Methylhydrazine Research Articles

Rearrangements in the formation of pyrazolines from alkyl hydrazines and unsaturated carbonyl compounds

The isomeric composition of the 2-pyrazolines obtained by the condensation of croton aldehyde and methyl vinyl ketone with C1–C4 monoalkyl hydrazines has been studied by the GLC method. It has been shown that in the reaction of croton aldehyde with isopropyl hydrazine, isobutyl hydrazine, and, to a smaller extent, with methyl hydrazine, in addition to the 1-alkyl-5-methyl-2-pyrazolines the 1, 3-isomers are formed. In other cases, only one pyrazoline, corresponding to the structure of the carbonyl compound, is formed. Eight previously-unknown dialkyl-2-pyrazolines are described.

Reaction of 4,6-dimethoxy-5-nitropyrimidine with methylhydrazine. Formation of 4-hydrazine-6-hydroxypyrimidine

Reaction of 4,6-dimethoxy-5-nitropyrimidine with methylhydrazine. Formation of 4-hydrazine-6-hydroxypyrimidine

Radiosensitization of Shigella flexneri and Escherichia coli by methyl hydrazine, indane trione and acriflavine.

SummaryThree compounds which differ widely in their chemical reactions with cellular constituents were found to sensitize Shigella flexneri Y6R, Escherichia coli B/r and E. coli BS-1 to the effects of ionizing radiation.The radiosensitivity of survivors from bacteria treated with toxic concentrations of these compounds and then washed was the same as untreated bacteria. However, bacteria treated with non-toxic concentrations of indane trione and acriflavine and then thoroughly washed were more resistant to the effects of u.v.-light.Since the bacteria were sensitized to ionizing radiation only in the presence of the free compounds, it was concluded that sensitization to ionizing radiation could be by means of an energy-transfer mechanism between the sensitizing compound and neighbouring but not bonded vital macromolecules. Alternatively sensitization may involve interaction between short-lived, radiation-induced radicals and the sensitizing compound.

Single-Strand Breaks in DNA of Ehrlich Ascites Tumor Cells Produced by Methyl Hydrazine

Methyl hydrazine (MH) is a reducing agent and electron donor previously found to radiosensitize anoxic bacterial cells. This compound has now been shown also to radiosensitize Ehrlich ascites tumor cells in vivo (dose modifying factor of 2) at concentrations non-lethal to cells or the host mouse. When MH-treated Ehrlich ascites cells are layered upon an alkaline sucrose density gradient the resulting DNA profile resembles that of cells receiving a large dose of x-radiation, i.e., a shift toward the top of the gradient, suggesting the production of a great many single-strand breaks. This effect is also observed with nucleoprotein isolated from Ehrlich ascites cells. Incubation of MH-treated cells in saline in the absence of MH allows partial rejoining of single-strand breaks. The normal strand break repair period following radiation injury may be less effective for cells in the presence of MH, possibly explaining the observed radiosensitization effect.

Rate of reaction of methyl iodide and hydrazine in aqueous solution

ADVERTISEMENT RETURN TO ISSUEPREVArticleNEXTRate of reaction of methyl iodide and hydrazine in aqueous solutionRobert A. HastyCite this: J. Phys. Chem. 1969, 73, 2, 317–321Publication Date (Print):February 1, 1969Publication History Published online1 May 2002Published inissue 1 February 1969https://doi.org/10.1021/j100722a007RIGHTS & PERMISSIONSArticle Views178Altmetric-Citations4LEARN ABOUT THESE METRICSArticle Views are the COUNTER-compliant sum of full text article downloads since November 2008 (both PDF and HTML) across all institutions and individuals. These metrics are regularly updated to reflect usage leading up to the last few days.Citations are the number of other articles citing this article, calculated by Crossref and updated daily. Find more information about Crossref citation counts.The Altmetric Attention Score is a quantitative measure of the attention that a research article has received online. Clicking on the donut icon will load a page at altmetric.com with additional details about the score and the social media presence for the given article. Find more information on the Altmetric Attention Score and how the score is calculated. Share Add toView InAdd Full Text with ReferenceAdd Description ExportRISCitationCitation and abstractCitation and referencesMore Options Share onFacebookTwitterWechatLinked InReddit PDF (531 KB) Get e-Alerts

