azulenes

Summary

Summary: Compounds based on a seven-membered ring fused to a five-membered ring. Heat can rearrange them to NAPHTHALENES which have two fused six-membered rings. They are similar to guaiazulenes which are SESQUITERPENES with a six-membered ring fused to a five-membered ring.

Top Publications

  1. Calabrese C, Almassy R, Barton S, Batey M, Calvert A, Canan Koch S, et al. Anticancer chemosensitization and radiosensitization by the novel poly(ADP-ribose) polymerase-1 inhibitor AG14361. J Natl Cancer Inst. 2004;96:56-67 pubmed
    ..AG14361 is, to our knowledge, the first high-potency PARP-1 inhibitor with the specificity and in vivo activity to enhance chemotherapy and radiation therapy of human cancer. ..
  2. Aumüller I, Yli Kauhaluoma J. Synthesis and tautomerization of benzo[cd]azulen-3-ones. Org Lett. 2011;13:1670-3 pubmed publisher
    ..Furthermore, the facile four-step syntheses of the benzo[cd]azulen-3-ones, the starting materials for the tautomerization reactions, and computational analyses of the tautomerization reaction are included. ..
  3. Veuger S, Curtin N, Richardson C, Smith G, Durkacz B. Radiosensitization and DNA repair inhibition by the combined use of novel inhibitors of DNA-dependent protein kinase and poly(ADP-ribose) polymerase-1. Cancer Res. 2003;63:6008-15 pubmed
    ..Thus, individually, or in combination, the DNA-PK and PARP-1 inhibitors act as potent radiosensitizers and show potential as tools for anticancer therapeutic intervention. ..
  4. Aumüller I, Yli Kauhaluoma J. Benzo[cd]azulene skeleton: azulene, heptafulvene, and tropone derivatives. Org Lett. 2009;11:5363-5 pubmed publisher
    Due to our interest in protein kinase modulating compounds, we developed syntheses for benzo[cd]azulenes. By using very common catalysts and reagents, such as t-BuOK, HCl, and mCPBA, the commercially available guaiazulene is converted in ..
  5. Troncoso C, Perez C, Hernandez V, Sanchez Olate M, Ríos D, San Martin A, et al. Induction of defensive response in Eucalyptus globulus plants and its persistence in vegetative propagation. Nat Prod Commun. 2013;8:397-400 pubmed
  6. Zhao L, Bruneau C, Doucet H. A straightforward access to guaiazulene derivatives using palladium-catalysed sp2 or sp3 C-H bond functionalisation. Chem Commun (Camb). 2013;49:5598-600 pubmed publisher
  7. Akatsu Y, Ohshima N, Yamagishi Y, Nishishiro M, Wakabayashi H, Kurihara T, et al. Apoptosis-inducing activity of trihaloacetylazulenes against human oral tumor cell lines. Anticancer Res. 2006;26:1917-23 pubmed
    ..None of the 26 compounds showed anti-HIV activity. These results suggest [5b] and [11b] as possible candidates for future cancer chemotherapy. ..
  8. Ramadan M, Goeters S, Watzer B, Krause E, Lohmann K, Bauer R, et al. Chamazulene carboxylic acid and matricin: a natural profen and its natural prodrug, identified through similarity to synthetic drug substances. J Nat Prod. 2006;69:1041-5 pubmed
    ..Intriguingly, the biological activity of the natural compound 1 was found because of its similarity to fully synthetic drug substances. This is the reverse process of the common lead function of natural compounds in drug discovery. ..
  9. Skov L, Petersen M, Broman S, Bond A, Nielsen M. New synthetic route to substituted dihydroazulene photoswitches. Org Biomol Chem. 2011;9:6498-501 pubmed publisher
    ..Light-induced ring-opening to the corresponding vinylheptafulvene and the thermal back-reaction was studied in detail. ..

More Information

Publications62

  1. Ishihara M, Wakabayashi H, Motohashi N, Sakagami H. Estimation of relationship between the structure of trihaloacetylazulene derivatives determined by a semiempirical molecular-orbital method (PM5) and their cytotoxicity. Anticancer Res. 2010;30:837-41 pubmed
    ..The descriptors determined by the present method are useful in evaluating the biological activity of trihaloacetylazulenes. ..
