39495-15-3

Usage

Uses

Used in Urine Analysis:
N-(4-Hydroxy-2-methylphenyl)acetamide is used as a monitoring agent for o-toluidine in urine samples that have undergone enzymatic deconjugation. This application is particularly relevant in the field of toxicology and occupational health, as it aids in the detection and quantification of o-toluidine, a potentially harmful aromatic amine that can be found in the urine of individuals exposed to certain industrial chemicals or pharmaceuticals.

InChI:InChI=1/C9H11NO2/c1-6-5-8(12)3-4-9(6)10-7(2)11/h3-5,12H,1-2H3,(H,10,11)

Upstream product

• 2835-99-6 4-amino-3-methylphenol 
• 108-24-7 acetic anhydride 
• 60-35-5 acetamide 
• 120-66-1 N-(2-methylphenyl)acetamide 
• 145823-43-4 diacetyl-4-amino-3-methylphenol 
• 108-39-4 3-methyl-phenol 
• 2581-34-2 3-methyl-4-nitrophenol 

Downstream Products

• 145823-43-4 diacetyl-4-amino-3-methylphenol 
• 861797-25-3 (4-acetylamino-3-methyl-phenoxy)-acetic acid 
• 31601-41-9 N-(4-methoxy-2-methylphenyl)acetamide 
• 80838-37-5 N-{4-[2-(10-Acetyl-10H-phenothiazin-2-yl)-2-oxo-ethoxy]-2-methyl-phenyl}-acetamide 
• 57556-30-6 4-hydroxy-2,N,N,N-tetramethyl-anilinium; iodide 
• 500-85-6 indophenol 
• 41570-59-6 acetic acid-(4-ethoxy-2-methyl-anilide) 
• 176661-64-6 4-amino-N-acetyl-3-methyl-2-chlorophenol 
• 1297596-87-2 4-amino-N-acetyl-3-methyl-6-chlorophenol 
• 1297596-83-8 N-acetyl-3-methyl-1,4-benzoquinone monoimine 
• 911058-09-8 N-[4-(2-adamantan-1-yl-2-oxoethoxy)-2-methylphenyl]acetamide 
• 53136-57-5 4-(4-acetamido-3-tolyloxy)-3-nitro-5-sulfamoylbenzoic acid 
• 6705-03-9 2-Amino-5-methoxybenzoic acid 
• 102-50-1 2-methyl-4-methoxyaniline 

Relevant academic research and scientific papers

Synthesis and pharmacological evaluation of piperidine (piperazine)-amide substituted derivatives as multi-target antipsychotics

We report the optimisation of a series of novel amide-piperidine (piperazine) derivatives using the multiple ligand approach with dopamine and serotonin receptors. Of the derivatives, compound 11 exhibited high affinity for the D2, 5-HT1A, and 5-HT2A receptors, but low affinity for the 5-HT2C and histamine H1 receptors and human ether-a-go-go-related gene (hERG) channels. In vivo, compound 11 reduced apomorphine-induced climbing, MK-801-induced hyperactivity and DOI-induced head twitching without observable catalepsy, even at the highest dose tested. In addition, it exhibited suppression in a CAR test. Furthermore, in a novel object recognition task, it displayed procognition properties. Therefore, compound 11 is a promising candidate multi-target antipsychotic.

