Antibacterial and Insecticidal Activities of the Revived Azoanthrols

References

• (a) Chunmei Gao, Derong Cao, Sheyang Xu and Herbert Meier. “Acid-catalyzed cyclization of anthracenol derivatives to homotriptycenes.” J. Org. Chem. 71 (2006): 3071–3076. (b) Hans-Gert Korth and Peter Mulder. “Anthrone and related hydroxyarenes: tautomerization and hydrogen bonding.” J. Org. Chem. 78 (2013): 7674–7682 (references cited therein).
   PubMed Web of Science ®Google Scholar
• Madhubabu Alaparthi, Kadarkaraisamy Mariappan, Eric Dufek, Mariah Hoffmana and Andrew G. Sykes. “A new detection mechanism involving keto–enol tautomerization: selective fluorescence detection of Al(III) by dehydration of secondary alcohols in mixed DMSO/aqueous media.” RSC Adv. 2016, 6, 11295–11302.
   Web of Science ®Google Scholar
• Francesco Fringuelli and Aldo Taticchi. The Diels-Alder Reaction: Selected Practical Methods, Chapter 1, (John Wiley & Sons, 2002), 1–25.
   Google Scholar
• (a) Jun Kumagaia, Teppei Otsuki, U. V. Subba Reddy, Yoshihito Kohari, Chigusa Seki, Koji Uwai, Yuko Okuyama, Eunsang Kwon, Michio Tokiwa, Mitsuhiro Takeshita, et al. “Chiral primary amino alcohol organobase catalysts for the asymmetric Diels–Alder reactions of anthrones with maleimides.” Tetrahedron Asymm. 26 (2015): 1423–1429. (b) Ummareddy Venkata Subba Reddy, Madhu Chennapuram, Chigusa Seki, Eunsang Kwon, Yuko Okuyama and Hiroto Nakano. “Catalytic efficiency of primary β-amino alcohols and their derivatives in organocatalysis.” Eur. J. Org. Chem. 2016 (2016): 4124–4143. (c) Trupti S. Tawde, Swapnil J. Wagh, Jai V. Sapre, Vaibhav N. Khose, Purav M. Badani and Anil V. Karnik. “Reversal of enantioselectivity induced by the achiral part of an organocatalyst in a Diels–Alder reaction.” Tetrahedron Asymm. 27 (2016): 130–135.
   Google Scholar
• (a) Huaili Zhao, Mingyan Xiao, Lubin Xu, Liang Wang and Jian Xiao. “Bifunctional thiourea catalyzed asymmetric Michael addition of anthrone to methyleneindolinones.” RSC Adv. 6 (2016): 38558–38562. (b) Hong-Wei Sun, Yu-Hua Liao, Zhi-Jun Wu, Hao-Yu Wang, Xiao-Mei Zhang and Wei-Cheng Yuan. “Enantioselective 1,6-Michael addition of anthrone to 3-methyl-4-nitro-5-alkenyl-isoxazoles catalyzed by bifunctional thiourea-tertiary amines.” Tetrahedron 67 (2011): 3991–3996. (c) Jędrzej Wysocki, Marcin Kwit and Jacek Gawronski. “Absolute configuration determination and convenient asymmetric synthesis of cis-3-(9-Anthryl)cyclohexanol with proline as a catalyst.” CHIRALITY 24 (2012): 833–839.
   Web of Science ®Google Scholar
• (a) Charles C. J. Loh, Xiang Fang, Brendan Peters and Mark Lautens. “Benzylic functionalization of anthrones via the asymmetric ring opening of oxabicycles utilizing a fourth-generation rhodium catalytic system.” Chem. Eur. J. 21 (2015): 13883–13887. (b) Zheng-Le Zhao, Qing Gu, Xin-Yan Wua and Shu-Li You. “Enantioselective synthesis of 10-allylanthrones via iridium-catalyzed allylic substitution reaction.” Chin. Chem. Lett. 27 (2016): 619–622.
   PubMed Web of Science ®Google Scholar
• See for example: Vincent E. Turula, Thomas Gore, Suddham Singh, and Rasappa G. Arumugham. “Automation of the anthrone assay for carbohydrate concentration determinations.” Anal. Chem. 82 (2010): 1786–1792.
