51013-67-3

Usage

Uses

Used in Pharmaceutical Industry:
4-(Morpholinomethyl)aniline is used as a key intermediate in the synthesis of tyrosine kinase inhibitors for the pharmaceutical industry. These inhibitors play a crucial role in the treatment of various diseases, including cancer, by targeting and inhibiting the activity of tyrosine kinase enzymes, which are often overexpressed or mutated in disease states.
Used in Chemical Synthesis:
4-(Morpholinomethyl)aniline serves as a valuable building block in the synthesis of a wide range of organic compounds, such as pharmaceuticals, agrochemicals, and other specialty chemicals. Its unique structural features allow for further functionalization and modification, enabling the development of novel molecules with diverse applications.
Used in Research and Development:
In the field of research and development, 4-(Morpholinomethyl)aniline is utilized as a starting material or a reagent in the design and synthesis of new chemical entities. Its versatility and reactivity make it an attractive candidate for exploring new chemical reactions and developing innovative molecular structures with potential applications in various industries.

InChI:InChI=1/C11H16N2O/c12-11-3-1-10(2-4-11)9-13-5-7-14-8-6-13/h1-4H,5-9,12H2

Upstream product

• 110-91-8 morpholine 
• 78584-38-0 p-N-Sulfinylamino-benzylchlorid 
• 78584-40-4 p-N-Sulfinylamino-benzylbromid 
• 6425-46-3 4-(4-nitrobenzyl)morpholine 
• 1344-13-4 tin(I) chloride 
• 15795-42-3 N-sulfinyl-4-methylaniline 
• 100-11-8 1-bromomethyl-4-nitro-benzene 
• 110-89-4 piperidine 
• 144-55-8 sodium hydrogencarbonate 
• 62-23-7 4-nitro-benzoic acid 
• 7439-89-6 iron 
• 7440-05-3 palladium 
• 7440-44-0 pyrographite 
• 90754-91-9 4-(4-nitrobenzyl)morpholine hydrochloride 

Downstream Products

• 109562-90-5 benzaldehyde-(4-morpholinomethyl-phenylhydrazone) 
• 108176-90-5 1-<4-(N-morpholinomethyl)phenylaminomethyl>benzimidazole 
• 108176-88-1 2-[(4-Morpholin-4-ylmethyl-phenylamino)-methyl]-isoindole-1,3-dione 
• 108176-82-5 3-<4-(N-morpholinomethyl)phenyl-aminomethyl>benzoxazolin-2-one 
• 108176-87-0 3-<4-(morpholinomethyl)phenylaminomethyl>benzoxazolin-2-thione 
• 108176-91-6 3-<4-(N-morpholinomethyl)phenylaminomethyl>benzothiazolin-2-thione 
• 108176-81-4 1,3-bis<4-(N-morpholinomethyl)phenylaminomethyl>benzimidazoline-2-thione 
• 118794-37-9 *0.5H₂O 
• 108176-84-7 6-nitro-3-<4-(N-morpholinomethyl)phenylaminomethyl>benzoxazolin-2-one 
• 909871-05-2 4-(4-isothiocyanatobenzyl)-morpholine 
• 909871-62-1 2,4-bis(allyloxy)-5-(but-2ynyl)-N-[4-(morpholin-4-ylmethyl)phenyl]benzamide 
• 503183-21-9 4-[(4-(morpholin-4-ylmethyl)phenyl)hydrazono]-4H-pyrazole-3,5-diamine 
• 1119899-57-8 5-(6-formylquinolin-4-yl)-N-(4-(morpholinomethyl)phenyl)thiophene-2-carboxamide 
• 1143018-50-1 4-(4-ethylthiophen-2-yl)-N-(4-(morpholinomethyl)phenyl)-7-tosyl-7H-pyrrolo[2,3-d]pyrimidin-2-amine 

Relevant academic research and scientific papers

Discovery of novel 2,4‐dianilinopyrimidine derivatives containing 4‐(Morpholinomethyl)phenyl and n‐substituted benzamides as potential fak inhibitors and anticancer agents