  2. Belayev L, Becker D, Alonso O, Liu Y, Busto R, Ley J, et al. Stilbazulenyl nitrone, a novel azulenyl nitrone antioxidant: improved neurological deficit and reduced contusion size after traumatic brain injury in rats. J Neurosurg. 2002;96:1077-83 pubmed
    ..Azulenyl nitrones appear to represent a promising class of neuroprotective agents for combating this devastating condition. ..
  3. Rueeger H, Gerspacher M, Buehlmayer P, Rigollier P, Yamaguchi Y, Schmidlin T, et al. Discovery and SAR of potent, orally available and brain-penetrable 5,6-dihydro-4H-3-thia-1-aza-benzo[e]azulen- and 4,5-dihydro-6-oxa-3-thia-1-aza-benzo[e]azulen derivatives as neuropeptide Y Y5 receptor antagonists. Bioorg Med Chem Lett. 2004;14:2451-7 pubmed
    ..Both classes of compounds are capable of delivering potent and selective orally and centrally bioavailable NPY Y5 receptor antagonists. ..
  4. Löber S, Hubner H, Buschauer A, Sanna F, Argiolas A, Melis M, et al. Novel azulene derivatives for the treatment of erectile dysfunction. Bioorg Med Chem Lett. 2012;22:7151-4 pubmed publisher
    ..Applying an in vivo animal model, test compound 11 turned out to stimulate penile erection in male rats with superior potency in low concentrations when compared to apomorphine. ..
  5. Ma Y, Aisha H, Liao L, Aibai S, Zhang T, Ito Y. Preparative isolation and purification of rupestonic acid from the Chinese medicinal plant Artemisia rupestris L. by high-speed counter-current chromatography. J Chromatogr A. 2005;1076:198-201 pubmed
    ..From 200 mg of the crude extract, 27.9 mg of rupestonic acid was obtained at over 98% purity as determined by HPLC analysis, and its chemical structure was confirmed by MS, 1H and 13C nuclear magnetic resonance. ..
  6. Dravid P, Bhamidipati R, Mullangi R, Srinivas N. Validation of a simple bioanalytical method for the determination of DRF-6196, a novel oxazolidinone, in mouse plasma: application to a single-dose pharmacokinetic study. Arzneimittelforschung. 2005;55:239-44 pubmed
    ..benchtop, autosampler and freeze/thaw cycles. The stability of DRF-6196 was established for 1 month at -80 degrees C. The assay method was successfully applied to a pharmacokinetic study of DRF-6196 in mice. ..
  7. Piacenza M, Grimme S. Van der Waals complexes of polar aromatic molecules: unexpected structures for dimers of azulene. J Am Chem Soc. 2005;127:14841-8 pubmed
    ..General rules for predicting stable van der Waals complexes of polar pi systems are discussed. ..
  8. Tolouee M, Alinezhad S, Saberi R, Eslamifar A, Zad S, Jaimand K, et al. Effect of Matricaria chamomilla L. flower essential oil on the growth and ultrastructure of Aspergillus niger van Tieghem. Int J Food Microbiol. 2010;139:127-33 pubmed publisher
    ..These findings indicate the potential of M. chamomilla L. essential oil in preventing fungal contamination and subsequent deterioration of stored food and other susceptible materials. ..
  9. Blay G, García B, Molina E, Pedro J. Syntheses of (+)-alismoxide and (+)-4-epi-alismoxide. J Org Chem. 2006;71:7866-9 pubmed
    ..6 value indicates that significant amounts of alismoxide result from biosynthetic processes. Furthermore, the structure of the natural guaienediol isolated from Silphium perfoliatum has been corrected to (-)-alismoxide. ..
  10. Kabouchi B, Assongo C, Benali B. [Study of the electronic transitions of azulene and several of it's derivitives and their auto-association by the monopole-dipole atomic interaction (AMDI) model]. Spectrochim Acta A Mol Biomol Spectrosc. 2000;56A:1739-44 pubmed
    ..These spectra are obtained for the first time using the atom monopole dipole interaction model and compared to those given experimentally by other authors. ..