11-BETA-HYDROXYSTEROID DEHYDROGENASE INHIBITORS

There is provided a compound having Formula (I ) R1-Z-R2 wherein R1 is a group selected from optionally substituted fused polycyclic groups, substituted alkyl groups, branched alkyl groups, and optionally substituted cycioalkyl groups Z is a linker which is or comprises a carbonyl group or a isostere of a carbonyl group R2 is selected from optionally substituted aromatic rings and optionally substituted heterocyclic rings wherein (a) R2 is a 2-substituted thiophene group, and/or (b) Z is a group of the formula -C(=O)-CR3R4-X-(CR5R6)n-, wherein X is selected from NR7, S, O, S=O, and S(=O)2, wherein n is 0 or 1 and/or (c) R1 is an adamantyl group and Z is or comprises an amide group, and/or (d) R1 is an adamantyl group and Z is or comprises a group of the formula -(CR8R9)p- NR10-S(=O)2-(CR11R12)q-, wherein p is 0 or 1 and q is 0 or 1 and/or (e) R1 is an adamantyl group and Z is or comprises a group of the formula -(CR13R14)V-Y- (CR15R16)W- where Y is a heteroaryl group in which a bond in the heteroaryl ring is a isostere of a carbonyl group, wherein v is o or 1 and w is 0 or 1 ; wherein each of R3, R4, R5, R6, R8, R9, R11, R12, R13, R14, R15 and R16, are independently selected from H, hydrocarbyl and halogen, wherein each of R7 and R10 are independently selected from H and hydrocarbyl.

TRANSITION METAL COMPLEXES

A transition metal complex which is a bis-arylimine pyridine MXn complex, comprising a bis-arylimine pyridine ligand having the formula (I), wherein R1-R5, R7-R9, R12 and R14 are each, independently, hydrogen, optionally substituted hydrocarbyl, an inert functional group, or any two of R1-R3 and R7-R9 vicinal to one another taken together may form a ring, and R6 is hydrogen, optionally substituted hydrocarbyl, an inert functional group, or taken together with R7 or R4 to form a ring, R10 is hydrogen, optionally substituted hydrocarbyl, an inert functional group, or taken together with R9 or R4 to form a ring, R11 is hydrogen, optionally substituted hydrocarbyl, an inert functional group, or taken together with R12 or R5 to form a ring, R15 is hydrogen, optionally substituted hydrocarbyl, an inert functional group, or taken together with R14 or R5 to form a ring, provided that R13 and at least one of R12 and R14 are independently selected from optionally substituted C1-C30 alkyl, optionally substituted C4-C30 alkyloxy, halogen and optionally substituted C5-C20 aryl, or R13 taken together with R12 or R14 form a ring, or R12 taken together with R11 form a ring and R14 taken together with R15 form a ring, and provided that at least one of R12, R13 and R14 is optionally substituted C4-C30 alkyloxy; M is a transition metal atom in particular selected from Ti, V, Cr, Mn, Fe, Co, Ni, Pd, Rh, Ru, Mo, Nb, Zr, Hf, Ta, W, Re, Os, Ir or Pt; n matches the formal oxidation state of the transition metal atom M; and X is halide, optionally substituted hydrocarbyl, alkoxide, amide, or hydride. The transition metal complexes of the present invention, their complexes with non-coordinating anions and catalyst systems containing such complexes have good solubility in non-polar media and chemically inert non--polar solvents especially aromatic hydrocarbon solvents. The catalyst systems can be used for a wide range of (co-)oligomerization, polymerization and dimerization reactions.

Bisacetamide hydrochloride: A chemoselective and inexpensive N-acetylating reagent for aminophenols

A facile and chemoselective acetylation of aminophenols using bisacetamide hydrochloride under conventional heating and microwave irradiation has been developed. Also, a rapid method for the microwave-assisted preparation of aminophenols is described herein.

Introduction of a hydroxy group at the para position and N-iodophenylation of N-arylamides using phenyliodine(III) bis(trifluoroacetate)

The reaction of anilides with phenyliodine(III) bis(trifluoroacetate) (PIFA) in trifluoroacetic acid (TFA), TFA-CHCl3, or hexafluoroisopropyl alcohol (HFIP) is described. When the acyl group of the anilide is highly electronegative, such as trifluoroacetyl, or the phenyl group is substituted with an electron-withdrawing group, the 4-iodophenyl group is transferred from PIFA to the amide nitrogen to afford acetyldiarylamines. On the other hand, when the acyl group contains an electron-donating function, such as 4-methoxyphenyl, or the phenyl group is substituted with an electron-donating group, a trifluoroacetoxy group is transferred to the para position of the anilide aromatic ring. This group is hydrolyzed during workup to produce the corresponding phenol.

