Design, Synthesis and Biological Evaluation of Novel O2-(2,4-Dinitrophenyl)diazeniumdiolates as Anti-tumor Agents†

doi:10.7503/cjcu20160798

Abstract

Abstract:

O²-(2,4-Dinitrophenyl)diazeniumdiolate(PABA/NO) possesses significant anticancer activity but poor stability. To search for new agents with stronger activity and better stability, PABA/NO was employed as a lead compound. A series of PABA/NO analogues was designed and synthesized with an appropriate secondary amine as the amine moiety in the diazeniumdiolate structure, and replacing the ester bond of the benzene ring with a carbon-nitrogen bond. The structures of the synthesized compounds were characterized by means of ¹H NMR, ¹³C NMR and HRMS. All the target compounds showed strong inhibitory effects against colon cancer HCT-116 cells to a varying extent. Compound 4h(IC₅₀=7.945±0.421 μmol/L) was the most potent against HCT-116 cells, superior to PABA/NO (IC₅₀=12.134±0.675 μmol/L). There was observed that a positive correlation existed between activity and NO release levels. The most active compound 4h released higher levels of NO in colon cancer cells than that in the normal ones. In addition, compound 4h showed better stability in plasma than PABA/NO. These results suggested compound 4h might be a promising anticancer agent, and worthy of further study.

Key words: O2-(2, 4-Dinitrophenyl)diazeniumdiolate, HCT-116 cell, Anti-tumor activity, Stability

CLC Number:

O625

TrendMD:

YAN Chang, ZOU Yu, FU Junjie, HUANG Zhangjian, ZHANG Dayong, ZHANG Yihua. Design, Synthesis and Biological Evaluation of Novel O²-(2,4-Dinitrophenyl)diazeniumdiolates as Anti-tumor Agents^†[J]. Chem. J. Chinese Universities, 2017, 38(4): 591.

Figures/Tables 9

References 20

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Compd.	Appearance	Yield(%)	Chemical formula	m. p./℃	HRMS(calcd. )[M+Na]⁺
2a	Yellow solid	88	C₉H₁₁N₅O₇	149—153	324.0564(324.0556)
2b	Yellow solid	83	C₁₁H₁₃N₅O₇	148—150	350.0721(350.0713)
4a	Yellow solid	68	C₁₄H₂₁N₇O₇	166—171	422.1411(422.1400)
4b	Yellow solid	62	C₁₆H₂₃N₇O₉	155—158	480.1466(480.1455)
4c	Yellow solid	65	C₁₃H₁₈N₆O₈	153—156	409.1093(409.1084)
4d	Yellow solid	68	C₁₄H₂₀N₆O₈	143—147	423.1249(423.1240)
4e	Yellow solid	62	C₁₂H₁₃N₇O₇	145—147	390.0784(390.0774)
4f	Yellow solid	70	C₁₆H₂₃N₇O₇	170—173	448.1566(448.1557)
4g	Yellow solid	69	C₁₈H₂₅N₇O₉	117—119	506.1622(506.1611)
4h	Yellow solid	72	C₁₅H₂₀N₆O₈	146—150	435.1246(435.1240)
4i	Yellow solid	68	C₁₆H₂₂N₆O₈	158—162	449.1407(449.1397)
4j	Yellow solid	71	C₁₄H₁₅N₇O₇	173—176	416.0942(416.0931)

