New Syntheses of the Bis-Guanylhydrazone and Bis-Thiosemicarbazone of Methylglyoxal

Keiko, N. A.; Mamashvili, T. N.

doi:10.1007/s11094-005-0088-x

Cited by 3 publications

(3 citation statements)

References 17 publications

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“…Another modification involves the use of molecular sieves to induce reaction between an aldehyde or ketone with a thiosemicarbazide in DMF [50]. In some cases to make thiosemicarbazide completely soluble, 1-2 ml of concentrated HCl [51,52] or acetic acid is added [53] to ensure the complete condensation. Table 1 gives a list of metals whose complexes with thiosemicarbazones have been reported.…”

Section: Synthesis Of Ligandsmentioning

confidence: 99%

Bonding and structure trends of thiosemicarbazone derivatives of metals—An overview

Lobana¹,

Sharma²,

Bawa³

et al. 2009

Coordination Chemistry Reviews

610

332

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Section: Synthesis Of Ligandsmentioning

confidence: 99%

Bonding and structure trends of thiosemicarbazone derivatives of metals—An overview

Lobana¹,

Sharma²,

Bawa³

et al. 2009

Coordination Chemistry Reviews

610

332

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“…Guanidinium ions are known to be a biologically active structural motif present in a number of pharmacophores . They are also a part of many important building blocks in cells, such as the amino acid arginine and the purine base guanine present in the nucleic acid.…”

Section: Introductionmentioning

confidence: 99%

Neighboring Effect in Fragmentation Pathways of Cage Guanylhydrazones in the Gas Phase

2013

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ESI-MS/MS investigation of the mono- and bis(guanylhydrazone) derivatives 1-5 based on adamantane and pentacycloundecane (PCU) skeleton was described. Elimination of neutral guanidine is the most abundant reaction channel in the case of 2,4-adamantyl and PCU derivatives 4 and 5, while the elimination of CH2N2 fragment is preferred for other compounds. This was attributed to the cage opening of adamantane or PCU skeletons in the former case leading to the formation of the cyclohexyl- or cyclopropylcarbinyl carbocation stabilized by the conjugation with the guanylhydrazone subunit. The main fragmentation pathways observed experimentally were analyzed by using DFT calculations. All investigated bis(guanylhydrazone)s formed dications and their abundances were found to be proportional to the interguanidine distance in the considered ions. Calculation of the first and the second proton affinities supported qualitative interpretation of the dication abundance. Close contact of two guanidine subunits is thus confirmed to be crucial in determining preferential fragmentation pathway and to suppress formation of the dication.

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“…In addition, some derivatives of α-alkoxysubstituted α,β-unsaturated aldehydes are known to possess DNA-inhibiting and antitumor activity [ 15 ]. α-Alkoxysubstituted α,β-unsaturated aldehydes are the chemical equivalents of methylglyoxal [ 16 ], a low molecular regulator of cell growth in animals, plants, and microbes [ 17 , 18 ]. Derivatives of α-alkoxycinnamic aldehydes are met in plants and are structural fragments of lignin [ 4 ].…”

Section: Synthesis Of α-Functionally Substituted αβ-Unsaturated Aldehydesmentioning

confidence: 99%

α-Functionally Substituted α,β-Unsaturated Aldehydes as Fine Chemicals Reagents: Synthesis and Application

2021

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α-Functionalized α,β-unsaturated aldehydes is an important class of compounds, which are widely used in fine organic synthesis, biology, medicine and pharmacology, chemical industry, and agriculture. Some of the 2-substituted 2-alkenals are found to be the key metabolites in plant and animal cells. Therefore, the development of efficient methods for their synthesis attracts the attention of organic chemists. This review focusses on the recent advances in the synthesis of 2-functionally substituted 2-alkenals. The approaches to the preparation of α-alkyl α,β-unsaturated aldehydes are not included in this review.

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New Syntheses of the Bis-Guanylhydrazone and Bis-Thiosemicarbazone of Methylglyoxal

Abstract: New methods of synthesis of methylglyoxal bis-guanylhydrazone (as bis-hydrochloride) and methylglyoxal bis-thiosemicarbazone are developed, which are based on the reactions of 2-ethoxypropenal with aminoguanidine and thiosemicarbazide in an acid medium.

Cited by 3 publications

References 17 publications

Bonding and structure trends of thiosemicarbazone derivatives of metals—An overview

Bonding and structure trends of thiosemicarbazone derivatives of metals—An overview

Neighboring Effect in Fragmentation Pathways of Cage Guanylhydrazones in the Gas Phase

α-Functionally Substituted α,β-Unsaturated Aldehydes as Fine Chemicals Reagents: Synthesis and Application

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