  11. Li F, Song Q, Yang L, Wu G, Zhang X. Supra-amphiphiles formed by complexation of azulene-based amphiphiles and pyrene in aqueous solution: from cylindrical micelles to disklike nanosheets. Chem Commun (Camb). 2013;49:1808-10 pubmed publisher
  12. Shi X, Ying X, Deng Z. Dye sublimation as a measure of accumulated heat exposure. Chemphyschem. 2013;14:3467-71 pubmed publisher
    ..Mass transfer from the sublimation layer to the adsorption layer strongly depends on temperature and results in a gradual color change in the adsorption layer. The total color change reflects the accumulated heat exposure. ..
  13. Saitoh M, Sugiyama A, Nakazawa T, Hashimoto K. Cardiovascular effects of orally administered HNS-32, an originally synthesized azulene-1-carboxamidine derivative, assessed in the in vivo rat model. Jpn J Pharmacol. 2002;89:316-9 pubmed
    ..These results suggest that HNS-32 is an orally active slowly-acting calcium plus sodium channel blocker. ..
  14. Pham W, Weissleder R, Tung C. An azulene dimer as a near-infrared quencher. Angew Chem Int Ed Engl. 2002;41:3659-62, 3519 pubmed
  15. Bhamidipati R, Venkatesh P, Dravid P, Narasimhulu P, Tvrs S, Das J, et al. Assessment of oral bioavailability and preclinical pharmacokinetics of DRF-6196, a novel oxazolidinone analogue, in comparison to linezolid. Eur J Drug Metab Pharmacokinet. 2005;30:187-93 pubmed
    ..Although plasma levels of DRF-6196 were lesser compared to linezolid in the initial hours, it may not have any consequences on the clinical effectiveness of the molecule. ..
  16. Fiori J, Gotti R, Valgimigli L, Cavrini V. Guaiazulene in health care products: determination by GC-MS and HPLC-DAD and photostability test. J Pharm Biomed Anal. 2008;47:710-5 pubmed publisher
    ..Moreover, the described methods can offer a useful analytical support for photostability studies of GA, a photolabile natural compound, in creams. ..
  17. Ueki J, Sakagami H, Wakabayashi H. Anti-UV activity of newly-synthesized water-soluble azulenes. In Vivo. 2013;27:119-26 pubmed
    ..These data suggest the possible applicability of newly-synthesized water-soluble azulenes as skin care products protecting from UV irradiation.
  18. De Waele V, Schmidhammer U, Mrozek T, Daub J, Riedle E. Ultrafast bidirectional dihydroazulene/vinylheptafulvene (DHA/VHF) molecular switches: photochemical ring closure of vinylheptafulvene proven by a two-pulse experiment. J Am Chem Soc. 2002;124:2438-9 pubmed
    ..As a result, the DHA/VHF system is found to be a multifold switchable system by itself: it is both a very fast photoreversible switch and a photochemical/thermal switch with a thermal lock mode. ..
  19. Kitai J, Kobayashi T, Uchida W, Hatakeyama M, Yokojima S, Nakamura S, et al. Photochromism of a diarylethene having an azulene ring. J Org Chem. 2012;77:3270-6 pubmed publisher
    ..On the other hand, another derivative having thiophene rings did not show any photochromism. The results clearly show the importance of the coplanarity of the system for the photoisomerization. ..
  20. Bryant H, Schultz N, Thomas H, Parker K, Flower D, Lopez E, et al. Specific killing of BRCA2-deficient tumours with inhibitors of poly(ADP-ribose) polymerase. Nature. 2005;434:913-7 pubmed
    ..The use of an inhibitor of a DNA repair enzyme alone to selectively kill a tumour, in the absence of an exogenous DNA-damaging agent, represents a new concept in cancer treatment. ..
  21. Rahimi Nasrabadi M, Ahmadi F, Batooli H. Chemical composition of essential oil and in vitro antioxidant activities of the essential oil and methanol extracts of Eucalyptus loxophleba. Nat Prod Res. 2012;26:669-74 pubmed publisher
    ..1?±?1.3) was found to be stronger. In addition, the amounts of total phenol components in the polar subfraction (273.0?±?2.6?µg?mg?¹) and nonpolar subfraction (146.3?±?2.5?µg?mg?¹) were determined. ..