Focal adhesion kinase (FAK) is responsible for the development and progression of various malignancies. With the aim to explore novel FAK inhibitors as anticancer agents, a series of 2,4‐ dianilinopyrimidine derivatives 8a–8i and 9a–9g containing 4‐(morpholinomethyl)phenyl and N‐ substituted benzamides have been designed and synthesized. Among them, compound 8a dis-played potent anti‐FAK activity (IC50 = 0.047 ± 0.006 μM) and selective antiproliferative effects against H1975 (IC50 = 0.044 ± 0.011 μM) and A431 cells (IC50 = 0.119 ± 0.036 μM). Furthermore, compound 8a also induced apoptosis in a dose‐dependent manner, arresting the cells in S/G2 phase and inhibiting the migration of H1975 cells, all of which were superior to those of TAE226. The docking analysis of compound 8a was performed to elucidate its possible binding modes with FAK. These results established 8a as our lead compound to be further investigated as a potential FAK inhibitor and anticancer agent.

Development of an efficient synthesis of the pyrrolquinolone PHA-529311

An efficient synthesis of N-(4-chlorobenzyl)-2-(2-hydroxyethyl)-8- (morpholin-4-ylmethyl)-6-oxo-6H-pyrrol[3.2.1-ij]quinoline-5-carboxamide (5) was developed. The route was chosen due to its reasonable length (seven steps), solubility of intermediates, and capabilities of the pilot and production facilities. The critical transformations in this route were the selective iodination of an aniline, formation of the quinolone, and Sonogashira coupling/pyrrole formation. In addition, removal of residual palladium and copper from the penultimate and final products, which was of lower concern during the discovery phase of development, became a difficult process chemistry issue on scale-up.

PYRIMIDINE COMPOUND, PREPARATION METHOD THEREOF AND MEDICAL USE THEREOF

The present invention discloses a pyrimidine compound, a preparation method thereof and a medical use thereof. Specifically, the present invention discloses a pyrimidine compound represented by formula (I), pharmaceutically acceptable salts thereof, a preparation method thereof, and a use thereof as a cyclin-dependent kinase 9 (CDK9) inhibitor, particularly for the treatment of cancer. The definition of each group in formula (I) is the same as that in the specification.

Noncovalent EGFR T790M/L858R inhibitors based on diphenylpyrimidine scaffold: Design, synthesis, and bioactivity evaluation for the treatment of NSCLC

A series of diphenylpyrimidine derivatives bearing a hydroxamic acid group was designed and synthesized as noncovalent EGFRT790M/L858R inhibitors to improve the biological activity and selectivity. One of the most promising compound 9d effectively interfered EGFRT790M/L858R binding with ATP and suppressed the proliferation of H1975 cells with IC50 values of 1.097 nM and 0.09777 μM, respectively. Moreover, compound 9d also not only exhibited a high selective index of 43.4 for EGFRT790M/L858R over the wild-type and 10.9 for H1975 cells over A431, but also exhibited low toxicity against the normal HBE cells (IC50 > 20 μΜ). In addition, the action mechanism validated that compound 9d effectively inhibited cell migration and promoted cell apoptosis by blocking cell cycle at G2/M stage. Furthermore, the target dose-dependently downregulated the expression of p-EGFR and arrested the activation of downstream Akt and ERK in H1975. All these studies provide important clues for the discovery of potent noncovalent EGFRT790M/L858R inhibitors.

Synthesis and biological activity of thieno[3,2-d]pyrimidines as potent JAK3 inhibitors for the treatment of idiopathic pulmonary fibrosis

