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Ethyl 7-methoxy-4-oxo-1,4-dihydroquinoline-3-carboxylate is a complex ester chemical compound characterized by the presence of an ethyl group, a 4-oxo-1,4-dihydroquinoline ring, and a carboxylate group. The incorporation of a methoxy group at the 7th position of the quinoline ring contributes to its unique chemical properties. As a quinoline derivative, it may exhibit a range of biological activities, making it a promising candidate for pharmaceutical applications.

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  • 71083-05-1 Structure
  • Basic information

    1. Product Name: ethyl 7-methoxy-4-oxo-1,4-dihydroquinoline-3-carboxylate
    2. Synonyms: ethyl 7-methoxy-4-oxo-1,4-dihydroquinoline-3-carboxylate
    3. CAS NO:71083-05-1
    4. Molecular Formula: C13H13NO4
    5. Molecular Weight: 247.24662
    6. EINECS: N/A
    7. Product Categories: N/A
    8. Mol File: 71083-05-1.mol
  • Chemical Properties

    1. Melting Point: N/A
    2. Boiling Point: N/A
    3. Flash Point: N/A
    4. Appearance: /
    5. Density: N/A
    6. Refractive Index: N/A
    7. Storage Temp.: N/A
    8. Solubility: N/A
    9. CAS DataBase Reference: ethyl 7-methoxy-4-oxo-1,4-dihydroquinoline-3-carboxylate(CAS DataBase Reference)
    10. NIST Chemistry Reference: ethyl 7-methoxy-4-oxo-1,4-dihydroquinoline-3-carboxylate(71083-05-1)
    11. EPA Substance Registry System: ethyl 7-methoxy-4-oxo-1,4-dihydroquinoline-3-carboxylate(71083-05-1)
  • Safety Data

    1. Hazard Codes: N/A
    2. Statements: N/A
    3. Safety Statements: N/A
    4. WGK Germany:
    5. RTECS:
    6. HazardClass: N/A
    7. PackingGroup: N/A
    8. Hazardous Substances Data: 71083-05-1(Hazardous Substances Data)

71083-05-1 Usage

Uses

Used in Pharmaceutical Industry:
Ethyl 7-methoxy-4-oxo-1,4-dihydroquinoline-3-carboxylate is used as a potential pharmaceutical agent for its diverse biological activities. The presence of the quinoline ring structure is known to confer properties such as antimicrobial, anticancer, antimalarial, and anti-inflammatory effects. Its specific applications and efficacy in medicine would require further research and analysis to fully harness its potential.
Given the information provided, there are no specific applications detailed for different industries beyond the general mention of potential pharmaceutical uses. Further research would be necessary to identify and validate specific applications in various industries, such as in drug development for targeted therapies or as an intermediate in the synthesis of other bioactive compounds.

Check Digit Verification of cas no

The CAS Registry Mumber 71083-05-1 includes 8 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 5 digits, 7,1,0,8 and 3 respectively; the second part has 2 digits, 0 and 5 respectively.
Calculate Digit Verification of CAS Registry Number 71083-05:
(7*7)+(6*1)+(5*0)+(4*8)+(3*3)+(2*0)+(1*5)=101
101 % 10 = 1
So 71083-05-1 is a valid CAS Registry Number.

71083-05-1SDS

SAFETY DATA SHEETS

According to Globally Harmonized System of Classification and Labelling of Chemicals (GHS) - Sixth revised edition

Version: 1.0

Creation Date: Aug 18, 2017

Revision Date: Aug 18, 2017

1.Identification

1.1 GHS Product identifier

Product name Ethyl 7-methoxy-4-oxo-1,4-dihydro-3-quinolinecarboxylate

1.2 Other means of identification

Product number -
Other names 1H-Indole-2-carboxylic acid,7-methoxy-,ethyl ester

1.3 Recommended use of the chemical and restrictions on use

Identified uses For industry use only.
Uses advised against no data available

1.4 Supplier's details

1.5 Emergency phone number

Emergency phone number -
Service hours Monday to Friday, 9am-5pm (Standard time zone: UTC/GMT +8 hours).

