288383-71-1

Basic information

• Product Name: 4-Chloro-6-methoxy-7-(3-piperidin-1-yl-propoxy)-quinazoline
• Synonyms: 4-Chloro-6-methoxy-7-(3-piperidin-1-yl-propoxy)-quinazoline;4-Chloro-6-methoxy-7-(3-piperidinopropoxy)quinazoline;4-Chloro-7-[3-piperidinopropoxy]-6-methoxyquinazoline
• CAS NO: 288383-71-1
• Molecular Formula: C₁₇H₂₂ClN₃O₂
• Molecular Weight: 335.82848
• Mol File: 288383-71-1.mol

Chemical Properties

• Appearance: /
• Density: 1.214
• Storage Temp.: 2-8°C
• CAS DataBase Reference: 4-Chloro-6-methoxy-7-(3-piperidin-1-yl-propoxy)-quinazoline(CAS DataBase Reference)
• NIST Chemistry Reference: 4-Chloro-6-methoxy-7-(3-piperidin-1-yl-propoxy)-quinazoline(288383-71-1)
• EPA Substance Registry System: 4-Chloro-6-methoxy-7-(3-piperidin-1-yl-propoxy)-quinazoline(288383-71-1)

Safety Data

• Hazardous Substances Data: 288383-71-1(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
4-Chloro-6-methoxy-7-(3-piperidin-1-yl-propoxy)-quinazoline is used as a targeted cancer therapy for its ability to selectively inhibit the Aurora A kinase, leading to cell cycle arrest and apoptosis in cancer cells. This makes it a promising candidate for the development of treatments for various types of cancer.

Upstream product

• 288383-74-4 6-methoxy-7-(3-piperidinopropoxy)-3,4-dihydroquinazolin-4-one 
• 574738-68-4 methyl 2-amino-5-methoxy-4-(3-(piperidin-1-yl)propoxy)benzoate 
• 927173-22-6 methyl 5-methoxy-2-nitro-4-(3-(piperidin-1-yl)propoxy)benzoate 
• 3943-74-6 4-hydroxy-3-methoxybenzoic acid methyl ester 
• 111627-40-8 methyl 4-(3-chloropropoxy)-3-methoxybenzoate 
• 214470-57-2 methyl 4-(3-chloropropoxy)-5-methoxy-2-nitrobenzoate 
• 1458-63-5 N-(3-chloropropyl)-piperidine 
• 193002-25-4 7-hydroxy-6-methoxy-3-pivaloyloxymethyl-3,4-dihydroquinazolin-4-one 
• 288383-73-3 6-methoxy-7-(3-piperidinopropoxy)-3-((pivaloyloxy)methyl)-3,4-dihydroquinazolin-4-one 
• 288383-74-4 6-methoxy-7-(3-(piperidin-1-yl)propoxy)quinazolin-4-ol 
• 1403583-41-4 methyl 3-methoxy-4-(3-(piperidin-1-yl)propoxy)benzoate 
• 110-89-4 piperidine 
• 574738-91-3 7-(3-chloropropoxy)-6-methoxy-3,4-dihydroquinazolin-4-one 
• 214470-59-4 2-Amino-4-(3-chloro-propoxy)-5-methoxy-benzoic acid methyl ester 

Downstream Products

• 387867-13-2 Tandutinib 
• 1609458-64-1 N-(3-bromophenyl)-N'-{4-[(6-methoxy-7-piperidinopropoxyquinazolin-4-yl)oxy]-phenyl}urea 
• 1609458-68-5 N-(3-bromo-phenyl)-N'-{3-methyl-4-[(6-methoxy-7-piperidinopropoxyquinazolin-4-yl)oxy]phenyl}urea hydrochloride 
• 1609458-66-3 N-(3-bromo-phenyl)-N'-{3-chloro-4-[(6-methoxy-7-piperidinopropoxyquinazolin-4-yl)oxy]phenyl}urea 
• 1227636-17-0 4-[6-methoxy-7-(3-piperidin-1-yl-propoxy)quinazolin-4-yl]piperazine-1-carboxylic acid (4-isopropoxyphenyl)-amide (L)lactate 
• 1227263-92-4 N-mesityl-2-(6-methoxy-7-(3-(piperidin-1-yl)propoxy)quinazolin-4-ylamino)benzo[d]thiazole-6-carboxamide 
• 1227263-86-6 N-(2,6-dimethylphenyl)-2-(6-methoxy-7-(3-(piperidin-1-yl)propoxy)quinazolin-4-ylamino)benzo[d]thiazole-6-carboxamide 
• 1227263-80-0 N-(2-chloro-6-methylphenyl)-2-(6-methoxy-7-(3-(piperidin-1-yl)propoxy)quinazolin-4-ylamino)benzo[d]thiazole-6-carboxamide 