Treatment of some chronic hemoblastoses with a derivative of Methylhydrazine (Natulan)

Notre expérience clinique sur le Natulan est encore plutôt limitée. Depuis six mois seulement il nous a été possible obtenir ce médicament et nous n'avons traité jusqu'à présent que seize malades, tous par thérapie orale.Dans le tableau suivant nous indiquons les maladies dont étaient atteints nos patients et le résultat du traitement.Quelqu'une de nos observations mérite un bref commentaire.Le premier malade que nous avons soumis au traitement était atteint de M. de Hodgkin généralisée, désormais insensible à toute thérapie connue. Le malade était en effet très près de la mort. Et bien, le Natulan eût une influence bénigne dramatique, soit pour la rapidité, soit pour l'entité de la rémission. Mais après un mois il y eût une rechute et, malgré la therapie d'entretien, le patient est mort en cachéxie. Dans ce cas nous n'avons pas observé de phénomenès toxiques sévères sauf une légère polynevrite des membres inférieurs.Il faut encore remarquer que le Natulan a été actif aussi contre des hémoblastoses différentes de la M. de Hodgkin, c'est-à-dire le myélome, la M. de Waldenström et le lymphosarcome. Mais dans ces cas les rémissions ont été relativement plus rares et moins remarquables que dans la M. de Hodgkin.

Azamorphinan and related compounds. I. A synthesis of 2-hydroxy-N-methyl-9-azamorphinan (studies on the syntheses of heterocyclic compounds. CCXIV.

In order to examine the analgesic action of azamorphinan attempt to synthesize 3-hydroxy-N-methyl-9-azamorphinan (III) which has an additional nitrogen in morphinan ring was carried out successfully. Hydrolysis of 2-ethoxycarbonylmethyl-2-(3-methoxyphenyl) cyclohexanone (IX), which was obtained by condensation of 2-(3-methoxyphenyl) cyclohexanone (VIII) with ethyl bromoacetate in the presence of sodium amide, was first examined to give 2-carboxymethyl-2-(3-methoxyphenyl) cyclohexanone (X), whose methylhydrazination with methyl hydrazine afforded 3, 4, 5, 6, 7, 8-hexahydro-2H, 4aH-4a-(3-methoxyphenyl)-2-methyl-3-oxocinnoline (XI). Secondly, reduction of the preceding compound (XI) with lithium aluminum hydride gave 4a-(3-methoxyphenyl)-2-methyldecahydrocinnoline (XII), which was converted into 3-methoxy-N-methyl-9-azamorphinan (XV) by Pictet-Spengler reaction with formalin and hydrochloric acid. Finally, demethylation of XV with hydrobromic acid afforded 3-hydroxy-9-azamorphinan (III), which was characterized as the picrate of its benzoate (XVI). Furthermore, conformation of XV was discussed.

Radiosensitization of Escherichia coli by methyl hydrazine and the effect of oxygen.

THIOL-BINDING agents such as N-ethylmaleimide1, iodoacetamide2 and hydroxymercuribenzoate3 are effective bacterial radiosensitizers, particularly with the more radioresistant bacteria2. Sensitization of bacteria by these compounds is believed to be a result of their common ability to bind sulphydryl groups within the bacterial cell which can function either as natural radioprotective agents by radical scavenging or as repair agents for DNA radicals formed by hydrogen abstraction4–6. Alternatively, enzyme repair reactions may be inhibited by the presence of these sulphydryl poisons, a view recently emphasized by Alexander, Lett and Dean7. Another group of radiosensitizing compounds are the stable free radicals such as oxygen8, nitric oxide9, di-t-butyl nitroxide10, and copper ions11. Still a third class of compounds known to radiosensitize bacteria are halogen containing substances such as chloral hydrate12 or chloroform13 which presumably act by the formation of short-lived halogen radicals toxic to the bacterial cell (the halogen containing sulphydryl poison iodoacetamide may be in this category too) or by formation of long lived toxic radiolytic product. Most of these agents are found to be more effective in nitrogen than in oxygen radiation conditions. Halogenated pyrimidines such as 5-bromouracil sensitize by yet another mechanism, because they require incorporation into cellular DNA in order to be effective.