Compd.	Appearance	Yield(%)	Chemical formula	m. p./℃	HRMS(calcd. )[M+Na]⁺
2a	Yellow solid	88	C₉H₁₁N₅O₇	149—153	324.0564(324.0556)
2b	Yellow solid	83	C₁₁H₁₃N₅O₇	148—150	350.0721(350.0713)
4a	Yellow solid	68	C₁₄H₂₁N₇O₇	166—171	422.1411(422.1400)
4b	Yellow solid	62	C₁₆H₂₃N₇O₉	155—158	480.1466(480.1455)
4c	Yellow solid	65	C₁₃H₁₈N₆O₈	153—156	409.1093(409.1084)
4d	Yellow solid	68	C₁₄H₂₀N₆O₈	143—147	423.1249(423.1240)
4e	Yellow solid	62	C₁₂H₁₃N₇O₇	145—147	390.0784(390.0774)
4f	Yellow solid	70	C₁₆H₂₃N₇O₇	170—173	448.1566(448.1557)
4g	Yellow solid	69	C₁₈H₂₅N₇O₉	117—119	506.1622(506.1611)
4h	Yellow solid	72	C₁₅H₂₀N₆O₈	146—150	435.1246(435.1240)
4i	Yellow solid	68	C₁₆H₂₂N₆O₈	158—162	449.1407(449.1397)
4j	Yellow solid	71	C₁₄H₁₅N₇O₇	173—176	416.0942(416.0931)