Relevant articles and documents

Synthesis and antitumor activity evaluation of quinazoline derivatives bearing piperazine-1-carbodithioate moiety at C4-position

A series of quinazoline derivatives bearing piperazine-1-carbodithioate moiety at the C4-position were synthesized using piperidine and 1-bromo-3-chloropropane as starting materials via eight steps. Final compounds 8a–q and 9a–i were evaluated for their antiproliferative activity against human lung cancer A549, breast adenocarcinoma MCF-7, and colorectal cancer HCT-116 cell lines. The results showed that fourteen of twenty-six final compounds inhibited the proliferation of three cancer cell lines with IC50values less than 10?μM. When treated with a representative compound 8n, HCT-116 cells were arrested at G0/G1 phase of the cell cycle. This provided a clue to further investigation of the mechanism of action.

LACTATE SALT OF 4-[6-METHOXY-7-(3-PIPERIDIN-1-YL-PROPOXY)QUINAZOLIN-4-YL]PIPERAZINE-1-CARBOXYLIC ACID(4-ISOPROPOXYPHENYL)-AMIDE AND PHARMACEUTICAL COMPOSITIONS THEREOF FOR THE TREATMENT OF CANCER AND OTHER DISEASES OR DISORDERS

This invention provides a compound of formula (I): or a crystalline form thereof, or a pharmaceutical composition thereof, or an oral pharmaceutical dosage form thereof; processes for the synthesis or manufacture of the compound of formula (I), or a cryst

Inhibition of tumor cell growth and angiogenesis by 7-Aminoalkoxy-4- aryloxy-quinazoline ureas, a novel series of multi-tyrosine kinase inhibitors

Several regulatory and signaling molecules governing angiogenesis are targets of interest for the development of drugs in the cancer, including growth factors such as Vascular Endothelial Growth Factor (VEGF) and Platelet-Derived Growth Factor (PDGF). A series of 4-aryloxy-6,7-dimethoxyquinazolines, previously synthesized in our laboratory, has shown a nanomolar inhibition of kinase enzymatic activity of VEGFR, PDGFR and c-Kit. We have therefore studied the impact of the variation in the 7-position substitution of the quinazoline core. Substitution by aminoalkoxy chains led to new highly potent ATP-competitive inhibitors of VEGFR, PDGFR and c-Kit enzyme with IC50 values in the nanomolar range and this substitution has increased greatly antiproliferative activity on cancer cell lines (PC3, MCF7, HT29) and HUVEC (human umbilical vein endothelial cells). One of the most promising compounds (36) was assessed for its ability to limit the induction of web like network of capillary tubes by the human umbilical vascular endothelial cells (HUVEC) and for its ability to inhibit invasion.

Design and synthesis of novel 4-benzothiazole amino quinazolines Dasatinib derivatives as potential anti-tumor agents

Three series of novel 4-benzothiazole amino quinazolines Dasatinib derivatives have been designed and synthesized. The entire target compounds were investigated for their in vitro cytotoxic activity by the MTT-based assay against 6 human cancer cell lines

LACTATE SALT OF 4-(6-METHOXY-7-(3-PIPERIDIN-1-YL-PROPOXY)QUINAZOLIN-4-YL]PIPERAZINE-1-CARBOXYLIC ACID(4-ISOPROPOXYPHENYL)-AMIDE AND PHARMACEUTICAL COMPOSITIONS THEREOF FOR THE TREATMENT OF CANCER AND OTHER DISEASES OR DISORDERS

This invention provides a compound of formula (I): or a crystalline form thereof, or a pharmaceutical composition thereof, or an oral pharmaceutical dosage form thereof; processes for the synthesis or manufacture of the compound of formula (I), or a crystalline form thereof, or a pharmaceutical composition thereof, or an oral pharmaceutical dosage form thereof; and the use of said compound, or a crystalline form thereof, or a pharmaceutical composition thereof, or an oral pharmaceutical dosage form thererof, for the treatment of patients suffering from or subject to diseases, disorders or conditions involving cell survival, proliferation, and migration, including cardiovascular disease (e.g., arteriosclerosis and vascular reobstruction), cancer, (e.g., AML and malignant glioma) glomerulosclerosis, fibrotic disease and inflammation.

