引用本文:
薛思佳, 申杰峰, 王庆东, 蔡志娟. L-N-(2-噻吩磺酰基)氨基酸乙酯衍生物的合成、结构及抗肿瘤活性[J]. 应用化学,
2008, 25(2): 152-156.
Citation: XUE Si-Jia, SHENG Jie-Feng, WANG Qing-Dong, CAI Zhi-Juan. Synthesis,Crystal Structure and Antitumor Activity of α-L-Amino Acid Ester Derivatives[J]. Chinese Journal of Applied Chemistry, 2008, 25(2): 152-156.
Citation: XUE Si-Jia, SHENG Jie-Feng, WANG Qing-Dong, CAI Zhi-Juan. Synthesis,Crystal Structure and Antitumor Activity of α-L-Amino Acid Ester Derivatives[J]. Chinese Journal of Applied Chemistry, 2008, 25(2): 152-156.
L-N-(2-噻吩磺酰基)氨基酸乙酯衍生物的合成、结构及抗肿瘤活性
摘要:
将2-噻吩磺酰基引入α-L-氨基酸乙酯中,设计合成了9种未见文献报道的新化合物N-2-噻吩磺酰基-α-L-氨基酸乙酯和N-2-噻吩磺酰基甘氨酸乙酯。结构经IR、1H NMR、MS和元素分析测试技术得以确证。对化合物3a的单晶进行了X射线晶体结构测定,结果表明,其属于单斜晶系,Cc空间群,晶胞参数a=1.4538(2)nm,b=0.56902(9)nm,c=1.4337(2)nm,Z=4,V=1.0978(3)nm3,Dc=1.508mg/m3,α=90.00°,β=112.245(2)°,γ=90.00°,F(000)=520,R=0.0858,wR=0.2265。经MTT法多次平行实验观测,结果发现,部分目标化合物对白血病K562细胞的增殖有明显的抑制作用:在质量浓度为1.0×10-8g/mL时,化合物3f、3g、3i对白血病K562肿瘤细胞的增殖有较好的抑制作用,抑制率分别为40.22%、33.47%和31.86%,化合物3a~3i对白血病K562肿瘤细胞的增殖的半数抑制质量浓度(IC50,1×10-6g/mL)依次为:35.65、13.87、9.23、4.9、9.24、8.16、7.84、7.73、7.73、6.57。实验中还发现,部分化合物能够诱导肿瘤细胞自然凋亡。通过与5-氟尿嘧啶(5-FU)阳性对照结果表明,该类化合物具有很好的研究开发潜力和价值。
English
Synthesis,Crystal Structure and Antitumor Activity of α-L-Amino Acid Ester Derivatives
Abstract:
In order to search for new antineoplastic drugs,nine novel N-2-thiophenesulfonyl-α-L-amino-acid esters were synthesized.The structures of the target compounds were determined by means of IR,1H NMR,MS and elemental analysis.The crystal structure of the target compound 3a was determined by X-ray diffraction analysis.Crystal data:Monoclinic,space group:Cc,a=1.453 8(2) nm,b=0.569 02(9) nm,c=1.433 7(2) nm,Z=4,V=1.097 8(3) nm3,Dc=1.508 mg/m3,α=90.00°,β=112.245(2)°,γ=90.00°,F(000)=520,R=0.085 8,wR=0.226 5.Via MTT assay,the inhibitory rate of the title compounds against the K562 Cell Proliferation was measured.The inhibition rate of the compounds(3f,3g,3i) against leukemia K562 cell proliferation were 40.22%,33.47%,and 31.86%,respectively,when the concentration of was 1.0×10-8 g/mL.The IC50 concentration(1×10-6 g/mL) of the compounds(3a~3i) was 35.65,13.87,9.23,4.9,9.24,8.16,7.84,7.73,7.73,and 6.57,respectively.The result of preliminary bioassay shows that some of the target compounds possess antiproliferation effects on K562 cells.Some of the compounds induced cell apoptosis in the experiment.
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Key words:
- synthesis
- / α-L-amino-acid ester
- / K562 cell
- / thiophene-sulfonamide
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