Skip to main content

Advertisement

SpringerLink
Log in

Synthesis, structure characterization, and biological evaluation of some new 1,2,3-benzotriazole derivatives

  • Original Research
  • Published:
Medicinal Chemistry Research Aims and scope Submit manuscript

Abstract

Ten novel benzotriazole compounds were synthesized. Their chemical structures were confirmed by 1H NMR, IR, and elemental analyses, coupled with three selected single-crystal structures (compounds A2, B3, and B5). Their antimycotic and antitumor activities were also investigated. The title compounds showed some antitumor activities, especially in the case of A3 and A4, which showed the most potent activity of propagation inhibition in liver and galactophore cancer cells.

This is a preview of subscription content, log in via an institution to check access.

Access this article

Log in via an institution

Price excludes VAT (USA)
Tax calculation will be finalised during checkout.

Instant access to the full article PDF.

Institutional subscriptions

Scheme 1
Fig. 1
Fig. 2
Fig. 3
Fig. 4
Fig. 5
Fig. 6
Fig. 7
Fig. 8

Similar content being viewed by others

References

  • Abonia R, Insuastya B, Quirogaa J, Noguerasb M, Meierc H (2004) Use of β-(N,N-dialkylamino) propiophenones in the synthesis of nitrogenated heterocyclic compounds. Mini Rev Org Chem 1:387–402

    Article  CAS  Google Scholar 

  • Al-Soud YA, Al-Masoudi NA, Ferwanah A (2003) Synthesis and properties of new substituted 1,2,4-triazoles: potential antitumor agents. Bioorg Med Chem 11(8):1701–1708

    Article  CAS  PubMed  Google Scholar 

  • Antonio C, Michele P, Gianpiero B, Bernardetta B, Marta M, Roberta L (2004) Synthesis and antiproliferative activity of 3-aryl-2-[1H(2H)-benzotriazol-1(2)-yl]acrylonitriles variously substituted: Part 4. Il Farmaco 59:637–644

    Article  Google Scholar 

  • Biagi G, Giorgi I, Livi O, Scartoni V, Barili PL, Calderone V (2001) New 5-substituted-1-(2-hydroxybenzoyl)-benzotriazoles, potassium channel activators IV. Il Farmaco 56:827–834

    Article  CAS  PubMed  Google Scholar 

  • Cui YM, Nan FJ (2006) Biological electron emission principle of lead compounds in drug optimization. Chin Bull Life Sci 18:161

    Google Scholar 

  • Emami S, Falahati M, Banifatemi A, Shafiee A (2004) Stereoselective synthesis and antifungal activity of (Z)-trans-3-azolyl-2-methylchromanone oxime ethers. Bioorg Med Chem 12:5881–5889

    Article  CAS  PubMed  Google Scholar 

  • Fang L-Y, Zhang G-S, Li C-L, Zheng X-C, Zhu L-Z, Xiao J-J, Szakacs G, Nadas J, Chan K-K, Wang P-G, Sun D-X (2006) Discovery of a daunorubicin analogue that exhibits potent antitumor activity and overcomes P-gp-mediated drug resistance. J Med Chem 49:932–941

    Article  CAS  PubMed  Google Scholar 

  • Hansen MB, Nielsen SE, Berg K (1989) Re-examination and further development of a precise and rapid dye method for measuring cell growth/cell kill. J Immunol Methods 119:203–210

    Article  CAS  PubMed  Google Scholar 

  • Kasiotis KM, Haroutounian SA (2006) 2-Pyridin-2-yl-1H-indole derivatives: sSynthesis, estrogen receptor binding affinity, and photophysical properties. Bioorg Chem 34:1–14

    Article  CAS  PubMed  Google Scholar 

  • Leonetti F, Favia A, Rao A, Aliano R, Paluszcak A, Hartmann RW, Carotti A (2004) Design, synthesis, and 3D QSAR of novel potent and selective aromatase inhibitors. J Med Chem 47:6792–6803

    Article  CAS  PubMed  Google Scholar 

  • Lin R, Connolly PJ, Huang SL, Wetter SK, Lu YH, Murray WV, Emanuel SL, Gruninger RH, Fuentes-Pesquera AR, Rugg CA, Middleton SA, Jolliffe LK (2005) 1-Acyl-1H-[1,2,4]triazole-3,5-diamine analogues as novel and potent anticancer cyclin-dependent kinase inhibitors: synthesis and evaluation of biological activities. J Med Chem 48:4208–4211

    Article  CAS  PubMed  Google Scholar 

  • McClure KF, Abramov YA, Laird ER, Barberia JT, Cai W, Carty TJ, Cortina SR, Danley DE, Dipesa AJ, Donahue KM, Dombroski MA, Elliott NC, Gabel CA, Han S, Hynes TR, LeMotte PK, Mansour MN, Marr ES, Letavic MA, Pandit J, Ripin DB, Sweeney FJ, Tan D, Tao Y (2005) Theoretical and experimental design of a typical kinase inhibitor: application to p38 MAP kinase. J Med Chem 48:5728–5737

    Article  CAS  PubMed  Google Scholar 

  • Nardelli NJ (1995) PARST95—an update to PARST: a system of Fortran routines for calculating molecular structure parameters from the results of crystal structure analyses. Appl Crystallogr 28:659

    Article  CAS  Google Scholar 

  • Pagliai F, Pirali T, Grosso ED, Brisco RD, Tron GC, Sorba G, Genazzani AA (2006) Rapid synthesis of triazole-modified resveratrol analogues via click chemistry. J Med Chem 49:467–470

    Article  CAS  PubMed  Google Scholar 

  • Saberi MR, Vinh TK, Yee SW, Griffiths BJN, Evans PJ, Simons C (2006) Potent CYP19 (aromatase) 1-[(benzofuran-2-yl)(phenylmethyl)pyridine, -imidazole, and -triazole inhibitors: synthesis and biological evaluation. J Med Chem 49:1016–1022