Compd.	¹H NMR(300 MHz), δ^a	¹³C NMR(75 MHz), δ^b
2a	8.88(s, 1H, ArH), 8.46(d,J=9.24 Hz, 1H, ArH), 7.69(d, J=8.85 Hz, 1H, ArH), 3.82—3.92(m, 4H, NCH₂CH₂OH), 3.41(s, 3H, CH₃)	129.8, 129.2, 122.3, 121.8, 120.5, 117.5, 57.5, 54.8, 39.6
2b	8.89(d,J=2.55 Hz, 1H, ArH), 8.46(dd, J₁=9.3 Hz, J₂=2.64 Hz, 1H, ArH), 7.68(d, J=9.27 Hz, 1H, ArH), 4.03(s, 1H, NCH₂CH₂CHOH), 3.63—3.88(m, 4H, 2×NCH₂CH₂CHOH), 1.84—2.05(m, 4H, 2×NCH₂CH₂CHOH)	152.9, 142.0, 136.8, 129.8, 121.8, 118.0, 63.6, 47.4, 31.8
4a	8.72(s, 1H, ArH), 6.98(s, 1H, ArH), 3.81—3.88(m, 4H, NCH₂CH₂OH), 3.33(s, 3H, CH₃), 3.24—3.27(m, 4H, 2×ArNCH₂CH₂N), 2.58—2.63(m, 4H, 2×ArNCH₂CH₂N), 2.37(s, 3H, CH₃)	153.6, 149.6, 132.2, 127.3, 127.1, 105.4, 57.6, 54.8, 53.9, 50.1, 45.5, 39.6
4b	8.72(s, 1H, ArH), 6.98(s, 1H, ArH), 3.91(t, J=5.1 Hz, 2H, NCH₂CH₂OH), 3.76—3.82(m, 6H, 2×ArNCH₂CH₂N, NCH₂CH₂OH), 3.34(s, 3H, CH₃), 3.31—3.35(m, 7H, 2×ArNCH₂CH₂N, NCH₃), 2.78(s, 2H, CH₂)	170.3, 153.6, 149.6, 132.3, 127.7, 127.2, 105.5, 57.7, 57.6, 54.8, 51.2, 51.1, 50.2, 39.6
4c	8.75(s, 1H, ArH), 6.98(s, 1H, ArH), 3.85—3.89(m, 6H, 2×NCH₂CH₂O, NCH₂CH₂OH), 3.76(t, J=4.71 Hz, 2H, NCH₂CH₂OH), 3.34(s, 3H, CH₃), 3.24(t, J=4.17 Hz, 4H, 2×NCH₂CH₂O)	153.6, 149.6, 132.3, 127.4, 127.2, 105.4, 85.5, 57.6, 54.8, 50.5, 39.6
4d	8.71(s, 1H, ArH), 6.32(s, 1H, ArH), 4.00(s, 2H, NCH₂CH₂OH), 3.87—3.92(m, 3H, NCH₂CH₂OH, NCH₂CH₂CHOH), 3.49(s, 3H, CH₃), 3.34—3.42(m, 4H, 2×NCH₂CH₂CHOH), 1.23—1.28(m, 4H, 2×NCH₂CH₂CHOH)	153.6, 149.8, 131.9, 129.5, 127.4, 107.1, 105.0, 64.9, 64.4, 57.6, 54.8, 48.0, 39.6, 33.5
4e	8.95(s, 1H, ArH), 8.03(s, 1H, Imidazole), 7.86(s, 1H, ArH), 7.52(s, 1H, Imidazole), 7.14(s, 1H, Imidazole), 4.90(s, 1H, OH), 3.75(t, J=5.2 Hz, 2H, NCH₂CH₂OH), 3.63(t, J=4.8 Hz, 2H, NCH₂CH₂OH), 3.14(s, 3H, CH₃)	152.4, 137.6, 136.5, 135.3, 128.5, 124.4, 123.1, 121.0, 116.7, 57.6, 55.5, 54.7
4f	8.73(s, 1H, ArH), 6.96(s, 1H, ArH), 3.51—3.55(m, 4H, 2×ArNCH₂CH₂N), 3.23—3.29(m, 5H, 2×ArNCH₂CH₂N, NCH₂CH₂CHOH), 2.58—2.63(m, 4H, 2×NCH₂CH₂CHOH), 2.37(s, 3H, CH₃), 2.03—2.08(m, 4H, 2×NCH₂CH₂CHOH)	153.0, 149.5, 132.6, 127.4, 127.2, 106.4, 63.7, 53.9, 50.1, 47.4, 45.5, 31.8
4g	8.72(s, 1H, ArH), 6.96(s, 1H, ArH), 3.72(s, 3H, CH₃), 3.29—3.33(m, 5H, 2×ArNCH₂CH₂N, NCH₂CH₂CHOH), 3.22(s, 2H, NCH₂COOMe), 2.63—2.66(m, 8H, 2×NCH₂CH₂CHOH, 2×ArNCH₂CH₂N), 2.02—2.05(m, 4H, 2×NCH₂CH₂CHOH)	170.3, 153.0, 149.5, 132.6, 127.5, 127.2, 106.4, 63.7, 58.3, 57.7, 51.9, 51.2, 50.3, 47.4, 31.8
4h	8.74(s, 1H, ArH), 6.96(s, 1H, ArH), 3.88(t, J=4.5 Hz, 4H, 2×NCH₂CH₂O), 3.81—3.86(m, 1H, NCH₂CH₂CHOH), 3.55—3.58(m, 4H, 2×NCH₂CH₂CHOH), 3.24(t, J=4.38 Hz, 4H, 2×NCH₂CH₂O), 1.84—2.06(m, 4H, 2×NCH₂CH₂CHOH)	150.8, 150.7, 129.9, 127.5, 107.4, 106.3, 66.5, 66.4, 65.1, 51.5, 51.3, 48.4, 47.7, 33.7, 32.1
4i	8.61(s, 1H, ArH), 7.12(s, 1H, ArH), 4.85(s, 2H, 2×OH), 3.75—3.79(m, 2H, 2×NCH₂CH₂CHOH), 3.42—3.45(m, 4H, 2×ArNCH₂CH₂CHOH), 3.12—3.15(m, 4H, 2×NCH₂CH₂CHOH), 1.85—1.88(m, 8H, 4×NCH₂CH₂CHOH)	153.0, 149.6, 132.3, 127.3, 126.9, 106.0, 64.4, 63.7, 48.0, 47.4, 33.4, 31.8
4j	8.95(s, 1H, ArH), 8.05(s, 1H, Imidazole), 7.96(s, 1H, ArH), 7.53(s, 1H, Imidazole), 7.14(s, 1H, Imidazole), 4.85(s, 1H, OH), 3.71(s, 1H, NCH₂CH₂CHOH), 3.44—3.51(m, 4H, 2×NCH₂CH₂CHOH), 1.58—1.85(m, 4H, NCH₂CH₂CHOH)	141.7, 137.6, 134.1, 130.2, 129.3, 128.0, 126.9, 123.9, 120.3, 64.3, 47.8, 33.6

