5504-24-5

Usage

Uses

Used in Pharmaceutical Synthesis:
2-PHENYL-ACETAMIDINE is used as a synthetic intermediate for the development of non-nucleoside reverse transcriptase inhibitors (NNRTIs). These inhibitors play a crucial role in the treatment of HIV/AIDS by blocking the activity of the reverse transcriptase enzyme, which is essential for the replication of the virus.
Additionally, 2-PHENYL-ACETAMIDINE is utilized in the preparation of naltrexone-derived pyridoand pyrimidomorphinans. Naltrexone is an opioid antagonist used to treat opioid dependence and alcohol use disorder. The synthesis of novel naltrexone-derived compounds can potentially lead to the development of more effective therapies for these conditions.

InChI:InChI=1/C8H10N2/c9-8(10)6-7-4-2-1-3-5-7/h1-5H,6H2,(H3,9,10)

Upstream product

• 140-29-4 phenylacetonitrile 
• 10602-65-0 phenyl-thioacetic acid O-ethyl ester 
• 2510-30-7 3-Amino-4-phenylisoxazol-5-one 
• 4971-77-1 ethyl 2-phenylethanimidoate 
• 23589-80-2 3-benzyl-1,2,4-oxadiazol-5(4H)-one 
• 10034-85-2 hydrogen iodide 
• 62-53-3 aniline 
• 75-05-8 acetonitrile 
• 98-95-3 nitrobenzene 
• 7664-41-7 ammonia 
• 5442-34-2 ethyl 2-phenylacetimidate hydrochloride 

Downstream Products

• 124121-41-1 N,N,N'-tris-(4-nitro-benzenesulfenyl)-2-phenyl-acetamidine 
• 872826-79-4 4-amino-2-benzyl-pyrimidine-5-carbonitrile 
• 92580-36-4 (2-benzyl-6-oxo-1,6-dihydro-pyrimidin-5-yl)-acetic acid ethyl ester 
• 49773-40-2 N-chloro-2-phenyl-acetamidine 
• 55365-66-7 N-(3,4-Dichlorstyrylsulfonyl)-phenylacetamidin 
• 79899-29-9 2-amino-3-phenyl-5-nitropyridine 
• 152971-58-9 (4,6-Dibenzyl-5H-[1,3,5,2]triazaphosphinin-2-yl)-dimethyl-amine 
• 7664-41-7 ammonia 
• 103-81-1 Benzeneacetamide 
• 73077-49-3 N-cyano-2-phenyl-acetamidine 

Relevant academic research and scientific papers

Novel Allosteric Inhibitors of Deoxyhypusine Synthase against Malignant Melanoma: Design, Synthesis, and Biological Evaluation

Based on the novel allosteric site of deoxyhypusine synthase (DHPS), two series of 30 novel 5-(2-methoxyphenoxy)-2-phenylpyrimidin-4-amine derivatives as DHPS inhibitors were designed and synthesized. Among them, compound8m, with the best DHPS inhibitory potency (IC50= 0.014 μM), exhibited excellent inhibition against melanoma cells, which was superior to that of GC7. Besides, molecular docking and molecular dynamics (MD) simulations further proved that compound8mwas tightly bound to the allosteric site of DHPS. Flow cytometric analysis and enzyme-linked immunosorbent assay (ELISA) showed that compound8mcould inhibit the intracellular reactive oxygen species (ROS) level. Furthermore, by western blot analysis, compound8meffectively activated caspase 3 and decreased the expressions of GP-100, tyrosinase, eIF5A2, MMP2, and MMP9. Moreover, both Transwell analysis and wound healing analysis showed that compound8mcould inhibit the invasion and migration of melanoma cells. In thein vivostudy, the tumor xenograft model showed that compound8meffectively inhibited melanoma development with low toxicity.

Guanidine Synthesis: Use of Amidines as Guanylating Agents

The use of amidines for the tandem or one-pot synthesis of guanidines is reported. Guanidines are obtained by oxidative rearrangement of readily available and stable amidines into carbodiimides, followed by in situ reaction with amines. The protocol can be executed under mild reaction conditions (30°C), in a green solvent (dimethyl carbonate). The amine scope is broad, including sterically hindered, oxidation-sensitive and chiral amines. Examples for the synthesis of both acyclic and cyclic guanidines are provided. 2-Propoxyphenyl iodide (2-PrOPhI) by-product, generated from the oxidant [N-(p-toluenesulfonyl)imino](2-propoxyphenyl)iodinane (2-PrOPhINTs), can be isolated in high yields making regeneration of the hypervalent iodine reagent possible. The utility and greenness of the synthetic method versus the state-of-the-art is demonstrated by a new route towards the antihypertensive drug Pinacidil. The process mass intensity (PMI) of the new route is only 24% of the classical one.

