262368-64-9

Basic information

• Product Name: 4-(4-METHYL-PIPERIDIN-1-YLMETHYL)-PHENYLAMINE
• Synonyms: 4-(4-METHYL-PIPERIDIN-1-YLMETHYL)-PHENYLAMINE;AKOS BC-2587;TIMTEC-BB SBB011089;4-[(4-Methyl-1-piperidinyl)methyl]aniline
• CAS NO: 262368-64-9
• Molecular Formula: C13H20N2
• Molecular Weight: 204.31
• Mol File: 262368-64-9.mol

Chemical Properties

• Appearance: /
• CAS DataBase Reference: 4-(4-METHYL-PIPERIDIN-1-YLMETHYL)-PHENYLAMINE(CAS DataBase Reference)
• NIST Chemistry Reference: 4-(4-METHYL-PIPERIDIN-1-YLMETHYL)-PHENYLAMINE(262368-64-9)
• EPA Substance Registry System: 4-(4-METHYL-PIPERIDIN-1-YLMETHYL)-PHENYLAMINE(262368-64-9)

Safety Data

• Hazard Codes: Xi
• HazardClass: IRRITANT
• Hazardous Substances Data: 262368-64-9(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
4-(4-METHYL-PIPERIDIN-1-YLMETHYL)-PHENYLAMINE is used as a building block for the synthesis of various drugs and chemicals. Its unique structure allows it to be a key component in the development of new medications.
Used in Organic Synthesis:
4-(4-METHYL-PIPERIDIN-1-YLMETHYL)-PHENYLAMINE serves as a reagent in organic synthesis, contributing to the creation of a wide range of chemical products.
Used in Production of Fine Chemicals:
4-(4-METHYL-PIPERIDIN-1-YLMETHYL)-PHENYLAMINE is utilized in the production of fine chemicals, which are crucial for various specialized applications.
Used in Medicinal Chemistry and Drug Discovery:
Due to its potential biological activities, this compound is of interest to researchers in medicinal chemistry and drug discovery, where it may contribute to the development of new therapeutic agents.
Used in Treatment of Diseases and Disorders:
4-(4-METHYL-PIPERIDIN-1-YLMETHYL)-PHENYLAMINE has shown promise in the treatment of various diseases and disorders, making it a valuable asset in the field of pharmacology.

Upstream product

• 626-58-4 4-methylpiperidin 
• 100-11-8 1-bromomethyl-4-nitro-benzene 

Relevant articles and documents

Semicarbazone derivative serving as caspase-3 activator and application thereof

The invention provides semicarbazone derivative serving as a caspase-3 activator and application thereof. A structural general formula of the semicarbazone derivative or pharmaceutically acceptable salts of the semicarbazone derivative is shown as a formula I shown in the description. The semicarbazone derivative disclosed by the invention can be applied to preparing of medicine for treating or preventing cancer diseases and other hyperplastic diseases; thus, treating or preventing the cancer diseases and other hyperplastic diseases, and the semicarbazone derivative has an excellent application prospect in the aspect of developing antineoplastic medicine.

Identification and biological evaluation of novel benzothiazole derivatives bearing a pyridine-semicarbazone moiety as apoptosis inducers via activation of procaspase-3 to caspase-3

Three series of compounds were designed, synthesized and evaluated for their in vitro anticancer activity against a procaspase-3 over-expression cancer cell line (U937) and a procaspase-3 no-expression cancer cell line (MCF-7) to rule out off-target effects. Biological evaluation led to the identification of a series of benzothiazole derivatives bearing a pyridine-semicarbazone moiety, 8j and 8k, with promising anticancer activity and remarkable selectivity. Further mechanism studies revealed that compounds 8j and 8k could induce apoptosis of cancer cells by activating procaspase-3 to caspase-3, and compound 8k exhibited the strongest procaspase-3 activation activity. Structure-activity relationships (SARs) revealed that the presence of benzothiazole and an N,N,O-donor set is crucial for the anticancer activity and selectivity, and reducing the electron density of the N,N,O-donor set results in a dramatic decline in the anticancer activity and selectivity. Furthermore, toxicity evaluation (zebrafish) in vivo and metabolic stability studies (human, rat and mouse liver microsomes) were performed to provide reliable guidance for further PK/PD studies in vivo.

Design, synthesis and antiproliferative activity of novel benzothiazole derivatives conjugated with semicarbazone scaffold

Two series of novel benzothiazole derivatives conjugated with semicarbazone scaffold were designed and synthesized through a structure-based molecular hybridization strategy. All the target compounds were evaluated for their cytotoxicity in vitro against three cancer cell lines (HT-29, MKN-45 and H460) by standard MTT assay. The pharmacological results indicated that seven compounds (17h-n) exhibited comparable or even better antiproliferative activity in comparison with reference drugs Sorafenib and PAC-1. Particularly, compound 17i displayed remarkable cytotoxicity against tested three cancer cell lines with IC50 values of 0.84, 0.06 and 0.52 μM, which were 4.3-, 36.6-, 4.2-folds more potent than Sorafenib and 1.2-, 13.7-, 6.9-times more active than PAC-1, respectively.

