65300-53-0

Usage

Uses

Used in Pharmaceutical Industry:
4-[2-(4-NITROPHENOXY)ETHYL]MORPHOLINE is used as a building block for the synthesis of complex molecules with potential pharmacological applications. Its biological activities, such as antifungal, antibacterial, and antiparasitic properties, make it a promising candidate for the development of new drugs.
Used in Agrochemical Industry:
4-[2-(4-NITROPHENOXY)ETHYL]MORPHOLINE is used as an active ingredient or intermediate in the development of agrochemicals, such as pesticides and fungicides, due to its antifungal and antibacterial properties. These agrochemicals can help protect crops from various diseases and pests, ensuring higher yields and better quality produce.
Used in Organic Synthesis:
4-[2-(4-NITROPHENOXY)ETHYL]MORPHOLINE is used as a versatile intermediate in organic synthesis for the preparation of various organic compounds. Its unique structure allows for further functionalization and modification, enabling the synthesis of a wide range of molecules with diverse applications in different industries.

InChI:InChI=1/C12H16N2O4/c15-14(16)11-1-3-12(4-2-11)18-10-7-13-5-8-17-9-6-13/h1-4H,5-10H2

Upstream product

• 3240-94-6 N-(2-chlorethyl)morpholine 
• 100-02-7 4-nitro-phenol 
• 622-40-2 2-(morpholin-4-yl)ethanol 
• 350-46-9 4-Fluoronitrobenzene 
• 100-00-5 4-chlorobenzonitrile 
• 3647-69-6 4-(2-chloroethyl)morpholine hydrochride 
• 110-91-8 morpholine 
• 16365-27-8 2-(4-nitrophenoxy)ethanol 
• 3383-72-0 1-(2-chloroethoxy)-4-nitrobenzene 
• 13288-06-7 1-(2-bromoethoxy)-4-nitrobenzene 
• 1124-31-8 potassium 4-nitrophenolate 

Downstream Products

• 52481-41-1 4-(2-morpholinoethoxy)aniline 
• 109473-83-8 [4-(2-morpholino-ethoxy)-phenyl]-carbamic acid methyl ester; hydrochloride 
• 101956-11-0 [4-(2-morpholino-ethoxy)-phenyl]-carbamic acid heptylester; hydrochloride 
• 950769-61-6 2-(4-aminophenyl)-7-(2-morpholin-4-ylethoxy)imidazo[2,1-b][1,3]benzothiazole 
• 950769-60-5 4-(2-((2-(4-nitrophenyl)benzo[d]imidazo[2,1-b]thiazol-7-yl)oxy)ethyl)morpholine 

Relevant academic research and scientific papers

Synthesis and biological evaluation of diaryl urea derivatives as FLT3 inhibitors

As a class III receptor tyrosine kinase (RTK), FMS-like tyrosine kinase 3 (FLT3) is always overexpressed in many cases of acute leukemia. This paper studies the structure-based synthesis and biological evaluation of diaryl urea derivatives as FLT3 inhibitors. Encouragingly, compounds 15b, 16b, 24a, and 24c showed excellent biological activities in a low nanomolar range. In particular, compound 16b demonstrated significant inhibitory potency against FLT3-ITD (IC50 = 5.60 nM) and better antiproliferative activity than quizartinib against MV4-11 cell line (IC50 = 0.176 nM). It is indicated that compound 16b for the treatment of acute myeloid leukemia could be very promising.

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.

Optimised synthesis of a nitroCBI hypoxia-activated prodrug with substantial anticancer activity

An optimised synthesis of a hypoxia-activated anticancer prodrug related to the duocarmycin family of natural products is described. The improved 10-step synthesis increases the overall yield from 4.4% to over 40% while requiring just 2 chromatography-bas

Discovery of 4-piperazinyl-2-aminopyrimidine derivatives as dual inhibitors of JAK2 and FLT3

Hybridization strategy is an effective strategy to obtain multi-target inhibitors in drug design. In this study, we assembled the pharmacophores of momelotinib and tandutinib to get a series of 4-piperazinyl-2-aminopyrimidine derivatives. All compounds were tested for the inhibition of JAK2 and FLT3 enzymes, of which, compounds with potent enzyme activities were assayed for antiproliferative activities against three cancer cell lines (HEL, MV4-11, and HL60). The structure-activity relationship studies were conducted through variations in two regions, the “A” phenyl ring and “B” phenyl ring. Compound 14j showed the most balanced in vitro inhibitory activity against JAK2 and FLT3 (JAK2 IC50 = 27 nM, FLT3 IC50 = 30 nM), and it also showed potent inhibition against the above tested cell lines. In the cellular context, 14j strongly induced apoptosis by arresting cell cycle in the G1/S phase, and was selected as a promising JAK2/FLT3 dual inhibitor.