  22. Amagase K, Nakamura E, Endo T, Hayashi S, Hasumura M, Uneyama H, et al. New frontiers in gut nutrient sensor research: prophylactic effect of glutamine against Helicobacter pylori-induced gastric diseases in Mongolian gerbils. J Pharmacol Sci. 2010;112:25-32 pubmed
    ..pylori-induced gastric diseases in vivo. These results suggest that glutamine/marzulene would be useful for prophylactic treatment of H. pylori-induced gastric diseases in patients. ..
  23. Shao H, Nan P, Peng S, Zhang C. [Study of chemical constituents of essential oil from flowers of Mikania micrantha H.B.K]. Zhong Yao Cai. 2001;24:341-2 pubmed
    ..95%), allo-aromadendrene (11.67%), beta-caryophyllene (9.17%), 1H-inden-1-one, 5-(1, 1-dimethylethyl)-2, 3-(6.23%), beta-himaohalene (4.56%), trans-alpha-bergamotene (4.09%), limonene (3.68%), beta-ocimene (2.53%). ..
  24. Wang L, Yan J, Fu P, Parekh K, Yu H. Photomutagenicity of cosmetic ingredient chemicals azulene and guaiazulene. Mutat Res. 2003;530:19-26 pubmed
    ..Therefore, extreme care must be taken when using cosmetic products with azulene/guaiazulene as ingredients since after applying these products on the skin, exposure to sunlight is inevitable. ..
  25. Qi D, Zhang L, Jiang J. Toward panchromatic organic functional molecules: density functional theory study on the nature of the broad UV-Vis-NIR spectra of substituted tetra(azulene)porphyrins. J Mol Graph Model. 2012;38:304-13 pubmed publisher
  26. Asato A, Peng A, Hossain M, Mirzadegan T, Bertram J. Azulenic retinoids: novel nonbenzenoid aromatic retinoids with anticancer activity. J Med Chem. 1993;36:3137-47 pubmed
    ..In general, azulenic retinobenzoic acid analogs structurally akin to TTNPB were more effective than flexible side chain analogs related to retinoic acid. ..
  27. Kordali S, Cakir A, Mavi A, Kilic H, Yildirim A. Screening of chemical composition and antifungal and antioxidant activities of the essential oils from three Turkish artemisia species. J Agric Food Chem. 2005;53:1408-16 pubmed
    ..All of the studied essential oils showed antioxidant activity, but camphor and 1,8-cineole did not. ..
  28. Chib R, Shah B, Andotra S, Bharadwaj V, Gupta R, Taneja S, et al. Quantification of sesquiterpene lactones in Parthenium hyterophorous by normal-phase HPLC. J Chromatogr Sci. 2013;51:950-3 pubmed publisher
    ..999). The method was developed to study the levels of parthenin and coronopilin in the leaves and flowers of P. hysterophorous collected during different seasons, and the method was validated by analyzing the spiked samples. ..
  29. Kawamata J, Suzuki Y. A novel molecular design strategy for efficient two-photon absorption materials. Curr Pharm Biotechnol. 2012;13:2569-74 pubmed
    ..This strategy enhances ?(2) without significantly red shifting the OPA band. ..
  30. Hu H, Przhonska O, Terenziani F, Painelli A, Fishman D, Ensley T, et al. Two-photon absorption spectra of a near-infrared 2-azaazulene polymethine dye: solvation and ground-state symmetry breaking. Phys Chem Chem Phys. 2013;15:7666-78 pubmed publisher
  31. Thang T, Huong L, Dai D, Ogunwande I. A comparative analysis of essential oils of Goniothalamus macrocalyx Ban., Goniothalamus albiflorus Ban. and Goniothalamus tamirensis Pierre ex Fin. & Gagnep. from Vietnam. Nat Prod Res. 2013;27:1999-2005 pubmed publisher
    ..tamirensis was characterised by abundance of ?-pinene (33.4%), viridiflorol (18.5%) and ?-caryophyllene (12.4%), whereas ?-gurjunene (11.2%), ?-caryophyllene (10.9%) and ?-cadinene (10.3%) predominates in the stem oil. ..
  32. Hasegawa T, Yoshitome K, Fujihara T, Santoso M, Aziz M. Characteristic Changes in the Aroma Profile of Patchouli Depending on Manufacturing Process. J Oleo Sci. 2017;66:863-869 pubmed publisher
    ..Comparing the odors and constituents demonstrated that the aroma profile of patchouli depends on the manufacturing process. ..