   PubMed Web of Science ®Google Scholar
• (a) Yasuhito Koyama, Ryo Yamaguchi and Keisuke Suzuki. “Total synthesis and structure assignment of the anthrone C-glycoside Cassialoin.” Angew. Chem. Int. Ed. 47 (2008): 1084–1087. (b) Kristen J. Procko, Hui Li, and Stephen F. Martin. “Approach toward the total synthesis of 5-hydroxyaloin A.” Org. Lett. 12 (2010): 5632–5635.
   PubMed Web of Science ®Google Scholar
• (a) Tyler Paz Korman, Jason M. Crawford, Jason W. Labonte, Adam G. Newman, Justin Wong, Craig A. Townsend and Shiou-Chuan Tsai. “Structure and function of an iterative polyketide synthase thioesterase domain catalyzing Claisen cyclization in aflatoxin biosynthesis.” PNAS 107 (2010): 6246–6251. (b) Jason M. Crawford, Tyler P. Korman, Jason W. Labonte, Anna L. Vagstad, Eric A. Hill, Oliver Kamari-Bidkorpeh, Shiou-Chuan Tsai and Craig A. Townsend. “Structural basis for biosynthetic programming of fungal aromatic polyketide cyclization.” Nature 461 (2009): 1139–1143. (c) Kenneth C. Ehrlich, Ping Li, Leslie Scharfenstein, and Perng-Kuang Chang. “HypC, the anthrone oxidase involved in aflatoxin biosynthesis.” Appl. Environ. Microbiol. 76 (2010): 3374–3377.
   PubMed Web of Science ®Google Scholar
• See for example: Ulrich Kratz, Helge Prinz and Klaus Müller. “Synthesis and biological evaluation of novel 10-benzyl-substituted 4,5-dichloro-10H-anthracen-9-ones as inhibitors of keratinocyte hyperproliferation.” Eur. J. Med. Chem. 45 (2010): 5278–5285.
   PubMed Web of Science ®Google Scholar
• (a) Yoshiyuki Kimura, Maho Sumiyoshi, Masahiko Taniguchi and Kimiye Baba. “Antitumor and antimetastatic actions of anthrone-C-glucoside, cassialoin isolated from cassia garrettiana heartwood in colon 26-bearing mice.” Cancer Sci. 99 (2008): 2336–2348. (b) Sharnelle S. Phifer, Dongho Lee, Eun-Kyoung Seo, Nam-Cheol Kim, Tyler N. Graf, David J. Kroll, Hernán A. Navarro, Robert A. Izydore, Francisco Jiménez, Ricardo Garcia, et al. “Alvaradoins E-N, antitumor and cytotoxic anthracenone C-glycosides from the leaves of alvaradoa haitiensis.” J. Nat. Prod. 70 (2007): 954–961.
   PubMed Web of Science ®Google Scholar
• Yan Cui, Qing Ye, Heya Wang, Yingchao Li, Xiuhua Xia, Weirong Yao and He Qian. “Aloin protects against chronic alcoholic liver injury via attenuating lipid accumulation, oxidative stress and inflammation in mice.” Archives of Pharmacal Research. 37 (2014): 1624–1633 (references cited therein).
   PubMed Web of Science ®Google Scholar
• Guido Flaminia, Serena Catalano, Chiara Caponi, Lirio Panizzi and Ivano Morelli. “Three anthrones from rubus ulmifolius.” Phytochemistry 59 (2002): 873–876.
   PubMed Web of Science ®Google Scholar
• (a) Klaus Muller, Peter Leukel, Klaus K. Mayerand and Wolfgang Wiegrebe. “Modification of DNA bases by anthralin and related compounds.” Biochem. Pharmacol. 49 (1995): 1607–1613. (References cited therein). (b) Wing Man Lau, Alex W. White and Charles M. Heard. “Topical delivery of a naproxen-dithranol co-drug: In vitro skin penetration, permeation, and staining.” Pharm Res. 27 (2010): 2734–2742 (References cited therein).