Studies on the metabolic fate of the C14 labeled methyl group of a methylhydrazine derivative in P815 mouse leukemia.

Neben der bereits beschriebenen teilweisen Oxydation der endstandigen N-Methylgruppe von 1-Methyl-14C-2-p-(isopropylcarbamoyl)benzylhydrazin-Hydrochlorid (MBH) (NSC 77213) in vivo5 lassen die hier aufgefuhrten Resultate auch auf eine Transmethylierung dieser Methylgruppe schliessen.

Comparative metabolic studies with Natulan, methylhydrazine and methylamine in rats.

Nach intraperitonealer Verabreichung von Natulan®, Methylamin oder Methylhydrazin an Ratten konnte im Urin neben den verabreichten Stoffen Methylamin nachgewiesen werden, dagegen wurde Methylhydrazin als Metabolit von Natulan® nicht gefunden. Das Auftreten von Methylamin nach Gabe der erwahnten Hydrazinverbindungen zeigt, dass der Ratten-organismus nicht nur, wie bisher bekannt, aromatische Azoverbindungen an der N-N-Bindung spalten kann, sondern auch aliphatisch-araliphatische.

Chemical Sensitization of Mice to Radiation Lethality

SummaryThiol binding reagents such as N-ethyl maleimide, iodoacetamide, and chloromercuribenzoate are known to potentiate or sensitize the radiation inactivation of bacteria. These agents have been tested for their ability to sensitize mice when injected intraperitoneally immediately before whole-body irradiation. The results have shown that mice given a threshold lethal dose of 525 rad after injection with thiol-binding agents exhibit 30–60 per cent greater mortality than the controls. The sensitizing effect is believed not to be due to drug toxicity, and decreases with increasing dose of radiation. At the higher radiation dose of 810 rad, 50 per cent mortality occurs in 4–6 days, which suggests gastro-intestinal rather than bone-marrow damage as the cause of death. Other chemical agents known to radiosensitize bacteria have been tested in mice: thioglycolic acid and 5-bromouracil were not effective but methyl hydrazine was a potent radiosensitizer.

Demethylation in vivo of Natulan, a tumour-inhibiting methylhydrazine derivative.

Die intraperitoneale Verabreichung von 1-14CH3-Natulan bei der Maus und der Ratte hat eine Ausscheidung von14CO2 in der Atemluft zur Folge. Die Demethylierungsrate in vivo betragt bei der Maus 3,1, bei der Ratte 1,7µM/h/100 g Korpergewicht. Sie wird bei der Ratte durch Behandlung mit Phenobarbital mehr als verdoppelt. Uber das Substrat der N-Demethylierung lasst sich keine sichere Aussage machen.

Pyrazolo [3,4‐b]pyridines and pyrazolo[3′,4′:6,5]pyrido[2,3‐d]pyrimidines

Abstract3,6‐Diamino‐5‐cyanopyrazolo[3,4‐b]pyridine (III) and 1‐methyl‐3, 6‐diamino‐5‐cyanopyrazolo[3,4‐b]pyridine (IV) were formed by treatment of 2‐amino‐6‐chloro‐3, 5‐dicyanopyridine with hydrazine and methylhydrazine. Pyrazolo[3′,4′:6,5]pyrido[2,3‐d]pyrimidines were formed from IV and from a number of its derivatives.