  33. Satoh Y, Hatori C, Ito H. Novel potent antagonists of human neuropeptide Y-Y5 receptor. Part 4: tetrahydrodiazabenzazulene derivatives. Bioorg Med Chem Lett. 2002;12:1009-11 pubmed
    ..The structure-activity relationships are described. Compounds 7 (FR240662) and 16 (FR252384) were especially attractive owing to their high affinities for the NPY-Y5 receptors, oral absorption and permeability to brain. ..
  34. Michalak K, Wicha J. Total synthesis of a CD-ring: side-chain building block for preparing 17-epi-calcitriol derivatives from the Hajos-Parrish dione. J Org Chem. 2011;76:6906-11 pubmed publisher
    ..An efficient synthesis of the key building block for 17-epi-calctriol from the Hajos-Parrish dione involving a sequence of diastereoselective transformation of the azulene core and the side-chain construction is presented. ..
  35. Devillers I, Pevet I, Jacobelli H, Durand C, Fasquelle V, Puaud J, et al. New substituted triaza-benzo[cd]azulen-9-ones as promising phosphodiesterase-4 inhibitors. Bioorg Med Chem Lett. 2004;14:3303-6 pubmed
  36. Ali M, Telfer B, McCrudden C, O Rourke M, Thomas H, Kamjoo M, et al. Vasoactivity of AG014699, a clinically active small molecule inhibitor of poly(ADP-ribose) polymerase: a contributory factor to chemopotentiation in vivo?. Clin Cancer Res. 2009;15:6106-12 pubmed publisher
    ..Vasoactive concentrations of AG014699 do not cause detrimental side effects to gut motility and may increase the range of therapeutics with which AG014699 could be combined with for clinical benefit. ..
  37. Silva Garcez A, Nunez S, Lage Marques J, Jorge A, Ribeiro M. Efficiency of NaOCl and laser-assisted photosensitization on the reduction of Enterococcus faecalis in vitro. Oral Surg Oral Med Oral Pathol Oral Radiol Endod. 2006;102:e93-8 pubmed
    ..2%, a significantly higher bacterial reduction than NaOCl. Laser photosensitization was effective for reducing E. faecalis in root canals and could be an adjunct to endodontic treatment. ..
  38. Nakamichi K, Nakano T, Yasuura H, Izumi S, Kawashima Y. Stabilization of sodium guaiazulene sulfonate in granules for tableting prepared using a twin-screw extruder. Eur J Pharm Biopharm. 2003;56:347-54 pubmed
    ..Furthermore, a twin-screw extruder with kneading paddle elements is useful for uniformly dispersing water to prepare stable formulations of GAS-Na. ..
  39. Pathem B, Zheng Y, Morton S, Petersen M, Zhao Y, Chung C, et al. Photoreaction of matrix-isolated dihydroazulene-functionalized molecules on Au{111}. Nano Lett. 2013;13:337-43 pubmed publisher
    ..An order of magnitude decrease in the photoreaction cross section of surface-bound dihydroazulenes was observed when compared with the cross sections of these molecules in solution. ..
  40. Abou Zied O. A spectroscopic study of the inclusion of azulene by beta- and gamma-cyclodextrins. Spectrochim Acta A Mol Biomol Spectrosc. 2005;62:245-51 pubmed
    ..From the induced-circular dichroism spectra, the inclusion of AZ was found to be axial in AZ:beta-CD and nearly axial in AZ:(gamma-CD)(2). ..
  41. Zhang L, Yang F, Shi W, Zhang P, Li Y, Yin S. Synthesis and antigastric ulcer activity of novel 5-isoproyl-3,8-dimethylazulene derivatives. Bioorg Med Chem Lett. 2011;21:5722-5 pubmed publisher
    ..The structure-activity relationship (SAR) shows that the lipophilic flat structure contributes to quite potent antigastric ulcer activity. ..
  42. Hashiba K, Yokoyama K, Wakabayashi H, Hashimoto K, Satoh K, Kurihara T, et al. Inhibition of LPS-stimulated NO production in mouse macrophage-like cells by azulenes. Anticancer Res. 2004;24:3939-44 pubmed
    We investigated the effect of twenty-seven azulenes on nitric oxide (NO) production by mouse macrophage-like Raw 264.7 cells. No azulene derivative alone induced NO production by the Raw 264...
