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2-methoxy-5-morpholinoaniline, an organic compound with the chemical formula C9H12N2O2, is characterized by the presence of a methoxy group, a morpholino group, and an aniline moiety. It is recognized for its unique structure and potential medicinal properties, making it a valuable building block in the development of new drug molecules.

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  • 383870-88-0 Structure
  • Basic information

    1. Product Name: 2-methoxy-5-morpholinoaniline
    2. Synonyms: 2-methoxy-5-morpholinoaniline;Benzenamine, 2-methoxy-5-(4-morpholinyl)-
    3. CAS NO:383870-88-0
    4. Molecular Formula: C11H16N2O2
    5. Molecular Weight: 208.25694
    6. EINECS: N/A
    7. Product Categories: N/A
    8. Mol File: 383870-88-0.mol
  • Chemical Properties

    1. Melting Point: N/A
    2. Boiling Point: 412.5±45.0 °C(Predicted)
    3. Flash Point: N/A
    4. Appearance: /
    5. Density: 1.163±0.06 g/cm3(Predicted)
    6. Refractive Index: N/A
    7. Storage Temp.: 2-8°C
    8. Solubility: N/A
    9. PKA: 5.96±0.40(Predicted)
    10. CAS DataBase Reference: 2-methoxy-5-morpholinoaniline(CAS DataBase Reference)
    11. NIST Chemistry Reference: 2-methoxy-5-morpholinoaniline(383870-88-0)
    12. EPA Substance Registry System: 2-methoxy-5-morpholinoaniline(383870-88-0)
  • 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: 383870-88-0(Hazardous Substances Data)

383870-88-0 Usage

Uses

Used in Pharmaceutical Industry:
2-methoxy-5-morpholinoaniline is utilized as an intermediate in the synthesis of various pharmaceutical drugs, contributing to the development of novel therapeutic agents.
Used in Medicinal Chemistry Research:
2-methoxy-5-morpholinoaniline is employed as a starting material for the exploration of its anti-inflammatory and anticancer properties, indicating its potential as a lead compound in the discovery of new medications for these conditions.

Check Digit Verification of cas no

The CAS Registry Mumber 383870-88-0 includes 9 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 6 digits, 3,8,3,8,7 and 0 respectively; the second part has 2 digits, 8 and 8 respectively.
Calculate Digit Verification of CAS Registry Number 383870-88:
(8*3)+(7*8)+(6*3)+(5*8)+(4*7)+(3*0)+(2*8)+(1*8)=190
190 % 10 = 0
So 383870-88-0 is a valid CAS Registry Number.

383870-88-0Relevant articles and documents

Design, synthesis and biological evaluation of Tozadenant analogues as adenosine A2A receptor ligands

Renk, Dana R.,Skraban, Marcel,Bier, Dirk,Schulze, Annette,Wabbals, Erika,Wedekind, Franziska,Neumaier, Felix,Neumaier, Bernd,Holschbach, Marcus

, (2021/02/09)

With the aim to obtain potent adenosine A2A receptor (A2AR) ligands, a series of eighteen derivatives of 4-hydroxy-N-(4-methoxy-7-morpholin-4-yl-1,3-benzo[d]thiazol-2-yl)-4-methylpiperidine-1-carboxamide (SYN-115, Tozadenant) were designed and synthesized. The target compounds were obtained by a chemical building block principle that involved reaction of the appropriate aminobenzothiazole phenyl carbamates with either commercially available or readily synthesized functionalized piperidines. Their affinity and subtype selectivity with regard to human adenosine A1-and A2A receptors were determined using radioligand binding assays. Ki values for human A2AR ranged from 2.4 to 38 nM, with more than 120-fold selectivity over A1 receptors for all evaluated compounds except 13k which had a Ki of 361 nM and 18-fold selectivity. The most potent fluorine-containing derivatives 13e, 13g and 13l exhibited Ki values of 4.9 nM, 3.6 nM and 2.8 nM for the human A2AR. Interestingly, the corresponding values for rat A2AR were found to be four to five times higher. Their binding to A2AR was further confirmed by radiolabeling with 18F and in vitro autoradiography in rat brain slices, which showed almost exclusive striatal binding and complete displacement by the A2AR antagonist ZM 241385. We conclude that these compounds represent potential candidates for the visualization of the A2A receptor and open pathways to novel therapeutic treatments of neurodegenerative disorders or cancer.

Fluorinated adenosine A2A receptor antagonists inspired by preladenant as potential cancer immunotherapeutics

Yuan, Gengyang,Jankins, Tanner C.,Patrick, Christopher G.,Philbrook, Phaethon,Sears, Olivia,Hatfield, Stephen,Sitkovsky, Michail,Vasdev, Neil,Liang, Steven H.,Ondrechen, Mary Jo,Pollastri, Michael P.,Jones, Graham B.

, (2018/10/20)

Antagonism of the adenosine A2A receptor on T cells blocks the hypoxia-adenosinergic pathway to promote tumor rejection. Using an in vivo immunoassay based on the Concanavalin A mouse model, a series of A2A antagonists were studied and identified preladenant as a potent lead compound for development.Molecular modeling was employed to assist drug design and subsequent synthesis of analogs and those of tozadenant, including fluorinated polyethylene glycol PEGylated derivatives. The efficacy of the analogs was evaluated using two in vitro functional bioassays, and compound 29, a fluorinated triethylene glycol derivative of preladenant, was confirmed as a potential immunotherapeutic agent.