Synthesis and structure of 1,4-diazabutadiene liquid crystals

Nine 1,4-diazabutadiene compounds, Ar-N=C(R)-C(R)=N-Ar, R=H, Me; Ar= H2n+1CnO-C6H4, 2,4-(H9C4O)(Me)-C6H3 were synthesized and their liquid crystal properties were studied through thermal polarizing microscopy. The X-ray single crystal structure of compound 9 (Ar-N=C(H)-C(H)=N-Ar, Ar=2,4-(Me)(H9C4O)C6H3) was tested. It is a monoclinic crystal system, space group P21/C with the unit cell parameters: a=7.0703(3)A, b=8.674(4)A, c=18.3115(8)A, β =95.392(1)°. V=1114.57(9)A3, z=2, Dc=1.134 Mg/m3, R=0.0490,Rw=0.1237.

Synthesis, physicochemical properties, and amide-oxidation reaction of indolequinone derivatives as model compounds of novel organic cofactor TTQ of amine dehydrogenases

3,4-Disubstituted 6,7-indolequinones [1,3-dimethyl]-4-(3'-methylindol- 2'-yl)indole-6,7-dione (2), 3-methyl-4-phenylindole-6,7-dione (3), and 3,4- dimethyl-6,7-dione (4)] and a 3,7-disubstituted 4,5-indolequinone [3,7- dimethylindole-4,5-dione (5)] have been synthesized as models for the novel organic cofactor TTQ bacterial amine dehydrogenases. The substituent and structural effects on the physicochemical properties of the quinones have been investigated in detail by comparing the spectroscopic data (UV-vis, IR, 1H- and 13C-NMR), pK(a) values of the pyrrole proton, and the two-electron redox potentials with those of model compound 1 [3-methyl-4-(3'-methylindol- 2'-yl)indole-6,7-dione] previously reported (ref 5). Reactivity of each quinone in the transamination process [iminoquinone formation (k1), rearrangement to product-imine (k2) and aminophenol formation (k3)] has been investigated kinetically, revealing that the substituent and structural effects on the amine-oxidation reaction are not significant. In the aerobic catalytic oxidation of benzylamine, however, the aromatic substituents on the quinone ring play an important role to protect the quinone from the deactivation process of a Michael-type addition by the amine, making it act as an efficient turnover catalyst.

Enzyme-mediated hydrolytic studies on aminophenol diacetates

Porcine pancreatic and Candida cylindracea lipases, suspended in organic solvents and trypsin in aq. buffer have been used for selective deacylation of five different aminophenol diacetates.It has been observed that the enzyme selectively catalyses the hydrolysis of the O-acetyl group.

Comparative Toxicities and Analgesic Activities of Three Monomethylated Analogues of Acetaminophen

Three monomethylated derivatives of 4'-hydroxyacetanilide (acetaminophen) were prepared in order to compare their cytotoxic potential and analgesic activity with that of acetaminophen.Only 4'-hydroxy-methylacetanilide (N-methylacetaminophen) was devoid of cytotoxic effects to hepatic tissue of mice.Results of comparative tissue distribution studies and metabolism studies both in vivo and in vitro in mice indicate that the disposition of N-methylacetaminophen is similar to that of acetaminophen except that it is not oxidized to a toxic metabolite.In contrast, 3'-methyl-4'-hydroxyacetanilide (3-methlacetaminophen) is as hepatotoxic as acetaminophen in mice while 2'-methyl-4'-hydroxyacetanilide (2-methylacetaminophen) is less hepatotoxic.The analgesic potency of the analogues seems to parallel their hepatotoxic potential, and both activities parallel the oxidation potentials in this series of compounds.