Compd.	¹H NMR(300 MHz), δ^a	¹³C NMR(75 MHz), δ^b
2a	8.88(s, 1H, ArH), 8.46(d,J=9.24 Hz, 1H, ArH), 7.69(d, J=8.85 Hz, 1H, ArH), 3.82—3.92(m, 4H, NCH₂CH₂OH), 3.41(s, 3H, CH₃)	129.8, 129.2, 122.3, 121.8, 120.5, 117.5, 57.5, 54.8, 39.6
2b	8.89(d,J=2.55 Hz, 1H, ArH), 8.46(dd, J₁=9.3 Hz, J₂=2.64 Hz, 1H, ArH), 7.68(d, J=9.27 Hz, 1H, ArH), 4.03(s, 1H, NCH₂CH₂CHOH), 3.63—3.88(m, 4H, 2×NCH₂CH₂CHOH), 1.84—2.05(m, 4H, 2×NCH₂CH₂CHOH)	152.9, 142.0, 136.8, 129.8, 121.8, 118.0, 63.6, 47.4, 31.8
4a	8.72(s, 1H, ArH), 6.98(s, 1H, ArH), 3.81—3.88(m, 4H, NCH₂CH₂OH), 3.33(s, 3H, CH₃), 3.24—3.27(m, 4H, 2×ArNCH₂CH₂N), 2.58—2.63(m, 4H, 2×ArNCH₂CH₂N), 2.37(s, 3H, CH₃)	153.6, 149.6, 132.2, 127.3, 127.1, 105.4, 57.6, 54.8, 53.9, 50.1, 45.5, 39.6
4b	8.72(s, 1H, ArH), 6.98(s, 1H, ArH), 3.91(t, J=5.1 Hz, 2H, NCH₂CH₂OH), 3.76—3.82(m, 6H, 2×ArNCH₂CH₂N, NCH₂CH₂OH), 3.34(s, 3H, CH₃), 3.31—3.35(m, 7H, 2×ArNCH₂CH₂N, NCH₃), 2.78(s, 2H, CH₂)	170.3, 153.6, 149.6, 132.3, 127.7, 127.2, 105.5, 57.7, 57.6, 54.8, 51.2, 51.1, 50.2, 39.6
4c	8.75(s, 1H, ArH), 6.98(s, 1H, ArH), 3.85—3.89(m, 6H, 2×NCH₂CH₂O, NCH₂CH₂OH), 3.76(t, J=4.71 Hz, 2H, NCH₂CH₂OH), 3.34(s, 3H, CH₃), 3.24(t, J=4.17 Hz, 4H, 2×NCH₂CH₂O)	153.6, 149.6, 132.3, 127.4, 127.2, 105.4, 85.5, 57.6, 54.8, 50.5, 39.6
4d	8.71(s, 1H, ArH), 6.32(s, 1H, ArH), 4.00(s, 2H, NCH₂CH₂OH), 3.87—3.92(m, 3H, NCH₂CH₂OH, NCH₂CH₂CHOH), 3.49(s, 3H, CH₃), 3.34—3.42(m, 4H, 2×NCH₂CH₂CHOH), 1.23—1.28(m, 4H, 2×NCH₂CH₂CHOH)	153.6, 149.8, 131.9, 129.5, 127.4, 107.1, 105.0, 64.9, 64.4, 57.6, 54.8, 48.0, 39.6, 33.5
4e	8.95(s, 1H, ArH), 8.03(s, 1H, Imidazole), 7.86(s, 1H, ArH), 7.52(s, 1H, Imidazole), 7.14(s, 1H, Imidazole), 4.90(s, 1H, OH), 3.75(t, J=5.2 Hz, 2H, NCH₂CH₂OH), 3.63(t, J=4.8 Hz, 2H, NCH₂CH₂OH), 3.14(s, 3H, CH₃)	152.4, 137.6, 136.5, 135.3, 128.5, 124.4, 123.1, 121.0, 116.7, 57.6, 55.5, 54.7