Discovery of novel 5-fluoro-N2,N4-diphenylpyrimidine-2,4-diamines as potent inhibitors against CDK2 and CDK9

Gao, Jiadi,Fang, Cheng,Xiao, Zhiyan,Huang, Li,Chen, Chin-Ho,Wang, Li-Ting,Lee, Kuo-Hsiung

, p. 444 - 454 (2015/03/18)

Based on a 3D-QSAR pharmacophore derived from a diverse set of known cyclin-dependent kinase 9 (CDK9) inhibitors and a composite pharmacophore extracted from the complex structure of flavopiridol (FVP)-CDK9, thirty novel 5-fluoro-N2,N4-diphenylpyrimidine-2,4-diamine derivatives were designed and synthesized. Initial tests against four tumor cell lines with the sulforhodamine B (SRB) assay identified a series of potent compounds with GI50 values at a lower micromolar or submicromolar level. Most of the highly cytotoxic compounds exhibited potent inhibitory activities against both CDK2/cyclin E1 and CDK9/cyclin T1. Notably, inhibitions against the two enzymes were generally correlated well with the cytotoxicity of these compounds. Appreciable inhibition was also observed for selected compounds in the anti-HIV-1 assay. Docking studies on compounds 6d and 9g provided conducive clues to further structural optimization. This journal is

PYRIMIDINE INHIBITORS OF KINASE ACTIVITY

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Page/Page column 94, (2010/12/26)

The present invention relates to compounds of formula (I) or pharmaceutical acceptable salts or solvates thereof, wherein G1, R2, R3, R4, R5, n, p, q, Ar1, and Ar2 are defined in the description. The present invention relates also to methods of making said compounds, and compositions comprising said compounds which are useful for inhibiting kinases such as IGF-IR.

NOVEL COMPOUNDS 515

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Page/Page column 166, (2010/05/13)

There is provided novel pyrimidine derivatives of formula (I) or pharmaceutically acceptable salts thereof, processes for their preparation, pharmaceutical compositions containing them and their use in therapy

DIKETOPIPERAZINE DERIVATIVES AS P2X7 MODULATORS

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Page/Page column 84, (2010/11/17)

The invention provides a compound of formula (I) or a pharmaceutically acceptable salt thereof: (I) wherein: A represents an aryl, heteroaryl or heterocyclyl group; and any ring or ring system of said aryl or heteroaryl is optionally substituted with 1 to 3 substituents, which may be the same or different, selected from the group consisting of halogen, C1-6 alkyl, -CF3, - OCF3, cyano, C1-6 alkoxy, -NR10R11, -X-aryl, -X-heteroaryl and -X-heterocyclyl; R1, R2, R3, R4 and R5 independently represent hydrogen, fluorine, chlorine, -CF3, cyano or C1-6 alkyl, such that at least one of R1, R2, R3, R4 and R5 is other than hydrogen; R6, R7, R8, R9, R10 and R11 independently represent hydrogen or C1-6 alkyl; X represents a linker selected from a bond, -(CH2)n- and -O-(CH2)n-; and n represents an integer from 1 to 3. The compounds or salts modulate P2X7 receptor function and are capable of antagonizing the effects of ATP at the P2X7 receptor ("P2X7 receptor antagonists").

4-Hydroxy-4-methyl-piperidine-1-carboxylic acid (4-methoxy-7-morpholin-4-yl-benzothiazol-2-yl)-amide

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Page/Page column 7, (2008/06/13)

The present invention relates to the compound of formula which is 4-hydroxy-4-methyl-piperidine-1-carboxylic acid(4-methoxy-7-morpholin-4-yl-benzothiazol-2-yl)-amide, and to pharmaceutically acceptable acid addition salts thereof. It has been found that the compound is useful for the treatment or prevention of Alzheimer's disease, Parkinson's disease, Huntington's disease, neuroprotection, schizophrenia, anxiety, pain, respiration deficits, depression, ADHD (attention deficit hyper-activity disorder), drug addiction to amphetamines, cocaine, opioids, ethanol, nicotine, or cannabinoids, or for the treatment of asthma, allergic responses, hypoxia, ischemia, seizure, substance abuse, or for use as muscle relaxants, antipsychotics, antiepileptics, anticonvulsants and cardioprotective agents.

Cyclization process for substituted benzothiazole derivatives

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Page/Page column 6-7, (2008/06/13)

The present invention relates to a process for preparation of amino substituted benzothiazole derivatives of formula I wherein R1, R2 and R3 are independently from each other hydrogen, lower alkyl, lower alkoxy or halogen; R4 is hydrogen, lower alkyl, lower alkyloxy, halogen, or is a five or six membered non aromatic heterocyclyl group, unsubstituted or substituted by lower alkyl or an oxo-group, or is —NR5R6, wherein R5 and R5 are independently from each other hydrogen, lower alkyl, —C(O)-lower alkyl, —(CH2)nO-lower alkyl or benzyl, opionally substituted by lower alkyl, or is an five or six membered heteroaryl group; R1 and R2 or R2 and R3 may form together with the corresponding carbon atoms a ring containing —O—CH2—O— or —CH═CH—CH═CH—; R is hydrogen or —C(O)R′; R′ is a five or six membered non aromatic heterocyclyl group, five or six membered heteroaryl group or is aryl, which rings may be substituted by the groups, selected from lower alkyl, halogen-lower alkyl, lower alkoxy, cyano, nitro, —C(O)H, —C(O)OH or by pyrrolidin-1-yl-methyl; n is 1 to 4; or a pharmaceutically acceptable salt thereof, wherein the cyclization is carried out by the treatment of a compound of formula with sulphoxide/HBr/solvent to give the desired products of formula I for R is hydrogen (formula IA) or for R is —C(O)R′ (formula IB)

Benzothiazole derivatives with activity as adenosine receptor ligands

-

, (2008/06/13)

The present invention relates to substituted benzothiazole derivitives and to their pharmaceutically acceptable salts useful for the treatment of diseases related to the adenosine receptor.

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