Improved synthesis of substituted 6,7-dihydroxy-4-quinazolineamines: Tandutinib, erlotinib and gefitinib

The synthesis of three substituted 6,7-dihydroxy-4-quinazolineamines: tandutinib (1), erlotinib (2) and gefitinib (3) in improved yields is reported. The intermediates were characterized by NMR and the purities determined by HPLC.

QUINAZOLINE DERIVATIVES AS ANGIOGENESIS INHIBITORS

The invention relates to the use of compounds of the formula I: wherein ring C is an 8, 9, 10, 12 or 13-membered bicyclic or tricyclic moiety which optionally may contain 1-3 heteroatoms selected independently from O, N and S; Z is -O-, -NH-, -S-, -CH2- or a direct bond; n is 0-5; m is 0-3; R represents hydrogen, hydroxy, halogeno, cyano, nitro, trifluoromethyl, C1-3alkyl, C1-3alkoxy, C1-3alkylsulphanyl, -NRR (wherein R and R, which may be the same or different, each represents hydrogen or C1-3alkyl), or RX- (wherein X and R are as defined herein; R represents hydrogen, oxo, halogeno, hydroxy, C1-4alkoxy, C1-4alkyl, C1-4alkoxymethyl, C1-4alkanoyl, C1-4haloalkyl, cyano, amino, C2-5alkenyl, C2-5alkynyl, C1-3alkanoyloxy, nitro, C1-4alkanoylamino, C1-4alkoxycarbonyl, C1-4alkylsulphanyl, C1-4alkylsulphinyl, C1-4alkylsulphonyl, carbamoyl, N-C1-4alkylcarbamoyl, N,N-di(C1-4alkyl)carbamoyl, aminosulphonyl, N-C1-4alkylaminosulphonyl, N,N-di(C1-4alkyl)aminosulphonyl, N-(C1-4alkylsulphonyl)amino, N-(C1-4alkylsulphonyl)-N-(C1-4alkyl)amino, N,N-di(C1-4alkylsulphonyl)amino, a C3-7alkylene chain joined to two ring C carbon atoms, C1-4alkanoylaminoC1-4alkyl, carboxy or a group RX (wherein X and R are as defined herein); and salts thereof, in the manufacture of a medicament for use in the production of an antiangiogenic and/or vascular permeability reducing effect in warm-blooded animals, processes for the preparation of such compounds, pharmaceutical compositions containing a compound of formula I or a pharmaceutically acceptable salt thereof as active ingredient and compounds of formula I. The compounds of formula I and the pharmaceutically acceptable salts thereof inhibit the effects of VEGF, a property of value in the treatment of a number of disease states including cancer and rheumatoid arthritis.

Discovery of a New Class of Anilinoquinazoline Inhibitors with High Affinity and Specificity for the Tyrosine Kinase Domain of c-Src

Deregulated activity of the nonreceptor tyrosine kinase c-Src is believed to result in signal transduction, cytoskeletal and adhesion changes, ultimately promoting a tumor-invasive phenotype. We report here the discovery of a new class of anilinoquinazoline inhibitors with high affinity and specificity for the tyrosine kinase domain of the c-Src enzyme. Special attention was directed toward finding inhibitors selective against KDR tyrosine kinase in order to ensure that the in vivo profile of a specific Src inhibitor could be determined. The 4-aminobenzodioxole quinazoline series gave compounds with excellent potency and selectivity. The most interesting compounds were evaluated in vivo and displayed good pharmacokinetics following oral dosing. Compounds such as the aminobenzodioxoles were shown to be potent inhibitors of tumor growth in a c-Src-transformed 3T3 xenograft model in vivo, resulting in more than 90% growth inhibition at doses as low as 6 mg/kg po once daily. Src tyrosine kinase inhibitors such as these may provide a novel therapeutic modality for targeting cancer invasion and metastasis.

Quinazoline derivatives

The invention concerns quinazoline derivatives of Formula (I) wherein Q1includes a quinazoline ring optionally substituted with a group such as halogeno, trifluoromethyl and cyano, or a group of the formula: Q3—X1— wherein X1includes a direct bond and O and Q3includes aryl, aryl-(1-6C)alkyl, heterocyclyl and heterocyclyl-(1-6C)alkyl; each of R2and R3is hydrogen or (1-6C)alkyl; Z includes O, S and NH; and Q2includes aryl and aryl-(1-3C)alkyl or a pharmaceutically-acceptable salt thereof; processes for their preparation, pharmaceutical compositions containing them and their use in the manufacture of a medicament for use in the prevention or treatment of T cell mediated diseases or medical conditions in a warm-blooded animal.