Novel pyrimidoazepine analogs as serotonin 5-HT2A and 5-HT 2C receptor ligands for the treatment of obesity

Obesity is one of the most serious public health problems worldwide in the 21st century. Current therapeutic treatment for obesity is mostly focused on preventive measures involving dietary control and physical exercises in combination with anti-obesity m

Selective N-alkylation of amines using nitriles under hydrogenation conditions: Facile synthesis of secondary and tertiary amines

Nitriles were found to be highly effective alkylating reagents for the selective N-alkylation of amines under catalytic hydrogenation conditions. For the aromatic primary amines, the corresponding secondary amines were selectively obtained under Pd/C-catalyzed hydrogenation conditions. Although the use of electron poor aromatic amines or bulky nitriles showed a lower reactivity toward the reductive alkylation, the addition of NH4OAc enhanced the reactivity to give secondary aromatic amines in good to excellent yields. Under the same reaction conditions, aromatic nitro compounds instead of the aromatic primary amines could be directly transformed into secondary amines via a domino reaction involving the one-pot hydrogenation of the nitro group and the reductive alkylation of the amines. While aliphatic amines were effectively converted to the corresponding tertiary amines under Pd/C-catalyzed conditions, Rh/C was a highly effective catalyst for the N-monoalkylation of aliphatic primary amines without over-alkylation to the tertiary amines. Furthermore, the combination of the Rh/C-catalyzed N-monoalkylation of the aliphatic primary amines and additional Pd/C-catalyzed alkylation of the resulting secondary aliphatic amines could selectively prepare aliphatic tertiary amines possessing three different alkyl groups. According to the mechanistic studies, it seems reasonable to conclude that nitriles were reduced to aldimines before the nucleophilic attack of the amine during the first step of the reaction.

Heterocyclic compounds

The inventive subject matter relates to compounds, pharmaceutical compositions, and kits containing a heterocyclic compound represented by the formula (I) wherein R is an alkyl group optionally having substituent(s) etc., X is an amino group optionally having substituent(s), Y1 and Y2 are nitrogen atoms etc., an isomer or solvate thereof or a pharmaceutically acceptable salt thereof as an active ingredient.

Evolution of anti-HIV drug candidates. Part 1: From α-Anilinophenylacetamide (α-APA) to imidoyl thiourea (ITU)

Stemming from work on a previous clinical candidate, loviride, and other α-APA derivatives, a new series of potent non-nucleoside reverse transcriptase inhibitors (NNRTIs) has been synthesized. The ITU analogues, which contain a unique diarylated imidoyl thiourea, are very active in inhibiting both wild-type and clinically important mutant strains of HIV-1.

Evolution of anti-HIV drug candidates. Part 2: Diaryltriazine (DATA) analogues

A synthesis program directed toward improving the stability of imidoyl thiourea based non-nucleoside reverse transcriptase inhibitors (NNRTIs) led to the discovery of diaryltriazines (DATAs), a new class of potent NNRTIs. The synthesis and anti-HIV struct

Benzylimidazolines as h5-HT(1B/1D) serotonin receptor ligands: A structure-affinity investigation

Benzylimidazolines may represent a class of 5-HT(1D) ligands that has yet to be exploited. On the basis of a previous report that the 2- (substituted-benzyl)imidazoline α-adrenergic agonist oxymetazoline (8) binds with high affinity at calf brain 5-HT(1D) receptors, we explored the structure-affinity relationships of a series of related derivatives. Each of the aromatic substituents was removed and then reinstated in a systematic manner to determine the influence of the individual substituents on binding. It was found that all of the aromatic substituents of 8 act in concert to impart high affinity. However, although the 3-hydroxy group could be removed without significantly reducing affinity for h5-HT(1D) (i.e., human 5- HT(1Dα)) receptors, this modification reduced h5-HT(1B) (i.e., human 5- HT(1Dβ)) receptor affinity by nearly 50-fold. The 2,6-dimethyl groups also contribute to binding but seem to play a greater role for h5-HT(1B) binding than h5-HT(1D) binding. With the appropriate structural modifications, several compounds were identified that display 20- to > 100-fold selectivity for h5-HT(1D) versus h5-HT(1B) receptors. Preliminary functional data suggest that these compounds behave as agonists. Given that 5-HT(1D) agonists are currently being explored for their antimigraine action and that activation of h5-HT(1B) receptors might be associated with cardiovascular side effects, h5- HT(1D)selective agents may offer a new lead for the development of therapeutically efficacious agents.

Synthesis and rearrangement of 2-oxo-3-phenylisoxazolo[2,3-a]pyrimidines

2-Oxo-3-phenylisoxazole[2,3-a]pyrimidine derivatives were synthesized by the reaction of 3-amino-4-phenyl-5-isoxazolone with malonaldehyde tetraacetal, 3-oxobutyraldehyde diacetal, 2,4-pentanedione, and 1-phenyl-1,3-butanedione. The regioselectivity of this reaction was determined by X-ray single crystal structural analysis. Upon heating either in water or in ethanol this bicyclic system underwent a ring opening, followed by decarboxylation to yield phenylpyrimidylmethanol and phenylpyrimidyl ethers. The structures of these 2-oxoisoxazolo[2,3-a]pyrimidines and the mechanism of their rearrangement is discussed.