Functionalized Naphthalenes For Diverse Applications

Naphthalene derivatives are substructures of many natural compounds,² synthetic drugs,³ dispersants, and synthetic dyes and pigments.¹ Examples of occurrences and applications of the naphthalene core are given in Figure 1. Compounds 1 and 2 were recently identified as active components of Pentas parvifolia, a plant used in therapy.^2b Nabumetone 3 and Terbinafine 4 are examples of commercialized naphthalene-based drugs, while Mitonafide 5⁴ exhibiting anti-cancer activity is at the clinical trial stage. Naphthalenes are also used in dye industry (e.g., compound 6) and applied research.⁵

Figure 1. Examples of naturally occurring and synthetic functionalized naphthalenes.

In view of a high relevance of the naphthalene moiety in drug discovery and materials development, it is of importance to design novel naphthalene-based building blocks with controllable substitution patterns and variable functional groups. In response to this vivid drug discovery market demand Life Chemicals has produced its original functionalized naphthalenes, with some of their examples being presented below.

The full catalogue of the title structures can be provided upon request at orders@lifechemicals.com

References:

1. Booth, G. Naphthalene Derivatives in ‘Ullmann’s Encyclopedia of Industrial Chemistry’, 2012 Wiley-VCH, Weinheim, vol. 23, p. 671.
2. (a) Chen, W.; Tang, W.; Zhang, R.; Lou, L.; Zhao, W. J. Nat. Prod. 2007, 70, 567–570. (b) Abdissa, N.; Pan, F.; Gruhonjic, A.; Grafenstein, J.; Fitzpatrick, P. A.; Landberg, Rissanen, K.; Yenesew, A.; Erdelyi, M. J. Nat. Prod. 2016, 79, 2181–2187.
3. According to www.drugbank.ca (accessed in March 2019) there are 33 approved naphthalene-derived drugs and 56 investigational compounds.
4. Ingrassia, L.; Lefranc, F.; Kiss, R.; Mijatovic, T. Curr. Med. Chem. 2009, 16, 1192-1213.
5. (a) Rinco, O.; Nolet, M.-C. Ovans, R.; Bohne, C. Photochem. Photobiol. Sci. 2003, 2, 1140–1151. (b) Xu, J.; Dang, D. K.; Tran, V. T.; Liu, X.; Chung, J. S.; Hur, S. H.; Choi, W. M.; Kim, E. J.; Kohl, P. A. J. Coll. Interf. Sci. 2014, 418, 37–42.