  43. Bryant H, Helleday T. Poly(ADP-ribose) polymerase inhibitors as potential chemotherapeutic agents. Biochem Soc Trans. 2004;32:959-61 pubmed
    ..This review discusses the advances made in PARP inhibitor design and the mechanism by which they enhance anti-tumour therapies. ..
  44. Datta B, Rashid M, Kundu J, Rouf A, Sarker S, Datta S. Isolation and structure elucidation of viscoazucine, a novel sesquiterpene from Polygonum viscosum. Pharmazie. 2001;56:578-9 pubmed
    ..The structures of these compounds were elucidated by spectroscopic analyses, notably UV, MS and NMR...
  45. Kurihara T, Noguchi M, Noguchi T, Wakabayashi H, Motohashi N, Sakagami H. Relationship between electronic structure and cytotoxic activity of azulenes. In Vivo. 2006;20:385-9 pubmed
    ..In order to clearly divide the azulenes into three groups according to their functional groups, the CC50, four different dipole moments (muG, muESP-G, ..
  46. Guella G, Skropeta D, Mancini I, Pietra F. Calenzanane sesquiterpenes from the red seaweed Laurencia microcladia from the Bay of Calenzana, Elba Island: acid-catalyzed stereospecific conversion of calenzanol into indene- and guaiazulene-type sesquiterpenes. Chemistry. 2003;9:5770-7 pubmed
    ..A unifying mechanistic view of these branching and cascade transformations may have both heuristic value, suggesting possible artefact origin of azulenoids, and synthetic applications. ..
  47. Zhang H, Joseph J, Gurney M, Becker D, Kalyanaraman B. Bicarbonate enhances peroxidase activity of Cu,Zn-superoxide dismutase. Role of carbonate anion radical and scavenging of carbonate anion radical by metalloporphyrin antioxidant enzyme mimetics. J Biol Chem. 2002;277:1013-20 pubmed
    ..Implications of this reaction as a plausible protective mechanism in inflammatory cellular damage induced by peroxynitrite are discussed. ..
  48. Imming P, Goeters S, Pawlitzki G, Hempel B. Absolute stereochemistry of guaianolides, of matricin and its epimers, of yarrow proazulenes, and of chamazulene carboxylic acid. Chirality. 2001;13:337-41 pubmed
  49. Peet J, Selyutina A, Bredihhin A. Antiretroviral (HIV-1) activity of azulene derivatives. Bioorg Med Chem. 2016;24:1653-7 pubmed publisher
    ..A series of eighteen diversely substituted azulenes was synthesized and tested in vitro using HIV-1 based virus-like particles (VLPs) and infectious HIV-1 virus in ..
  50. Wang M, Zhai Y, Liang C. Two new guaiane-type sesquiterpenoids from Valeriana hardwickii and their cytotoxicity. J Asian Nat Prod Res. 2017;19:987-992 pubmed publisher
    ..Compounds 1 and 2 showed weak cytotoxicity against the lung adenocarcinoma (A549) and hepatoma (Bel7402) cell lines with IC50 values of 9.2 and 8.5 ?M, respectively. ..
  51. Smith L, Willmore E, Austin C, Curtin N. The novel poly(ADP-Ribose) polymerase inhibitor, AG14361, sensitizes cells to topoisomerase I poisons by increasing the persistence of DNA strand breaks. Clin Cancer Res. 2005;11:8449-57 pubmed
    ..Therefore, the most likely mechanism for the potentiation of topo I poison-mediated cytotoxicity by AG14361 is via PARP-1-dependent base excision repair. ..
  52. Gao P, Cook S. A reductive-Heck approach to the hydroazulene ring system: a formal synthesis of the englerins. Org Lett. 2012;14:3340-3 pubmed publisher
    ..When combined with a transannular epoxide rearrangement cascade, the reductive-Heck reaction allows rapid entry to the oxo-bridged guaiane core of the englerins. ..
  53. Pratsinis H, Haroutounian S. Synthesis and antioxidant activity of 3-substituted guaiazulene derivatives. Nat Prod Lett. 2002;16:201-5 pubmed
    ..3-Vinylguaiazulene was the most potent, possessing antioxidant activity superior than alpha-tocopherol. These derivatives were also moderate inhibitors of the proliferation of human promyelocytic leukemia cells. ..