Idiopathic pulmonary fibrosis (IPF) is a serious and fatal lung disease, with a median survival of only 3–5 years from diagnosis. Janus kinase 3 (JAK3) has a well-established role in the pathogenesis of various autoimmune diseases, including rheumatoid arthritis (RA) and autoimmune-related pulmonary fibrosis. In this study, through the use of a conformationally-constrained design strategy, a series of thieno[3,2-d]pyrimidines were synthesized as potent JAK3 inhibitors for the treatment of IPF. Among them, the most potent JAK3 inhibitor, namely 8e (IC50 = 1.38 nM), significantly reduced the degree of airsacculitis and fibrosis according to hematoxylin-eosin (HE) staining assay for the lung tissue in the bleomycin (BLM)-induced pulmonary fibrosis mouse model. The clear reduction of the lung collagen deposition by the determination of Masson and hydroxyproline (HYP) content also demonstrated its efficacy in the treatment of fibrosis. In addition, 8e also reduced the expression of the inflammatory markers IL-6, IL-17A, TNF-α and malondialdehyde (MDA) in lung tissue, which indicated its higher anti-inflammatory activity compared with that of the reference agents (nintedanib and gefitinib). Furthermore, it possessed low cytotoxicity against normal human bronchial epithelia (HBE) cells (IC50 > 39.0 μM) and C57BL mice. All these evaluated biological properties suggest that 8e may be a potential JAK3 inhibitor for the treatment of IPF.

Exploiting the Tolerant Region i of the Non-Nucleoside Reverse Transcriptase Inhibitor (NNRTI) Binding Pocket: Discovery of Potent Diarylpyrimidine-Typed HIV-1 NNRTIs against Wild-Type and E138K Mutant Virus with Significantly Improved Water Solubility an

Diarylpyrimidine derivatives (DAPYs) exhibit robust anti-HIV-1 potency, although they have been compromised by E138K variant and severe side-effects and been suffering from poor water solubility. In the present work, hydrophilic morpholine or methylsulfon

4-(saturated aliphatic ring-pyrimidine/pyridine substituted)amino-1H-3-pyrazol carboxamide FMS-like tyrosine kinase 3 (FLT3) inhibitor and application thereof

The invention relates to 4-(saturated aliphatic ring-pyrimidine/pyridine substituted)amino-1H-3-pyrazol carboxamide FMS-like tyrosine kinase 3 (FLT3) inhibitor, an application thereof, or pharmaceutically acceptable salt, solvate, isomer, ester, acid, met

HISTONE METHYLTRANSFERASE EZH2 INHIBITOR, PREPARATION METHOD AND PHARMACEUTICAL USE THEREOF

The invention relates to a histone methyltransferase EZH2 inhibitor, a preparation method and pharmaceutical use thereof. In particular, the invention relates to a compound represented by the general formula (I), a preparation method thereof, a pharmaceut

Synthesis, β-hematin inhibition studies and antimalarial evaluation of new dehydroxy isoquine derivatives against Plasmodium berghei: A promising antimalarial agent

Many people are affected by Malaria around the world, and the parasite is developing resistance against available drugs. Currently, isoquine and N-tert-butyl isoquine are some of the most promising antimalarial candidates that have already reached Phase I

Discovery of 4-((7H-Pyrrolo[2,3-d]pyrimidin-4-yl)amino)-N-(4-((4-methylpiperazin-1-yl)methyl)phenyl)-1H-pyrazole-3-carboxamide (FN-1501), an FLT3- and CDK-Kinase Inhibitor with Potentially High Efficiency against Acute Myelocytic Leukemia

A series of 1-H-pyrazole-3-carboxamide derivatives have been designed and synthesized that exhibit excellent FLT3 and CDK inhibition and antiproliferative activities. A structure-activity-relationship study illustrates that the incorporation of a pyrimidine-fused heterocycle at position 4 of the pyrazole is critical for FLT3 and CDK inhibition. Compound 50 (FN-1501), which possesses potent inhibitory activities against FLT3, CDK2, CDK4, and CDK6 with IC50 values in the nanomolar range, shows antiproliferative activities against MV4-11 cells (IC50: 0.008 μM), which correlates with the suppression of retinoblastoma phosphorylation, FLT3, ERK, AKT, and STAT5 and the onset of apoptosis. Acute-toxicity studies in mice show that compound 50 (LD50: 186 mg/kg) is safer than AT7519 (32 mg/kg). In MV4-11 xenografts in a nude-mouse model, compound 50 can induce tumor regression at the dose of 15 mg/kg, which is more efficient than cytarabine (50 mg/kg). Taken together, these results demonstrate the potential of this unique compound for further development into a drug applied in acute-myeloid-leukemia (AML) therapeutics.