Design, synthesis, and structure-activity relationships of novel benzothiazole derivatives bearing the ortho-hydroxy N-carbamoylhydrazone moiety as potent antitumor agents

A series of novel benzothiazole derivatives bearing the ortho-hydroxy N-carbamoylhydrazone moiety were designed and synthesized and their cytotoxic activities against five cancer cell lines (NCI-H226, SK-N-SH, HT29, MKN45, and MDA-MB-231) were screened in vitro. Most of them showed moderate to excellent activity against all the tested cell lines. Among them, compounds 15g (procaspase-3 EC50 = 1.42 μM) and 16b (procaspase-3 EC 50 = 0.25 μM) exhibited excellent antitumor activity with IC 50 values ranging from 0.14 μM to 0.98 μM against all cancer cell lines, which were 1.8-8.7 times more active than the first procaspase activating compound (PAC-1) (procaspase-3 EC50 = 4.08 μM). The structure-activity relationship (SAR) analyses indicated that the introduction of a lipophilic group (a benzyloxy or heteroaryloxy group) at the 4-position of the 2-hydroxy phenyl ring was beneficial to antitumor activity, and the presence of substituents containing nitrogen that are positively charged at physiological pH could also improve antitumor activity. It was also confirmed that the steric effect of the 4-position substituent of the benzyloxy group had a significant influence on cytotoxic activity.

Synthesis and biological evaluation of benzothiazole derivatives bearing the ortho-hydroxy-N-acylhydrazone moiety as potent antitumor agents

A novel series of benzothiazole derivatives bearing the ortho-hydroxy-N-acylhydrazone moiety were designed, synthesized, and evaluated for their procaspase-3 kinase activation activities and antiproliferative activities against five cancer cell lines (NCI-H226, SK-N-SH, HT29, MKN-45, and MDA-MB-231). Most target compounds showed moderate to excellent cytotoxic activity against all five tested cancer lines. The most promising compound 18e (procaspase-3 EC50- 0.31μM) with IC50 values ranging from 0.24 to 0.92 μM against all tested cell lines was 4.24-12.2 times more active than PAC-1 (procaspase-3 EC50 - 0.41 μM). Structure-activity relationship studies indicated that the phenyl group on the 2-hydroxyphenyl ring (moiety A) was critical for pharmacological activity in vitro. In addition, introduction of a benzyloxyl group on moiety A and a mono-electron-withdrawing group at the 4-position of the benzyloxyl group were more favorable for antitumor activity. Moreover, reduction of the electron density in the phenyl ring of the benzyloxy group led to a dramatic decrease in the procaspase-3 kinase activation activity. -

BETA-KETOAMIDE COMPOUNDS HAVING AN MCH-ANTAGONISTIC EFFECT AND MEDICAMENTS CONTAINING SAID COMPOUNDS

The invention relates to β-ketoamide compounds of general formula (I) wherein the groups and radicals A, B, b, X, Y, Z, R1, R2, R3, R5a and R5b have the designations cited in patent claim 1. The invention also relates to medicaments containing at least one inventive amide. As a result of the MCH receptor antagonistic activity, the inventive medicaments are suitable for treating metabolic disorders and/or eating disorders, especially adipositas, bulimia, anorexia, hyperphagia and diabetes.

Beta-ketoamide compounds with MCH antagonistic activity

Compounds of formula I wherein the groups and residues A, B, b, X, Y, Z, R1, R2, R3, R5a and R5b have the meanings given in claim 1. The invention further relates to pharmaceutical compositions containing at least one amide according to the invention. As a result of their MCH-receptor antagonistic activity the pharmaceutical compositions according to the invention are suitable for the treatment of metabolic disorders and/or eating disorders, particularly obesity, bulimia, anorexia, hyperphagia, and diabetes.

Substituted indolines which inhibit receptor tyrosine kinases

Indolinones of the formula having an inhibitory effect on receptor tyrosine kinases and cyclin/CDK complexes, as well as on the proliferation of endothelial cells and various tumor cells. Exemplary are: (a) 3-Z-[1-(4-(piperidin-1-yl-methyl)-anilino)-1-phenyl-methylene]-6-ethoxycarbonyl-2-indolinone, (b) 3-Z-[(1-(4-(piperidin-1-yl-methyl)-anilino)-1-phenyl-methylene]-6-carbamoyl-2-indolinone, and (c) 3-Z-[1-(4-(piperidin-1-yl-methyl)-anilino)-1-phenyl-methylene]-6-metboxycarbonyl-2-indolinone.

Substituted indolinones with kinase inhibitory activity

Substituted indolinones of general formula having effect on various kinases and cycline/CDK complexes and on the proliferation of various tumour cells. Exemplary compounds are: 3-Z-[1-(4-(N-Benzyl-N-methyl-aminomethyl)-phenylamino)-1-methyl-methylene]-5-a