   PubMed Web of Science ®Google Scholar
• (a) Klaus Müller, Reinhold Altmann and Helge Prinz. “2-Arylalkyl-substituted anthracenones as inhibitors of 12-lipoxygenase enzymes. 1. Structure–activity relationships of the terminal aryl ring.” Eur. J. Med. Chem. 36 (2001): 569–575. (b) Klaus Müller, Reinhold Altmann and Helge Prinz. “2-Arylalkyl-substituted anthracenones as inhibitors of 12-lipoxygenase enzymes. 2. Structure–activity relationships of the linker chain.” Eur. J. Med. Chem. 37 (2002): 83–89.
   PubMed Web of Science ®Google Scholar
• See for example: (a) Klaus Müller, Hans Reindl and Ingo Gawlik. “10-Hydrocinnamoyl- and 10-cinnamoyl-l,8-dihydroxy-9(10H)-anthracenones as inhibitors of leukotriene B4 biosynthesis and HaCaT cell growth.” Eur. J. Med. Chem. 33 (1998): 969–973. (b) Klaus Müller, Reinhold Altmann and Helge Prinz. “10-Benzoyl-l,8-dihydroxy-9(10H)-anthracenones: Synthesis and biological properties.” Eur. J. Med. Chem. 33 (1998): 209–214.
   Web of Science ®Google Scholar
• Helge Prinz, Peter Schmidt, Konrad J. Böhm, Silke Baasner, Klaus Müller, Eberhard Unger, Matthias Gerlach and Eckhard G. Günther. “10-(2-oxo-2-Phenylethylidene)-10H-anthracen-9-ones as highly active antimicrotubule agents: Synthesis, antiproliferative activity, and inhibition of tubulin polymerization.” J. Med. Chem. 52 (2009): 1284–1294.
   PubMed Web of Science ®Google Scholar
• Ann G. Motten, Robert H. Sik, Colin F. Chignell, and Patrick J. Hayden. “An EPR study of free radicals formed by antipsoriatic and tumor-promoting 9-anthrones in nonpolar solvents.” Chem. Res. Toxicol. 7 (1994): 877–881.
   PubMed Web of Science ®Google Scholar
• (a) Zhuangzhi Shi and Frank Glorius. “Synthesis of Fluorenones via Quaternary Ammonium Salt-Promoted Intramolecular Dehydrogenative Arylation of Aldehydes.” Chem. Sci. 4 (2013): 829–833. (b) Yamaguchi Masahiko, Hasebe Koichi, Uchida Minoru, Higashi Hirofumi and Minami Toru. “An oxidation dimerization of anthrones by oxygen-metal acetate system.” Bull. Chem. Soc. Jpn. 62 (1989): 2745–2747.
   Web of Science ®Google Scholar
• Clinical and Laboratory Standards Institute. Methods for Dilution Antimicrobial Susceptibility Tests for Bacteria That Grow Aerobically; Approved Standard M7-A9, CLSI, Pennsylvania, USA, 2012.
   Google Scholar
• A. W. Bauer, W. M. Kirby, J. C. Sherris and M. Turck. “Antibiotic susceptibility testing by a standardized single disk method.” Am. J. Clin. Pathol. 45 (1966): 493–496.
   PubMed Web of Science ®Google Scholar
• M. J. Chacko, P. K. Bhat, L. V. A. Rao, M. B. D. Singh, E. P. Ramanarayan and K. Sreedharan. “The use of the lady bird beetle, Cryptolaemus montrouzieri for the control of coffee mealy bugs.” Journal of coffee research 8 (1978): 14–19.
   Google Scholar
• (a) P. Ball and C. H. Nicholls. “Azo-hydrazone tautomerism of hydroxyazo compounds-A review.” Dyes Pigm. 3 (1982): 5–26. (b) V. Bekárek, J. Dobáš, J. Socha, P. Vetešník and M. Večeřa. “Reactivity of organic azo-compounds. X. NMR study on azo-hydrazone tautomeric equilibrium in hydroxylazo-compounds.” Coll. Czech. Chem. Commun. 35 (1970): 1406–1414. (c) J. E. Kuder. “HMO consideration of factors affecting tautomerism in hydroxyaryazo compounds.” Tetrahedron 28 (1972): 1973–1981. (d) P. F. Gordon and P. Gregory. Organic Chemistry in Colour, Chapter 3 (Springer-Verlag Berlin Heidelberg, 1987), 95–99.