    Article  CAS  PubMed  Google Scholar 

  • Saüczewski F, Reszka P, Gdaniec M, Grünert R, Bednarski PJ (2004) Synthesis, X-ray crystal structures, stabilities, and in vitro cytotoxic activities of new heteroarylacrylonitriles. J Med Chem 47:3438–3439

    Article  Google Scholar 

  • Scapin G, Patel SB, Becker JW, Wang Q, Desponts C, Waddleton D, Skorey K, Cromlish W, Bayly C, Therien M, Gauthier JY, Li CS, Lau CK, Ramachandran C, Kennedy BP, Asante-Appiah E (2003) The structural basis for the selectivity of benzotriazole inhibitors of PTP1B. Biochemistry 42:11451–11459

    Article  CAS  PubMed  Google Scholar 

  • Semple G, Skinner PJ, Cherrier MC, Webb PJ, Sage CR, Tamura SY, Chen R, Richman JG, Connolly DT (2006) 1-Alkyl-benzotriazole-5-carboxylic acids are highly selective agonists of the human orphan G-protein-coupled receptor GPR109b. J Med Chem 49:1227–1230

    Article  CAS  PubMed  Google Scholar 

  • Sheldrick GM (1996) SADABS program for empirical absorption correction of area detector data. University of Göttingen, Göttingen

    Google Scholar 

  • Sheldrick GM (1997) SHELXTL V51 software reference manual. Bruker AXS, Madison, WI

    Google Scholar 

  • Siemens (1996) SMART and SAINT area detector control and integration software. Siemens Analytical X-Ray Systems, Madison, WI

  • Spek AL (1990) PLATON, an integrated tool for the analysis of the results of a single crystal structure determination. Acta Crystallogr A 46:C34

    Google Scholar 

  • Touami SM, Poon CC, Wender PA (1997) Sequence specific DNA cleavage by conjugates of benzotriazoles and minor groove binders. J Am Chem Soc 119:7611–7612

    Article  CAS  Google Scholar 

  • Wan J, Li CL, Li XM, Zhang SS (2006) Synthesis, structure and biological activities of 2-(1H–1,2,3-benzotriazol-1-yl)-1-(4-methylphenyl)-2-(1H–1, 2, 4-triazol-1-yl)-1-ethanone. Chem Res Chin Univ 22:465–467

    Article  CAS  Google Scholar 

  • Wang YQ, Li LF, Tian ZM, Jiang W, Larrick JW (2006) Synthesis and antitumor activity of CBI-bearing ester and carbamate prodrugs of CC-1065 analogue. Bioorg Med Chem 14:7854–7861

    Article  CAS  PubMed  Google Scholar 

  • Wilson AJ (1992) International tables for X-ray crystallography. Vol C. Kluwer Academic, Dordrecht, Netherlands

    Google Scholar 

  • Xu LZ, Jian FF, Gao HR, Chong CY (2003) Synthesis, structure and biological activities of S-[α-(4-methoxyphenylcarbonyl)-2-(1,2,4-triazole-1-yl)] ethyl-N,N-dimethyldithiocarbamate. Chin J Chem 21:1615–1617

    Article  CAS  Google Scholar 

  • Zhang SS, Wan J, Li CL, Li M, Qu B (2007a) Syntheses and biological activities of novel triazole compounds. J Heterocycl Chem 44:75–78

    Article  CAS  Google Scholar 

  • Zhang SS, Wan J, Li XM, Li CL, Xu LZ (2007b) Syntheses, structure and biological activities of 2-(1H-benzo[1,2,3]triazole-1–y1)-1-(3-methyl-4-bromobipheny1)-2-(1H–1,2,4-triazole-1–y1)ethanon. Chem Res Chin Univ 23:120–122

    Article  CAS  Google Scholar 

Download references

Acknowledgments

This work was supported by the Natural Science Foundation of Shandong Province (Grants Y2007B50 and Y2006B10), Outstanding Adult-Young Scientific Research Encouraging Foundation of Shandong Province (2008BS09017), and Qingdao University of Science and Technology Dr. Seed funding.

Author information

Authors and Affiliations

  1. State Key Laboratory of Pharmaceutical Biotechnology, Nanjing University, Nanjing, Jiangsu, 210093, People’s Republic of China

    Jun Wan & Hai-Liang Zhu

  2. Key Laboratory of Eco-Chemical Engineering, Ministry of Education, and College of Chemistry and Molecular Engineering, Qingdao University of Science and Technology, Qingdao, 266042, People’s Republic of China

    Jun Wan, Xia Yan, Cuiping Ma & Sai Bi

Authors
  1. Jun Wan
    View author publications

    You can also search for this author in PubMed Google Scholar

  2. Xia Yan
    View author publications

    You can also search for this author in PubMed Google Scholar

  3. Cuiping Ma
    View author publications

    You can also search for this author in PubMed Google Scholar

  4. Sai Bi
    View author publications

    You can also search for this author in PubMed Google Scholar

  5. Hai-Liang Zhu
    View author publications

    You can also search for this author in PubMed Google Scholar

Corresponding author

Correspondence to Hai-Liang Zhu.

Rights and permissions

Reprints and permissions

About this article

Cite this article

Wan, J., Yan, X., Ma, C. et al. Synthesis, structure characterization, and biological evaluation of some new 1,2,3-benzotriazole derivatives. Med Chem Res 19, 970–983 (2010). https://doi.org/10.1007/s00044-009-9243-3

Download citation

  • Received:

  • Accepted:

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1007/s00044-009-9243-3

Keywords

Search

Navigation