More Details:71083-05-1 SDS

71083-05-1Relevant articles and documents

3-(Benzo[: D] thiazol-2-yl)-4-aminoquinoline derivatives as novel scaffold topoisomerase i inhibitor via DNA intercalation: Design, synthesis, and antitumor activities

Chen, Nan-Ying,Gu, Zi-Yu,Li, Xiao-Juan,Liao, Hao-Ran,Mo, Dong-Liang,Pan, Cheng-Xue,Su, Gui-Fa,Yuan, Jing-Mei,Zhang, Guo-Hai

, p. 11203 - 11214 (2020/07/15)

Twenty-seven 3-(benzo[d]thiazol-2-yl)-4-aminoquinoline derivatives have been designed and synthesized as topoisomerase I inhibitors. The in vitro anti-proliferation evaluation against four human cancer cell lines (MGC-803, HepG-2, T24, and NCI-H460) and one normal cell line (HL-7702) indicated that most of them exhibited potent cytotoxicity. Among them, 5a was identified as the most promising candidate with a low IC50 value of about 2.20 ± 0.14 and was selected for further exploration. Spectroscopic analyses and agarose-gel electrophoresis assays indicated that 5a could interact with DNA and strongly inhibit topoisomerase I (Topo I). Further screening of the Topo I activity of compounds 5b, 5c, 5e, 5f, 5h, 5i, 5j, 5l, and 5n suggested that some of the compounds might exert quite a different cytotoxicity profile to that of 5a. Molecular modeling studies confirmed that 5a adopts a unique mode to interact with DNA and Topo I. Other molecular mechanistic studies suggested that the treatment of MGC-803 cells with 5a induces S phase arrest, up-regulates the pro-apoptotic protein, down-regulates the anti-apoptotic protein, activates caspase-3, and subsequently induces mitochondrial dysfunction so as to induce cell apoptosis. The in vivo efficiency of 5a was also evaluated on MGC-803 xenograft nude mice and the relative tumor growth inhibition was 42.4percent at 12 mg kg-1 without an obvious loss in the body weight. This journal is

Design, synthesis, structure-activity relationships and mechanism of action of new quinoline derivatives as potential antitumor agents

Li, Shangze,Hu, Lihua,Li, Jianru,Zhu, Jiongchang,Zeng, Feng,Huang, Qiuhua,Qiu, Liqin,Du, Runlei,Cao, Rihui

, p. 666 - 678 (2018/11/30)

A series of new quinoline derivatives was designed, synthesized and evaluated as potential antitumor agents. The results indicated that most compounds exhibited potent antiproliferative activity, and 7-(4-fluorobenzyloxy)–N-(2-(dimethylamino)- ethyl)quinolin-4-amine 10g was found to be the most potent antiproliferative agent against human tumor cell lines with an IC50 value of less than 1.0 μM. Preliminary structure-activity relationships analysis suggested that (1) the large and bulky alkoxy substituent in position-7 might be a beneficial pharmacophoric group for antiproliferative activity; (2) the amino side chain substituents in position-4 facilitated the antiproliferative activity of this class of compounds; and (3) the length of the alkylamino side chain moiety affected the antiproliferative potency, with two CH2 units being the most favorable. Further investigation of the mechanism of action of this class of compounds demonstrated that the representative compound 10g triggered p53/Bax-dependent colorectal cancer cell apoptosis by activating p53 transcriptional activity. Moreover, the results showed that compound 10g effectively inhibited tumor growth in a colorectal cancer xenograft model in nude mice. Thus, these quinoline derivatives might serve as candidates for the development of new antitumor drugs.

Design, synthesis and biological evaluation of new quinoline derivatives as potential antitumor agents

Su, Tong,Zhu, Jiongchang,Sun, Rongqin,Zhang, Huihui,Huang, Qiuhua,Zhang, Xiaodong,Du, Runlei,Qiu, Liqin,Cao, Rihui

, p. 154 - 167 (2019/06/11)

