16817-90-6

Usage

Uses

Used in Pharmaceutical Industry:
2-Amino-N-cyclohexylacetamide is used as a key intermediate in the synthesis of various pharmaceuticals for its analgesic and anti-inflammatory properties. It aids in the development of pain-relieving medications by modulating pain signals within the central nervous system.
Used in Agrochemical Industry:
Although not explicitly mentioned in the provided materials, given its utility as a building block in chemical synthesis, 2-Amino-N-cyclohexylacetamide could also be used in the agrochemical industry for the development of compounds with pesticidal or herbicidal properties, leveraging its structural and reactive characteristics to target specific pests or weeds.
Used in Neurological Disorder Treatment:
2-Amino-N-cyclohexylacetamide is used as a potential therapeutic agent for treating neuropathic pain and other neurological disorders, due to its effects on the central nervous system and its capacity to alleviate pain signals.
Used in Research and Development:
2-Amino-N-cyclohexylacetamide serves as a promising candidate for research and development in the pharmaceutical industry, where its structure and pharmacological properties are further explored to discover new applications and enhance existing treatments.

Upstream product

• 2185-00-4 1,3-oxazolidine-2,5-dione 
• 5577-68-4 cyclohexylamino-trimethyl-silane 
• 108-91-8 cyclohexylamine 
• 5373-25-1 N-(toluene-4-sulfonyl)-glycine cyclohexylamide 
• 14432-20-3 α-N-Formylamino-N'-cyclohexylacetamid 
• 666177-21-5 N-(5-methyl-1-benzotriazolecarbonyl)glycine cyclohexylamide 
• 3496-41-1 cyclohexyl carbamoylmethyl carbamic acid benzyl ester 
• 33952-53-3 cyclohexylcarbamoylmethylcarbamic acid t-butyl ester 
• 4530-20-5 BOC-glycine 

Downstream Products

• 1403957-50-5 3-(N-(2-cyclohexylamino-2-oxoethyl)-N-sulfamoyl)benzamidine 
• 1403957-51-6 3-(N-(2-cyclohexylamino-2-oxoethyl)-N-sulfamoyl)benzamidinium trifluoroacetate 
• 1372089-88-7 2-(3-cyanophenylsulfonamido)-N-cyclohexylacetamide 
• 1448524-00-2 2-(4-bromophenoxy)-N-[(cyclohexylcarbamoyl)methyl]acetamide 
• 1448524-01-3 N-[(cyclohexylcarbamoyl)methyl]-2-(4-fluorophenoxy)acetamide 
• 99976-73-5 1-cyclohexylpiperazin-2-one 

Relevant academic research and scientific papers

Glycinamide hydrochloride as a transient directing group: Synthesis of 2-benzylbenzaldehydes by C(sp3)?H arylation

Glycinamide hydrochloride as an inexpensive and commercially available transient directing group for the C(sp3)?H arylation of 2-methylbenzaldehydes is described. A series of practical 2-benzylbenzaldehydes bearing various functional groups are efficiently synthesized in satisfactory yield by this strategy. This method can also be extended to gram scale.

Amido pyrimidine compound

The invention provides an amido pyrimidine compound with a novel structure as shown in a formula (I) and a preparation method and application of the amido pyrimidine compound. The amido pyrimidine compound is a compound shown as the formula (I), or a pharmaceutically acceptable salt, hydrate, solvate, prodrug, stereoisomer or tautomer thereof and the like. The amido pyrimidine compound provided bythe invention has a relatively good proliferation inhibition effect on various cancer cells; according to the present invention, the compound has characteristics of low tumor cell inhibition concentration, significantly-improved compound activity, good tumor cell selectivity and good solubility, and is expected to be a specific drug for treatment of malignant tumor cell abnormal proliferation diseases caused by EGFR mutation.

Identification of a new series of benzothiazinone derivatives with excellent antitubercular activity and improved pharmacokinetic profiles

Nitrobenzothiazinone (BTZ) is a promising scaffold with potent activity against M. tuberculosis by inhibiting decaprenylphosphoryl-beta-d-ribose 2′-oxidase (DprE1). But unfavorable durability poses a challenge to further development of this class of agents. Herein, a series of BTZs bearing a variety of different substituents at the C-2 position were designed and synthesized. Compounds were screened for their antimycobacterial activity against Mycobacterium tuberculosis H37Ra and were profiled for metabolic stability, plasma protein-binding capacity and pharmacokinetics in vivo. In general, these new BTZs containing N-piperazine, N-piperidine or N-piperidone moiety have excellent antitubercular activity and low cytotoxicity. Several of the compounds showed improved microsomal stability and lower plasma protein-binding, opening a new direction for further lead optimization. And we obtained compound 3o, which maintained good anti-tuberculosis activity (MIC = 8 nM) and presented better in vitro ADME/T and in vivo pharmacokinetic profiles than reported BTZ compound PBTZ169, which may serve as a candidate for the treatment of tuberculosis.

