 13 | — | — | |||||||||
| E21 | 3-ClC6H4 | >50 | >50 | >50 | 8.5 | — | — | |||||||||
| Compd. | R | IC50/(μmol•L–1) | Diameter of antibacterial cycle/mm | |||||||||||||
| Hela | MCF-7 | A549 | C.a.a | E.c.b | S.a.c | |||||||||||
| E22 | 4-ClC6H4 | >50 | >50 | >50 | 8.5 | — | — | |||||||||
| E23 | 2-BrC6H4 | >50 | >50 | >50 | — | — | — | |||||||||
| E24 | 3-BrC6H4 | >50 | >50 | >50 | — | — | — | |||||||||
| E25 | 4-BrC6H4 | >50 | >50 | >50 | — | — | 9 | |||||||||
| E26 | 3,5-Me2C6H3 | >50 | >50 | >50 | — | 11 | — | |||||||||
| E27 | 3,4-Cl2C6H3 | >50 | >50 | >50 | 9 | 14 | — | |||||||||
| E28 | 3,5-Cl2C6H3 | >50 | >50 | >50 | 10 | 10 | 9.5 | |||||||||
| E29 | 2,6-Cl2C6H3 | >50 | >50 | >50 | — | — | — | |||||||||
| E30 | 2-FC6H4 | >50 | >50 | >50 | — | 11 | — | |||||||||
| E31 | 3-FC6H4 | >50 | >50 | >50 | — | — | — | |||||||||
| E32 | 4-F C6H4 | >50 | >50 | >50 | — | — | — | |||||||||
| E33 | 3,5-F2C6H3 | >50 | >50 | >50 | — | — | 8 | |||||||||
| E34 | 2,6-F2C6H3 | >50 | >50 | >50 | — | 10 | — | |||||||||
| E35 | 3-CF3C6H4 | 36.86±4.48 | >50 | >50 | — | — | — | |||||||||
| E36 | 4-CF3C6H4 | 42.17±0.85 | >50 | >50 | — | — | — | |||||||||
| E37 | 3,5-(CF3)2C6H3 | >50 | >50 | >50 | — | 10 | 9.5 | |||||||||
| E38 | 3-CF3OC6H4 | >50 | >50 | >50 | — | 10 | — | |||||||||
| E39 | 4-CF3OC6H4 | >50 | 6.89±1.26 | >50 | — | 10 | — | |||||||||
| E40 | 4-(CH3)3CC6H4 | >50 | 30.28±9.66 | >50 | — | 10 | — | |||||||||
| DMSOd | NDe | ND | ND | |||||||||||||
| 调零f | ND | ND | ND | |||||||||||||
| DOX | 0.23±0.15 | 0.15±0.01 | 0.34±0.03 | |||||||||||||
| CPT | 1.32±0.08 | 3.47±0.11 | 0.81±0.14 | |||||||||||||
| 氨苄青霉素 | 11.5g | |||||||||||||||
| 氨苄青霉素 | 10h | |||||||||||||||
| 两性霉素B | 14i | |||||||||||||||
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