A series of new quinoline derivatives was designed, synthesized and evaluated for their antiproliferative activity. The results demonstrated that compounds 11p, 11s, 11v, 11x and 11y exhibited potent antiproliferative activity with IC50 value of lower than 10 μM against seven human tumor cell lines, and N-(3-methoxyphenyl)-7- (3-phenylpropoxy)quinolin-4-amine 11x was found to be the most potent antiproliferative agent against HCT-116, RKO, A2780 and Hela cell lines with an IC50 value of 2.56, 3.67, 3.46 and 2.71 μM, respectively. The antitumor efficacy of the representative compound 11x in mice was also evaluated, and the results showed that compound 11x effectively inhibited tumor growth and decreased tumor weight in animal models. Further investigation on mechanism of action indicated that compound 11x could inhibit colorectal cancer growth through ATG5-depenent autophagy pathway. Therefore, these quinoline derivatives are a new class of molecules that have the potential to be developed as new antitumor drugs.

Structural development of a type-1 ryanodine receptor (RyR1) Ca2+-release channel inhibitor guided by endoplasmic reticulum Ca2+ assay

Mori, Shuichi,Iinuma, Hiroto,Manaka, Noriaki,Ishigami-Yuasa, Mari,Murayama, Takashi,Nishijima, Yoshiaki,Sakurai, Akiko,Arai, Ryota,Kurebayashi, Nagomi,Sakurai, Takashi,Kagechika, Hiroyuki

, p. 837 - 848 (2019/07/12)

Type-1 ryanodine receptor (RyR1) is a calcium-release channel localized on sarcoplasmic reticulum (SR) of the skeletal muscle, and mediates muscle contraction by releasing Ca2+ from the SR. Genetic mutations of RyR1 are associated with skeletal muscle diseases such as malignant hyperthermia and central core diseases, in which over-activation of RyR1 causes leakage of Ca2+ from the SR. We recently developed an efficient high-throughput screening system based on the measurement of Ca2+ in endoplasmic reticulum, and used it to identify oxolinic acid (1) as a novel RyR1 channel inhibitor. Here, we designed and synthesized a series of quinolone derivatives based on 1 as a lead compound. Derivatives bearing a long alkyl chain at the nitrogen atom of the quinolone ring and having a suitable substituent at the 7-position of quinolone exhibited potent RyR1 channel-inhibitory activity. Among the synthesized compounds, 14h showed more potent activity than dantrolene, a known RyR1 inhibitor, and exhibited high RyR1 selectivity over RyR2 and RyR3. These compounds may be promising leads for clinically applicable RyR1 channel inhibitors.

Green efficient synthesis method of quinolone compound

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Paragraph 0017; 0018, (2019/05/08)

The invention discloses a green efficient synthesis method of a quinolone compound. The method is as follows: Step 1, a dicarbonyl compound, triethyl orthoformate and an aniline compound react in theabsence of a solvent and a catalyst to obtain an enamine ester intermediate; and Step 2, the enamine ester intermediate is subjected to an intramolecular cyclization reaction under the action of a cyclization reagent diphenyl ether to obtain a quinolone parent ring compound. The purity of the product reaches up to 98.8%. the synthesis method of the invention has the following main beneficial effects: 1, the reaction in the Step 1 is efficient, and no catalyst or solvent is used so as to avoid generation of the three wastes and the yield is high; 2, the process in the step 2 is green, the cyclization reagent can be recycled and reused; and 3, the process is simple, the steps 1 and 2 can be carried out in the same reactor, and the quinolone compound is obtained after reaction and filtration.

Synthesis, structure-activity relationships and preliminary mechanism of action of novel water-soluble 4-quinolone-3-carboxamides as antiproliferative agents

Zhang, Zeyan,Xiao, Xingpeng,Su, Tong,Wu, Jinyi,Ren, Jianwei,Zhu, Jiongchang,Zhang, Xiaodong,Cao, Rihui,Du, Runlei

, p. 239 - 251 (2017/09/25)

A series of novel water-soluble 4-quinolone-3-carboxamides was prepared and evaluated as antiproliferative agents. Preliminary results indicated that most compounds tested in this study showed potent antiproliferative potencies against human tumor cell li

For antibacterial chlorine oxygen kui derivatives

-

Paragraph 0172-0173; 0177-0178; 0185-0186, (2017/08/29)

