72301-79-2 Usage
Description
2-Amino-6-[(E)-α-hydroxyiminobenzyl]-1-(isopropylsulfonyl)-1H-benzimidazole is a complex organic compound with a unique molecular structure. It is characterized by its benzimidazole core, which is substituted with an amino group at the 2nd position and a hydroxyiminobenzyl group at the 6th position. Additionally, it features an isopropylsulfonyl group attached to the 1st position. 2-Amino-6-[(E)-α-hydroxyiminobenzyl]-1-(isopropylsulfonyl)-1H-benzimidazole holds potential for various applications due to its distinct chemical properties and interactions with other molecules.
Uses
Used in Pharmaceutical Industry:
2-Amino-6-[(E)-α-hydroxyiminobenzyl]-1-(isopropylsulfonyl)-1H-benzimidazole is used as a pharmaceutical compound for its potential therapeutic effects. 2-Amino-6-[(E)-α-hydroxyiminobenzyl]-1-(isopropylsulfonyl)-1H-benzimidazole's unique structure allows it to interact with specific biological targets, making it a candidate for the development of new drugs. Its application reason lies in its ability to modulate biological pathways and potentially treat various diseases.
Used in Chemical Research:
In the field of chemical research, 2-Amino-6-[(E)-α-hydroxyiminobenzyl]-1-(isopropylsulfonyl)-1H-benzimidazole serves as a valuable compound for studying the properties and reactivity of benzimidazole derivatives. Its use in this context is driven by the need to understand the compound's potential applications in material science, medicinal chemistry, and the development of novel chemical processes.
Used in Drug Delivery Systems:
Similar to gallotannin, 2-Amino-6-[(E)-α-hydroxyiminobenzyl]-1-(isopropylsulfonyl)-1H-benzimidazole could be employed in drug delivery systems to enhance its bioavailability and therapeutic outcomes. By incorporating the compound into various carriers such as organic and metallic nanoparticles, its delivery, efficacy, and overall performance in targeted applications can be improved.
Originator
Enviroxime,Eli Lilly
Manufacturing Process
300 g (1.52 mole) of 4-aminobenzophenone were added in portions to a
stirred solution of 250 ml of acetic anhydride in 250 ml of benzene. Thetemperature of the mixture rose to about 70°C. The reaction mixture was
stirred overnight. The product was filtered, washed with benzene and dried.
The yield of 4-acetamidobenzophenone was 333.8 g (91.5 % yield), melting
point 150-152°C (Lit. melting point 155°C).23 g (0.1 mole) of 4-acetamidobenzophenone, 50 ml of acetic anhydride and
20 ml of acetic acid were stirred together. A solution of 90 % (15 ml), 10 ml
of acetic acid and 0.2 g of urea was added dropwise to the mixture. The
reaction mixture was maintained at a temperature of about 50°C. The mixture
was stirred at ambient temperature whereupon the mixture became very
thick. The thick slurry was poured over ice and the insoluble product was
filtered to yield 17.7 g (62.5 % yield) of 4-acetamido-3-nitrobenzophenone.10 g of 4-acetamido-3-nitrobenzophenone were added portion-wise to 40 ml
of sulfuric acid. The reaction temperature was moderated with a water bath.
After stirring about 45 min the reaction mixture was carefully poured over ice.
The precipitated product was filtered to yield 4-amino-3-nitrobenzophenone.50 g of 4-amino-3-nitrobenzophenone were hydrogenated at room
temperature in 945 ml of tetrahydrofuran with 15 g of Raney nickel. After 4
hours 3 equivalents of hydrogen were absorbed. The catalyst was filtered and
the filtrate was evaporated in vacuo to a solid residue. The residue was
chromatographed over silica gel using ethyl acetate as eluent. Fractions 5-9
were combined to yield 43.6 g (100 % yield) of 3,4-diaminobenzopheone.42.4 g (o.2 mole) of 3,4-diaminobenzophenone were dissolved in 100 ml of
methanol and mixed into one liter of water. 21.8 g (0.2 mole) of cyanogen
bromide were added in portions to the reaction mixture with stirring The
reaction was continued overnight. The reaction mixture was filtered and the
filtrate was neutralized (pH 7.0) with concentrated ammonium hydroxide. The
precipitated product was collected, washed with water, and dried in a vacuum
to yield 31 g (68.5%) of 2-amino-5(6)-benzoylbenzimidazole.4.5 g (20 mmole) of 2-amino-5(6)-benzoylbenzimidazole were dissolved in 30
ml of acetone and 4.0 g of triethylamine. A solution of 2.9 g (20 mmole) of
dimethylsulfamoyl chloride in 10 ml of acetone was added dropwise to the
reaction mixture. The mixture was heated at reflux overnight. The reaction
mixture was poured into 400 ml of water. The product was extracted with
chloroform. The extract was washed with water, dried (Na2SO4) and
evaporated in vacuo. The residue was crystallized from ethyl acetate to yield
1.06 g of 1-dimethylaminosulfonyl-2-amino-6-benzoylbenzimidazole, melting
point 206-208°C.172 mg of 1-dimethylaminosulfonyl-2-amino-5(6)-benzoylbenzimidazole, 100
mg of hydroxylamine hydrochloride and 20 ml of methanol were refluxed for
16 hours. The reaction mixture was concentrated to one-half the original
volume by heating on the steam bath. 10 ml of buffer (pH=7.0) were added
to the mixture. The product precipitated and was filtered to yield 116 mg of 1-
dimethylaminosulfonyl-2-amino-5(6)-(α-hydroxyiminobenzyl)benzimidazole,
melting point 180-183°C.
Therapeutic Function
Antiviral
Check Digit Verification of cas no
The CAS Registry Mumber 72301-79-2 includes 8 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 5 digits, 7,2,3,0 and 1 respectively; the second part has 2 digits, 7 and 9 respectively.
Calculate Digit Verification of CAS Registry Number 72301-79:
(7*7)+(6*2)+(5*3)+(4*0)+(3*1)+(2*7)+(1*9)=102
102 % 10 = 2
So 72301-79-2 is a valid CAS Registry Number.
InChI:InChI=1/C17H18N4O3S/c1-11(2)25(23,24)21-15-10-13(8-9-14(15)19-17(21)18)16(20-22)12-6-4-3-5-7-12/h3-11,22H,1-2H3,(H2,18,19)/b20-16+
72301-79-2Relevant articles and documents
Synthesis of Syn and Anti Isomers 6-methyl>-1--1H-benzimidazol-2-amine. Inhibitors of Rhinovirus Multiplication
Wikel, J. H.,Paget, C. J.,DeLong, D. C.,Nelson, J. D.,Wu, C. Y. E.,et al.
, p. 368 - 372 (2007/10/02)
The synthesis and antirhinovirus activity of syn and anti isomers of 6-methyl>-1--1H-benzimidazol-2-amine (4 and 5) are reported.The structural assignements of 4 and 5 are based upon 13C NMR spectra of both isomers and also X-ray analysis of 5.The anti-isomer 5 was more potent than the syn-isomer 4 when compared as an inhibitor of rhinovirus multiplication in vitro.Both isomers inhibited multiplication of 15 differrent serotypes of rhinovirus.