   Web of Science ®Google Scholar
• See for example: Stefan Bräse. “Privileged Scaffolds,” in Medicinal Chemistry Design, Synthesis, Evaluation, RSC Drug Discovery Series No. 50, the Royal Society of Chemistry 2016.
   Google Scholar
• (a) Zeynep Gültekin, Elghareeb E. Elboray, Moustafa F. Aly, Hussien H. Abbas-Temirek, Helena J. Shepherd and Ronald Grigg. “Participation of compact planar 1,3,5-tri (buta-2,3-dien-1-yl)-1,3,5-triazinane-2,4,6-trione in Pd (0) catalysed seven component cascade reactions delivers novel tunable molecular architecture.” Tetrahedron 70 (2014): 4934–4941. (b) Elghareeb E. Elboray, Moustafa F. Aly, Hussien H. Abbas-Temirek, Gwydion H. Churchill and Ronald Grigg. “Regio and stereoselective catalytic five-component cascades of diverse heterocyclic bisallenes: tri-directional exploration of biochemical space.” Tetrahedron 70 (2014): 110–122. (c) Ronald Grigg, Sunisa Akkarasamiyo, Nutthawat Chuanopparat, Elghareeb E. Elboray, Moustafa F. Aly, Hussien H. Abbas-Temirek, Boonsong Kongkathip and Ngampong Kongkathip. “Stereoselective Pd (0) catalysed five component cascade synthesis of complex Z, Z-bisallylamines.” Chem. Commun. 49 (2013): 2007–2009. (d) Ronald Grigg, Elghareeb E. Elboray, Moustafa F. Aly and Hussien H. Abbas-Temirek. “Exploiting adamantane as a versatile organic tecton: multicomponent catalytic cascade reactions.” Chem. Commun. 48 (2012): 11504–11506.
   Google Scholar
• See for example: (a) H. M. Rageh, S. A. Ibrahim, M. A. Selim and H. M. Alsoghier. “Spectroscopic and semiempirical investigation of the structural features of hetarylazo-5-isoxazolones tautomerism.” J. Saudi Chem. Soc. 21 (2017): S467–S474. (b) Y. H. Ebead. “The role of the medium on the acid dissociation constants of some azo dyes in view of experimental and theoretical data.” J. Mol. Struct. 982 (2010): 100–106.
   Web of Science ®Google Scholar
• See for example: M. A. Rauf, S. Hisaindee and N. Saleh. “Spectroscopic studies of keto-enol tautomeric equilibrium of azo dyes.” RSC Adv. 5 (2015): 18097–18110.
   Web of Science ®Google Scholar
• (a) B. R. Bartlett and D. W. Clancy. “The Comstock Mealybug in California and Observations on Some of Its Natural Enemies.” J. Econ. Entomol. 65 (1972): 1329–1332, DOI: 10.1093/jee/65.5.1329. (b) S. L. Poe. “Treatment for the control of root mealybug on nursery plants.” J. Econ. Entomol. 65 (1972): 241–242.
   Web of Science ®Google Scholar
• (a) G. H. Mohamed, Suzan, A. Badr and S. M. El-Amir. “The efficiency of different materials for controlling vine mealybug, Planococcus ficus (Signoret) (Hemiptera: Pseudococcidae) on grapes during the period of investigation.” Egypt. Acad. J. Biolog. Sci. 4 (2012): 69–75. (b) Mohammed Abul Monjur Khan. “Efficacy of insect growth regulator Buprofezin against Papaya mealybug.” J. Entomol. Zool. Stud. 4 (2016): 730–733.
   Google Scholar
• (a) T. Rudramuni, K. M. Srinivas Reddy and C. T. Ashok Kumar. “Bio-efficacy of new insecticidal molecules against insect-pests of cotton.” Journal of Farm Sciences 1 (2011): 49–58. (b) Shaon Kumar Das. “Mode of action of pesticides and the novel trends–A critical review.” Int. Res. J. Agric. Sci. Soil Sci. 3 (2013): 393–401.
   Google Scholar
• See for example: (a) David Greenwood. “Sulfonamides,” in Antibiotic and chemotherapy, edited by Roger G. Finch, David Greenwood, S. Sagnar Norrby and Richard J. Whitley, chapter 29, 9th ed (Elsevier: Saunders; 2010), 337–343.
   Google Scholar