Palladium catalyzed chloroethoxylation of aromatic and heteroaromatic chlorides: An orthogonal functionalization of a chloroethoxy linker

A novel disconnection based on cross-coupling chemistry was designed to access pharmaceutically relevant aryl-aminoethyl ethers. The developed palladium-catalyzed functionalization of aryl- and heteroaryl chlorides with a sodium tetrakis-(2-chloroethoxy) borate salt is orthogonal to the simple nucleophilic replacement of the chloro function of the ethylene linker. The transformation enables efficient 2-chloroethoxylation in the absence of an additional external base. Subsequent amine substitution of the alkyl halide affords 2-aminoethoxy arenes. The applicability of this method was demonstrated through the synthesis of various aryl- and heteroaryl-alkyl ethers, including the intermediates of marketed drug molecules.

Synthesis and biological evaluation of morpholine-substituted diphenylpyrimidine derivatives (Mor-DPPYs) as potent EGFR T790M inhibitors with improved activity toward the gefitinib-resistant non-small cell lung cancers (NSCLC)

Potential new EGFRT790M inhibitors comprised of structurally modified diphenylpyrimidine derivatives bearing a morpholine functionality (Mor-DPPYs) were used to improve the activity and selectivity of gefitinib-resistant non-small cell lung cancer (NSCLC) treatment. This led to the identification of inhibitor 10c, which displayed high activity against EGFRT790M/L858R kinase (IC50?=?0.71?nM) and repressed H1975?cell replication harboring EGFRT790M mutations at a concentration of 0.037?μM. Inhibitor 10c demonstrated high selectivity (SI?=?631.9) for T790M-containing EGFR mutants over wild type EGFR, suggesting that it will cause less side effects. Moreover, this compound also shows promising antitumor efficacy in a murine EGFRT790M/L858R-driven H1975 xenograft model without affecting body weight. This study provides new potential lead compounds for further development of anti-NSCLC drugs.

Design, synthesis, biological evaluation and molecular docking studies of novel 3-aryl-4-anilino-2H-chromen-2-one derivatives targeting ERα as anti-breast cancer agents

The estrogen receptor (ER) has played an important role in breast cancer development and progression and is a central target for anticancer drug discovery. In order to develop novel selective ERα modulators (SERMs), we designed and synthesized 18 novel 3-aryl-4-anilino-2H-chromen-2-one derivatives based on previously reported lead compounds. The biological results indicated that most of the compounds presented potent ERα binding affinity and possessed better anti-proliferative activities against MCF-7 and Ishikawa cell lines than the positive control tamoxifen. The piperidyl substituted compounds such as 16d and 18d demonstrated strong ERα binding affinities and excellent anti-proliferative activities respectively. Compound 18d displayed the most potent ERα binding affinity with RBA value of 2.83%, while 16d exhibited the best anti-proliferative activity against MCF-7 cells with IC50 value of 4.52?±?2.47?μM. Further molecular docking studies were also carried out to investigate binding pattern of the newly synthesized compounds with ERα. All these results together with the structure–activity relationships (SARs) indicated that these 3-aryl-4-anilino-2H-chromen-2-one derivatives with basic side chain could serve as promising leads for further optimization as novel SERMs.

With anti-tumor activity of the benzamide compound and its preparation method and application

The invention discloses a benzamide compound with antitumor activity as well as a preparation method and application thereof. The structural formula of the compound is shown in the specification, wherein in the structural formula, R1 is hydrogen or halogen; R2 is alkoxy with carbon number of 1-4; the terminal of R2 is replaced by tert-amido; R2 is linked to the para-position of benzamide via oxygen atoms; R3 is one of hydroxyl or methoxyl; R4 is the other one of hydroxyl or methoxyl. The compound has good tumor cell inhibiting activity in vitro and can be used for preparing antitumor drugs, especially anti-hepatoma drugs and anti-breast cancer drugs. The preparation method of the benzamide compound, provided by the invention, has the advantages that the raw materials are accessible, the reaction conditions are mild, the reaction process is simple to operate, and the used reagent is cheap.

Novel pazopanib derivatives and pharmaceutical composition comprising the same

The present invention relates to novel pazopanib derivatives or a salt thereof having inhibition activities of angiogenesis and epidermal growth factors at the same time, and to a pharmaceutical composition comprising the same as an active ingredient. The pazopanib derivatives have inhibition activities of angiogenesis and epidermal growth factors at the same time unlike pazopanib, thereby more effectively treating and preventing EGFR-related cancer diseases such as lung cancer, colon cancer or breast cancer through a multiple aim target, and effectively treating and preventing non-small-cell lung cancer which Iressa or Tarceva cannot have an effect on.COPYRIGHT KIPO 2017

Five-And-Six-Membered Heterocyclic Compound, And Preparation Method, Pharmaceutical Composition And Use Thereof

A five-and-six-membered heterocyclic compound as represented by general formula I, pharmaceutically acceptable salt, metabolite, metabolic precursors or drug precursors thereof, preparation method, pharmaceutical composition, and use thereof; the five-and-six-membered heterocyclic compound has activity as a Janus kinase (JAK) inhibitor, and can be used to prepare drugs for treating diseases caused by the abnormal activity of kinase, such as cell proliferation diseases like cancer.