阿替韦啶

阿替韦啶
	IUPAC名; {4-[3-(Ethylamino)pyridin-2-yl]piperazin-1-yl}(5-methoxy-1H-indol-2-yl)methanone
识别
CAS号	136816-75-6
PubChem	60848
ChemSpider	54835
SMILES	O=C(N2CCN(c1ncccc1NCC)CC2)c4cc3cc(OC)ccc3[nH]4;
InChI	1/C21H25N5O2/c1-3-22-18-5-4-8-23-20(18)25-9-11-26(12-10-25)21(27)19-14-15-13-16(28-2)6-7-17(15)24-19/h4-8,13-14,22,24H,3,9-12H2,1-2H3;
InChIKey	UCPOMLWZWRTIAA-UHFFFAOYAK
性质
化学式	C21H25N5O2
摩尔质量	379.46 g/mol g·mol⁻¹
	若非注明，所有数据均出自标准状态（25 ℃，100 kPa）下。

阿替韦啶（INN：Atevirdine）是一种非核苷逆转录酶抑制剂，已被研究用于治疗 HIV。^[1]

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合成

制备吡啶基哌嗪结构始于将2-氯-3-硝基吡啶的氯原子通过哌嗪进行芳香族取代反应，得到3。然后，将该化合物与焦碳酸二叔丁酯反应得到4。随后，通过催化氢化将硝基团还原。在氰基硼氢化锂存在下，通过乙醛进行还原烷基化反应得到相应的N-乙基衍生物。通过与三氟乙酸反应可除去保护基。将得到的胺与5-甲氧基-3-吲哚乙酸的咪唑衍生物反应，生成了阿替韦啶。

参见

地拉韦啶

参考资料

[1]
Morse GD, Reichman RC, Fischl MA, et al. Concentration-targeted phase I trials of atevirdine mesylate in patients with HIV infection: dosage requirements and pharmacokinetic studies. The ACTG 187 and 199 study teams. Antiviral Res. January 2000, 45 (1): 47–58. PMID 10774589. doi:10.1016/S0166-3542(99)00073-X.
[2]
D. L. Romero, Drugs Future 19, 9 (1995).
[3]
WO 9109849,Romero, Donna Lee; Mark Allen Mitchell & Richard Charles Thomas et al.,“Diaromatic substituted anti-AIDS compounds”,发表于1991-07-11
[4]
Romero, D. L.; Morge, R. A.; Biles, C.; Berrios-Pena, N.; May, P. D.; Palmer, J. R.; Johnson, P. D.; Smith, H. W.; Busso, M.; et al. Discovery, Synthesis, and Bioactivity of Bis(heteroaryl)piperazines. 1. A Novel Class of Non-Nucleoside HIV-1 Reverse Transcriptase Inhibitors. Journal of Medicinal Chemistry. 1994, 37 (7): 999–1014. PMID 7512142. doi:10.1021/jm00033a018.

[pmid10774589-1] [1]
Morse GD, Reichman RC, Fischl MA, et al. Concentration-targeted phase I trials of atevirdine mesylate in patients with HIV infection: dosage requirements and pharmacokinetic studies. The ACTG 187 and 199 study teams. Antiviral Res. January 2000, 45 (1): 47–58. PMID 10774589. doi:10.1016/S0166-3542(99)00073-X.

[2] [2]
D. L. Romero, Drugs Future 19, 9 (1995).

[3] [3]
WO 9109849,Romero, Donna Lee; Mark Allen Mitchell & Richard Charles Thomas et al.,“Diaromatic substituted anti-AIDS compounds”,发表于1991-07-11

[4] [4]
Romero, D. L.; Morge, R. A.; Biles, C.; Berrios-Pena, N.; May, P. D.; Palmer, J. R.; Johnson, P. D.; Smith, H. W.; Busso, M.; et al. Discovery, Synthesis, and Bioactivity of Bis(heteroaryl)piperazines. 1. A Novel Class of Non-Nucleoside HIV-1 Reverse Transcriptase Inhibitors. Journal of Medicinal Chemistry. 1994, 37 (7): 999–1014. PMID 7512142. doi:10.1021/jm00033a018.

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