Palladium-Catalyzed β-C?H Arylation of Ketones Using Amino Amide as a Transient Directing Group: Applications to Synthesis of Phenanthridinone Alkaloids

The direct arylation of aromatic and aliphatic ketones was carried out via palladium-catalyzed inert C?H bond functionalization with 2-amino-N-isopropyl-acetamide as a new catalytic transient directing group. The reaction showed excellent functional group compatibility and site selectivity. We demonstrated that α-amino amide forming N,N-bidentate coordination with Pd catalyst is more favorable for the β-arylation of ketones than α-amino acid forming N,O-bidentate coordination with Pd catalyst under relatively mild conditions. This elegant approach provides straightforward access to important structural motifs in organic and medicinal chemistry and is demonstrated here in the efficient synthesis of phenanthridinone alkaloids. (Figure presented.).

In silico and pharmacological screenings identify novel serine racemase inhibitors

d-Serine is a coagonist of the N-methyl-d-aspartate (NMDA)-type glutamate receptor and its biosynthesis is catalyzed by serine racemase (SR). The overactivation of the NMDA receptor has been implicated in the development of neurodegenerative diseases, strokes, and epileptic seizures, thus, the inhibitors of SR have potential against these pathological states. Here, we have developed novel inhibitors of SR by in silico screening and in vitro enzyme assay. The newly developed inhibitors have lower IC50 value comparing with that of malonate, one of the standard SR inhibitor. The structural features of novel inhibitors suggest the importance of central amide structure having a phenoxy substituent in their structure for the SR inhibitory activity. The present findings suggest the importance and rational development of new drugs for diseases of NMDAR overactivation.

Active site mapping of trypsin, thrombin and matriptase-2 by sulfamoyl benzamidines

The benzamidine moiety, a well-known arginine mimetic, has been introduced in a variety of ligands, including peptidomimetic inhibitors of trypsin-like serine proteases. According to their primary substrate specificity, the benzamidine residue interacts with the negatively charged aspartate at the bottom of the S1 pocket of such enzymes. Six series of benzamidine derivatives (1-73) were synthesized and evaluated as inhibitors of two prototype serine proteases, that is, bovine trypsin and human thrombin. As a further target, human matriptase-2, a recently discovered type II transmembrane serine protease, was investigated. Matriptase-2 represents an important regulatory protease in iron homeostasis by down-regulation of the hepcidin expression. Compounds 1-73 were designed to contain a fixed sulfamoyl benzamidine moiety as arginine mimetic and a linker-connected additional substructure, such as a tert-butyl ester, carboxylate or second benzamidine functionality. A systematic mapping approach was performed with these inhibitors to scan the active site of the three target proteases. In particular, bisbenzamidines, able to interact with both the S1 and S3/S4 binding sites, showed notable affinity. In branched bisbenzamidines 66-73 containing a third hydrophobic residue, opposite effects of the stereochemistry on trypsin and thrombin inhibition were observed.

Synthesis and reactions of some azolecarboxylic acid derivatives

Reaction of several azoles with phosgene or triphosgene was studied. Besides benzotriazole (previously described reaction), only indazole, 5-nitroindazole and 5-methylbenzotriazole gave the corresponding 1-azolecarbonyl chlorides 1a-d. Azoles of weak acidity (imidazole, 1,2,3-triazole, 1,2,4-triazole, benzimidazole) could not give stable acyl chlorides, while strong acidic azoles like tetrazole and 4,5,6,7- tetrachlorobenzotriazole did not react at all. Chlorides 1b-d readily reacted with alcohols, amines, amino acids and their esters like the previously described 1-benzotriazolecarboxylic acid chloride (1a), giving 1-azolecarboxylic acid esters (2) or amides (3), N-(1-azolecarbonyl)amino acids (4, 5), their esters (8, 9) or amides (10, 11). However, a significant difference was observed in the reactivity of azole derivatives 2-11 with amines, alcohols and N-protected amino acids or in their stability in acidic and basic aqueous media. Benzotriazole and methylbenzotriazole derivatives were more reactive than indazole or nitroindazole derivatives. The higher reactivity was in correlation with the shift of the IR carbonyl absorption band to higher wave numbers.