70042-27-2 Usage
Description
1-(2,3,4-tri-O-acetylpentopyranosyl)-1H-imidazole-4,5-dicarbonitrile is a complex chemical compound that features a pentopyranosyl group attached to an imidazole ring, along with two carbonitrile groups. 1-(2,3,4-tri-O-acetylpentopyranosyl)-1H-imidazole-4,5-dicarbonitrile is characterized by the presence of acetyl groups in the pentopyranosyl group, which protect the hydroxyl groups and contribute to the compound's stability. The imidazole ring, a five-membered structure with two nitrogen atoms, and the carbonitrile groups endow the compound with high reactivity. This unique structure and reactivity suggest potential applications in medicinal chemistry, biochemistry, and organic synthesis, although further research is necessary to determine its specific properties and uses.
Uses
1. Used in Medicinal Chemistry:
1-(2,3,4-tri-O-acetylpentopyranosyl)-1H-imidazole-4,5-dicarbonitrile is used as a building block for the synthesis of novel pharmaceutical compounds due to its unique structure and reactivity. Its potential applications in this field may include the development of new drugs targeting various diseases.
2. Used in Biochemistry:
In the field of biochemistry, 1-(2,3,4-tri-O-acetylpentopyranosyl)-1H-imidazole-4,5-dicarbonitrile may be utilized as a component in the study of biological processes and interactions. Its reactivity and structural features could make it a valuable tool for understanding complex biochemical mechanisms.
3. Used in Organic Synthesis:
1-(2,3,4-tri-O-acetylpentopyranosyl)-1H-imidazole-4,5-dicarbonitrile is used as an intermediate in the synthesis of various organic compounds. Its high reactivity and unique structure make it a promising candidate for the development of new synthetic pathways and the creation of novel organic molecules with potential applications in various industries.
4. Used in Drug Delivery Systems:
Similar to gallotannin, 1-(2,3,4-tri-O-acetylpentopyranosyl)-1H-imidazole-4,5-dicarbonitrile could be employed in the development of drug delivery systems. Its unique structure and reactivity may allow for the design of innovative carriers and vehicles for drug molecules, potentially improving their delivery, bioavailability, and therapeutic outcomes.
5. Used in Anticancer Applications:
Although not explicitly mentioned in the provided materials, the compound's potential reactivity and structural features may also make it a candidate for use in anticancer applications. Further research would be required to explore its efficacy and mechanisms of action in this context.
Check Digit Verification of cas no
The CAS Registry Mumber 70042-27-2 includes 8 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 5 digits, 7,0,0,4 and 2 respectively; the second part has 2 digits, 2 and 7 respectively.
Calculate Digit Verification of CAS Registry Number 70042-27:
(7*7)+(6*0)+(5*0)+(4*4)+(3*2)+(2*2)+(1*7)=82
82 % 10 = 2
So 70042-27-2 is a valid CAS Registry Number.
70042-27-2Relevant articles and documents
Nucleosides from Carbohydrate Adducts of Diaminomaleonitrile. A Novel Synthesis of 5-Amino-1-(β-D-ribofuranosyl)imidazole-4-carboxamide and 5-Amino-1-(β-D-ribopyranosyl)imidazole-4-carboxamide
Ferris, James P.,Devadas, Balekadru,Huang, Chun-Hsien,Ren, Wu-Yen
, p. 747 - 754 (2007/10/02)
The stereospecific and regiospecific synthesis of 5-amino-1-(β-D-ribofuranosyl)imidazole-4-carboxamide (16) was achieved in six steps.A key intermediate in the synthesis, N-(2',3',5'-tri-O-benzoyl-β-D-ribofuranosyl)diaminomaleonitrile (3), was prepared by two routes: the reaction of diaminomaleonitrile (1) with 1-bromo-2,3,5-tri-O-benzoyl-β-D-ribofuranose (2) and the reaction of the bis(trimethylsilyl) derivative of diaminomaleonitrile (4) with 1-O-acetyl-2,3,5-tri-O-benzoyl-β-D-ribofuranose (5).Reaction of 3 triethyl orthoformate yielded 4,5-dicyano-1-(2',3',5'-tri-O-benzoyl-β-D-ribofuranosyl)imidazole (10).Alternatively 10 was synthesized by the acid-catalyzed cyclization of the N-formyl derivative 12 which was prepared by the reaction of the trimethylsilyl derivative of N-formyldiaminomaleonitrile 11 with 5.Deblocking 10 with 1 equiv of sodium methoxide at room temperature resulted in the regiospecific formation of the 5-imidate 14.Reaction of 14 with alkaline hypochlorite yielded 5-amino-1-(β-D-ribofuranosyl)imidazole-4-carbonitrile (15) by a Hofmann rearrangement.Alkaline hydrolysis of the nitrile function yielded the corresponding amide 16. 5-Amino-1-(β-D-ribopyranosyl)imidazole-4-carboxamide (28) was prepared by a similar synthetic sequence.Reaction of diaminomaleonitrile (1) with ribose gave a mixture of the α- and β-anomers of D-ribopyranosyldiaminomaleonitrile (17).Compound 17 was converted to a mixture of the anomeric tri-O-acetates which on heating with triethyl orthoformate gave a separable mixture of the α- and β-anomers of 4,5-dicyano-1-(2',3',4'-tri-O-acetyl-D-ribopyranosyl)imidazole (19 and 20, respectively).Reaction of 19 with NH3/CH3OH at room temperature cleaved the three acetyl groups and regiospecifically converted the 5-cyano to the 5-imidate (26).The regiospecificity is due to the attack of the 2'-oxy anion on the 5-cyano group as shown by the isolation of the cyclic imidate 25 when the reaction is carried out at 0 deg C.The Hofmann rearrangement of imidate 26 followed by alkaline hydrolysis gave 5-amino-1-(β-D-ribopyranosyl)imidazole-4-carbonitrile 27 and 28, respectively.The 1H and 13C NMR spectra of imidates 14 and 26 have multiple peaks for the protons and carbons, respectively.Restricted rotation of the 5-imidate (energy of activation 18 kcal) results in isomers of 14 and 26 with different NMR spectra.The C-2, H-1' coupling constants of 2.5-3.1 Hz of the isomeric species comprising imidates 14 and 26 are consistent with a H-2, H-1' dihedral angle of 135 deg and an anti orientation of the imidazole with respect to the ribose ring; a conclusion confirmed by NOE measurements.