4f	8.73(s, 1H, ArH), 6.96(s, 1H, ArH), 3.51—3.55(m, 4H, 2×ArNCH₂CH₂N), 3.23—3.29(m, 5H, 2×ArNCH₂CH₂N, NCH₂CH₂CHOH), 2.58—2.63(m, 4H, 2×NCH₂CH₂CHOH), 2.37(s, 3H, CH₃), 2.03—2.08(m, 4H, 2×NCH₂CH₂CHOH)	153.0, 149.5, 132.6, 127.4, 127.2, 106.4, 63.7, 53.9, 50.1, 47.4, 45.5, 31.8
4g	8.72(s, 1H, ArH), 6.96(s, 1H, ArH), 3.72(s, 3H, CH₃), 3.29—3.33(m, 5H, 2×ArNCH₂CH₂N, NCH₂CH₂CHOH), 3.22(s, 2H, NCH₂COOMe), 2.63—2.66(m, 8H, 2×NCH₂CH₂CHOH, 2×ArNCH₂CH₂N), 2.02—2.05(m, 4H, 2×NCH₂CH₂CHOH)	170.3, 153.0, 149.5, 132.6, 127.5, 127.2, 106.4, 63.7, 58.3, 57.7, 51.9, 51.2, 50.3, 47.4, 31.8
4h	8.74(s, 1H, ArH), 6.96(s, 1H, ArH), 3.88(t, J=4.5 Hz, 4H, 2×NCH₂CH₂O), 3.81—3.86(m, 1H, NCH₂CH₂CHOH), 3.55—3.58(m, 4H, 2×NCH₂CH₂CHOH), 3.24(t, J=4.38 Hz, 4H, 2×NCH₂CH₂O), 1.84—2.06(m, 4H, 2×NCH₂CH₂CHOH)	150.8, 150.7, 129.9, 127.5, 107.4, 106.3, 66.5, 66.4, 65.1, 51.5, 51.3, 48.4, 47.7, 33.7, 32.1
4i	8.61(s, 1H, ArH), 7.12(s, 1H, ArH), 4.85(s, 2H, 2×OH), 3.75—3.79(m, 2H, 2×NCH₂CH₂CHOH), 3.42—3.45(m, 4H, 2×ArNCH₂CH₂CHOH), 3.12—3.15(m, 4H, 2×NCH₂CH₂CHOH), 1.85—1.88(m, 8H, 4×NCH₂CH₂CHOH)	153.0, 149.6, 132.3, 127.3, 126.9, 106.0, 64.4, 63.7, 48.0, 47.4, 33.4, 31.8
4j	8.95(s, 1H, ArH), 8.05(s, 1H, Imidazole), 7.96(s, 1H, ArH), 7.53(s, 1H, Imidazole), 7.14(s, 1H, Imidazole), 4.85(s, 1H, OH), 3.71(s, 1H, NCH₂CH₂CHOH), 3.44—3.51(m, 4H, 2×NCH₂CH₂CHOH), 1.58—1.85(m, 4H, NCH₂CH₂CHOH)	141.7, 137.6, 134.1, 130.2, 129.3, 128.0, 126.9, 123.9, 120.3, 64.3, 47.8, 33.6

Design, Synthesis and Biological Evaluation of Novel O²-(2,4-Dinitrophenyl)diazeniumdiolates as Anti-tumor Agents^†

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[15]	JIANG Yefang, DONG Ru, CAI Xuediao, FENG Jiangshan, LIU Zhike, LIU Shengzhong. Effect of Amphiphilic Quaternary Ammonium Salt Additive on Performance and Stability of Perovskite Solar Cells [J]. Chem. J. Chinese Universities, 2019, 40(8): 1697.