The invention relates to an oxo-quinoline derivative with activity of resisting bacterial infection relevant diseases such as helicobacter pylori (Hp) infection disease. The invention specifically relates to a compound as shown in formula I in the specification, and a pharmaceutically acceptable salt, solvate or prodrug thereof, wherein R is selected from hydrogen, -C alkyl, -C alkenyl, -C alkynyl, or -C alkyl-phenyl, and the alkyl, alkenyl, alkynyl and phenyl can be randomly substituted by halogen, nitro, cyan, hydroxyl, -C alkoxy and phenyl; R is selected from hydrogen, -CONHR and -COOR, R and R are independently selected from -C alkyl and -C alkyl amino, and the amino is randomly substituted by one to two -C alkyls; R is selected from halogen, -C alkoxy, morpholinyl or piperazinyl.

With anti-tumor activity of chlorine oxygen kui derivatives

-

Paragraph 0176; 0180; 0181; 0188; 0189, (2017/12/28)

The invention relates to a chloroxoquinoline derivatives with anti-tumor activity and specifically relates to compounds of a formula I as shown in the specification and pharmaceutically acceptable salts, solvates and prodrugs thereof, wherein R1 is selected from hydrogen, -C1-6 alkyl, -C2-6 alkenyl, -C2-6 alkynyl and -C1-6 alkyl-phenyl, and the alkyl, the alkenyl, the alkynyl and the phenyl can be optionally substituted by halogens, nitryl, cyan, hydroxyl, -C1-6 alkoxy and phenyl; R3 is selected from hydrogen, -CONHR31 and -COOR32, the R31 and the R32 are independently selected from -C1-6 alkyl and -C1-6 alkylamino, respectively, and the amino can be optionally substituted by 1 to 2 -C1-6 alkyls; R7 is selected from halogens, -C1-6 alkoxy, morpholinyl and piperazine; the formula I is as shown in the specification.

Further studies on bis-charged tetraazacyclophanes as potent inhibitors of small conductance Ca2+-activated K+ channels

Yang, Donglai,Arifhodzic, Lejla,Ganellin, C. Robin,Jenkinson, Donald H.

, p. 907 - 923 (2013/07/27)

Previously, quinolinium-based tetraazacyclophanes, such as UCL 1684 and UCL 1848, have been shown to be extraordinarily sensitive to changes in chemical structure (especially to the size of the cyclophane system) with respect to activity as potent non-peptidic blockers of the small conductance Ca 2+-activated K+ ion channels (SKCa). The present work has sought to optimize the structure of the linking chains in UCL 1848. We report the synthesis and SKCa channel-blocking activity of 29 analogues of UCL 1848 in which the central CH2 of UCL 1848 is replaced by other groups X or Y = O, S, CF2, CO, CHOH, CC, CHCH, CHMe to explore whether subtle changes in bond length or flexibility can improve potency still further. The possibility of improving potency by introducing ring substituents has also been explored by synthesizing and testing 25 analogues of UCL 1684 and UCL 1848 with substituents (NO2, NH2, CF 3, F, Cl, CH3, OCH3, OCF3, OH) in the 5, 6 or 7 positions of the aminoquinolinium rings. As in our earlier work, each compound was assayed for inhibition of the afterhyperpolarization (AHP) in rat sympathetic neurons, an action mediated by the SK3 subtype of the SK Ca channel. One of the new compounds (39, R7 = Cl, UCL 2053) is twice as potent as UCL 1848 and UCL 1684: seven are comparable in activity.

Molecular design, synthesis and biological evaluation of 1,4-dihydro-4-oxoquinoline ribonucleosides as TcGAPDH inhibitors with trypanocidal activity

Soares, Fabyana A.,Sesti-Costa, Renata,Da Silva, Jo?o Santana,De Souza, Maria Cecília B.V.,Ferreira, Vitor F.,Da C. Santos, Fernanda,Monteiro, Patricia A.U.,Leit?o, Andrei,Montanari, Carlos A.

, p. 4597 - 4601 (2013/08/15)

The 1,4-dihydro-4-oxoquinoline ribonucleoside, Neq135, is the first low micromolar trypanosomatidae inhibitor to show good ligand efficiency (0.28 kcal mol-1 atom-1) and good ligand lipophilicity efficiency (0.37 kcal mol-1/sup

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