1,3,3-Trinitroazetidine (TNAZ), a melt-cast explosive: synthesis, characterization and thermal behaviour

Sikder, Nirmala; Sikder, A. K.; Bulakh, N. R.; Gandhe, B.R.

doi:10.1016/j.jhazmat.2004.06.002

Cited by 59 publications

(24 citation statements)

References 13 publications

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“…This compound contains a unique high energetic organic nitro functional group, a gem dinitroazetidine that has not been used to date for medical and Cancer Researchpharmaceutical applications. In an aerospace setting, compounds containing this energetic functionality, such as trinitroazetidine, are designed to fragment explosively (14,24). Modification of this structure resulted in ABDNAZ, a nonexplosive, selectively activated compound with the potential for use in the treatment of cancer (15).…”

Section: Discussionmentioning

confidence: 99%

Dinitroazetidines Are a Novel Class of Anticancer Agents and Hypoxia-Activated Radiation Sensitizers Developed from Highly Energetic Materials

et al. 2012

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In an effort to develop cancer therapies that maximize cytotoxicity, while minimizing unwanted side effects, we studied a series of novel compounds based on the highly energetic heterocyclic scaffold, dinitroazetidine. In this study, we report the preclinical validation of 1-bromoacetyl-3,3-dinitroazetidine (ABDNAZ), a representative lead compound currently in a phase I clinical trial in patients with cancer. In tumor cell culture, ABDNAZ generated reactive free radicals in a concentration-and time-dependent manner, modulating intracellular redox status and triggering apoptosis. When administered to mice as a single agent, ABDNAZ exhibited greater cytotoxicity than cisplatin or tirapazamine under hypoxic conditions. However, compared with cisplatin, ABDNAZ was better tolerated at submaximal doses, yielding significant tumor growth inhibition in the absence of systemic toxicity. Similarly, when combined with radiation, ABDNAZ accentuated antitumor efficacy along with the therapeutic index. Toxicity studies indicated that ABDNAZ was not myelosuppressive and no dose-limiting toxicity was apparent following daily administration for 14 days. Taken together, our findings offer preclinical proof-ofconcept for ABDNAZ as a promising new anticancer agent with a favorable toxicity profile, either as a chemotherapeutic agent or a radiosensitizer. Cancer Res; 72(10); 2600-8. Ó2012 AACR.

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Section: Discussionmentioning

confidence: 99%

Dinitroazetidines Are a Novel Class of Anticancer Agents and Hypoxia-Activated Radiation Sensitizers Developed from Highly Energetic Materials

et al. 2012

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“…This compound contains a unique high energetic organic nitro functional group, a gem dinitroazetidine that has not been used to date for medical and pharmaceutical applications. In an aerospace setting, compounds containing this energetic functionality, such as 1,3,3 trinitroazetidine, are designed to fragment explosively to propel rockets [263]. Modification of this structure by removing one of the nitro groups and substituting it with a bromoacetate group resulted in RRx-001, a nonexplosive that may be used to treat cancer [25, 264].…”

Section: Modulation Of No Levels As a Strategy To Treat Cancermentioning

confidence: 99%

The dichotomous role of H2S in cancer cell biology? Déjà vu all over again

Kashfi

2018

Biochemical Pharmacology

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Nitric oxide (NO) a gaseous free radical is one of the ten smallest molecules found in nature, while hydrogen sulfide (HS) is a gas that bears the pungent smell of rotten eggs. Both are toxic yet they are gasotransmitters of physiological relevance. There appears to be an uncanny resemblance between the general actions of these two gasotransmitters in health and disease. The role of NO and HS in cancer has been quite perplexing, as both tumor promotion and inflammatory activities as well as anti-tumor and antiinflammatory properties have been described. These paradoxes have been explained for both gasotransmitters in terms of each having a dual or biphasic effect that is dependent on the local flux of each gas. In this review/commentary, I have discussed the major roles of NO and HS in carcinogenesis, evaluating their dual nature, focusing on the enzymes that contribute to this paradox and evaluate the pros and cons of inhibiting or inducing each of these enzymes.

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“…Using silver salts 1 and 3, metathesis reactions with aminoguanidinium chloride, diaminoguanidinium iodide, or triaminoguanidinium chloride gave the corresponding nitrogen-rich salts (aminoguanidinium cyanotetrazolate-2-oxide (5), diaminoguanidinium cyanotetrazolate-2-oxide (6), triaminoguanidinium cyanotetrazolate-2-oxide (7), aminoguanidinium cyanotetrazolate-1-oxide (8), and triaminoguanidinium cyanotetrazolate-1-oxide (9)) of the cyanotetrazolate-1 and -2 oxides after filtering off the corresponding silver halide as by-product. Crystals were grown by the slow diffusion of ether into a methanolic solution of the salt.…”

Section: Synthesismentioning

confidence: 99%

A Study of Cyanotetrazole Oxides and Derivatives thereof

Boneberg

Kirchner

Klapötke

et al. 2012

Chemistry An Asian Journal

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In this work we report on the syntheses of energetic salts of cyanotetrazolate-1- and -2-oxides; this offers a unique ability to compare the effects of tetrazole 1- versus 2-oxidation. 5-Cyanotetrazolate-2-oxide can be synthesized by oxidation of the 5-cyanotetrazolate anion with Oxone, while the corresponding 1-oxide was synthesized by the rearrangement of azidoaminofurazan. Both chemical (multinuclear NMR, IR, and Raman spectroscopies, mass spectrometry, etc.) as well as explosive (impact, friction, and static sensitivities) properties are reported for these energetic salts. Calculated explosive performances using the EXPLO5 computer code are also reported. We furthermore detail the chemistry of these two anions, and their ability to form tetrazole-carboxamides, dihydrotetrazines, and tetrazines. The ability to hydrolyze cyanotetrazole oxides to their amides was demonstrated by two copper complexes. Several crystal structures of these species are presented in addition to full chemical characterization. Finally, the unique 1,4,-bis(2-N-oxidotetrazolate)-1,2,4,5-tetrazine anion was characterized as an energetic material as its ammonium salt.

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1,3,3-Trinitroazetidine (TNAZ), a melt-cast explosive: synthesis, characterization and thermal behaviour

Cited by 59 publications

References 13 publications

Dinitroazetidines Are a Novel Class of Anticancer Agents and Hypoxia-Activated Radiation Sensitizers Developed from Highly Energetic Materials

Dinitroazetidines Are a Novel Class of Anticancer Agents and Hypoxia-Activated Radiation Sensitizers Developed from Highly Energetic Materials

The dichotomous role of H2S in cancer cell biology? Déjà vu all over again

A Study of Cyanotetrazole Oxides and Derivatives thereof

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