An antineoplastic C14-labeled methylhydrazine derivative in P815 mouse leukemia. A metabolic study.

Die endstandige N-Methyl-Gruppe von 1-Methyl-C14-2-p-(isopropylcarbamoyl)benzylhydrazin-Hydrochlorid (MBH) (Ro 4-6467) erwies sich in In-vivo-Experimenten metabolisch labil, wird teilweise oxydiert und Bestandteil des Formiatpools.

EXPERIENCES WITH METHYLHYDRAZINE.

EXPERIENCES WITH METHYLHYDRAZINE.

REACTIONS OF DIETHYLBERYLLIUM AND DIETHYLBERYLLIUM TRIMETHYLAMINE WITH THE METHYLHYDRAZINES

The reactions of Et2Be and Et2Be:NMe3 with the methylhydrazines produce the following compounds: Et2Be:NMe3 and H2NNMeH give (EtBeMeNNH2)n, Et2Be and H2NNMeH give Be(MeNNH2)2, Et2Be and H2NNMe2 give Be(HNNMe2)2, Et2Be and HMeNNMeH give (EtBeMeNNMeH)n, Et2Be:NMe3 and HMeNNMe2 give approximately 50% Et2Be: HMeNNMe2 and 50% (EtBeMeNNMe2)n, Et2Be and HMeNNMe2 give primarily (EtBeMeNNMe2)n, and Et2Be and Me2NNMe2 give (Et2Be2):Me2NNMe2.

Preparation of Some Acylated Methylhydrazines.

Preparation of Some Acylated Methylhydrazines.

Recherches Dans la Série Des Benzofurannes XI‐Synthèse de pyrazoles et d'isoxazoles a partir de composés céto‐3 benzofuranniques

AbstractIt is shown that hydrazine and methyl hydrazine react with 3‐keto benzofurans to yield trisubstituted pyrazoles having a phenolic character. Several pyrazole compounds have been prepared. R. Royer and E. Bisagni have shown that phenolic trisubstituted isoxazoles are formed by the action of hydroxylamine on the 3‐keto benzofurans; we have prepared other phenolic isoxazoles, thus showing how very general the reaction is.Finally we have synthesised β‐N‐diethylaminoethylether derivatives of all phenolic pyrazoles and isoxazoles.

SOME REACTIONS OF ORGANOALUMINUM COMPOUNDS WITH NITROGEN-CONTAINING BASES

The reactions of Me3Al with Me2NNMe2 and Me2NCH2NMe2 have yielded complexes whose n.m.r. spectra suggest cyclic structures. They have the formulas Me3Al:Me2NNMe2 and Me3Al:Me2NCH2NMe2 respectively. Me3Al reacts with Me2NCH2CH2NMe2 to form a complex with a linear structure and the formula Me3Al:Me2NCH2CH2NMe2:AlMe3.The reactions of H3Al:NMe3 with several methyl hydrazines have yielded the following compounds: [—Al(HNNHMe)NHNMe—]n, [—HAlNNMe2—]n, H2Al—NHNEt2, [(—HAlNNEt2—):NMe3]n, and H2Al—NMe2. No reaction occurred between H3Al·(Et2O)n and tetramethylhydrazine and the reaction of 3 moles of H2NNMe2 with 1 mole of H3Al:NMe3 yielded a compound for which no structural formula could be assigned, but which had emperical formula C4H15N5Al.

Cytological investigations with a new class of cytotoxic agents. methylhydrazine derivatives.

Mittels cytologischer Untersuchungen wurde versucht, einen Einblick in den Wirkungsmechanismus der tumorhemmenden Methylhydrazinverbindungen zu gewinnen. 1-Methyl-2-benzyl-hydrazinphosphat bewirkt beim Ehrlich-Ascites-Carcinom der Maus einen Abfall des Mitoseindexes, eine Verschiebung des Mitosephasenindexes zugunsten der Metaphase sowie das Auftreten von Chromatidbruchen. Diese Befunde werden diskutiert.