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CERPEGIN, a naturally occurring pyridinone alkaloid, is derived from Roxb, a traditional Indian medicine. It is characterized by its beige solid appearance and is known for its tranquilizing, anti-inflammatory, analgesic, and antiulcer properties.

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  • 145887-88-3 Structure
  • Basic information

    1. Product Name: CERPEGIN
    2. Synonyms: CERPEGIN;1,1-Dimethylfuro[3,4-C]pyridine-3,4(1H,5H)-dione
    3. CAS NO:145887-88-3
    4. Molecular Formula: C9H9NO3
    5. Molecular Weight: 179.17266
    6. EINECS: N/A
    7. Product Categories: Bases & Related Reagents;Nucleotides;Aromatics;Heterocycles;Intermediates & Fine Chemicals;Pharmaceuticals;Aromatics, Heterocycles, Pharmaceuticals, Intermediates & Fine Chemicals
    8. Mol File: 145887-88-3.mol
  • Chemical Properties

    1. Melting Point: 257-260℃ (ligroine )
    2. Boiling Point: 535.1°C at 760 mmHg
    3. Flash Point: 277.4°C
    4. Appearance: Beige Solid
    5. Density: 1.32±0.1 g/cm3 (20 oC 760 Torr), Calc.
    6. Vapor Pressure: 1.59E-11mmHg at 25°C
    7. Refractive Index: 1.574
    8. Storage Temp.: N/A
    9. Solubility: N/A
    10. PKA: 10.51±0.40(Predicted)
    11. CAS DataBase Reference: CERPEGIN(CAS DataBase Reference)
    12. NIST Chemistry Reference: CERPEGIN(145887-88-3)
    13. EPA Substance Registry System: CERPEGIN(145887-88-3)
  • 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: 145887-88-3(Hazardous Substances Data)

145887-88-3 Usage

Uses

Used in Pharmaceutical Industry:
CERPEGIN is used as a tranquilizer for its calming effects on the central nervous system, helping to alleviate anxiety and stress.
CERPEGIN is used as an anti-inflammatory agent to reduce inflammation and swelling, making it useful in treating various inflammatory conditions.
CERPEGIN is used as an analgesic to relieve pain, providing an alternative to conventional pain-relieving medications.
CERPEGIN is used as an antiulcer agent to protect and heal the lining of the stomach and intestines, helping to treat and prevent ulcers.

Check Digit Verification of cas no

The CAS Registry Mumber 145887-88-3 includes 9 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 6 digits, 1,4,5,8,8 and 7 respectively; the second part has 2 digits, 8 and 8 respectively.
Calculate Digit Verification of CAS Registry Number 145887-88:
(8*1)+(7*4)+(6*5)+(5*8)+(4*8)+(3*7)+(2*8)+(1*8)=183
183 % 10 = 3
So 145887-88-3 is a valid CAS Registry Number.
InChI:InChI=1/C9H9NO3/c1-9(2)5-3-4-10-7(11)6(5)8(12)13-9/h3-4H,1-2H3,(H,10,11)

145887-88-3SDS

SAFETY DATA SHEETS

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

Version: 1.0

Creation Date: Aug 17, 2017

Revision Date: Aug 17, 2017

1.Identification

1.1 GHS Product identifier

Product name 1,1-dimethyl-5H-furo[3,4-c]pyridine-3,4-dione

1.2 Other means of identification

Product number -
Other names 1,1-dimethylfuro<3,4-c>pyridine-3,4(1H,5H)-dione

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:145887-88-3 SDS

145887-88-3Relevant articles and documents

A new series of N5 derivatives of the 1,1,5-trimethyl furo[3,4-c]pyridine-3,4-dione (cerpegin) selectively inhibits the post-acid activity of mammalian 20S proteasomes

Pham, The Hien,Hovhannisyan, Anna,Bouvier, Dominique,Tian, Lei,Reboud-Ravaux, Michèle,Melikyan, Gagik,Bouvier-Durand, Michelle

, p. 3822 - 3827 (2012)

A large set of N5-derivatives of cerpegin (1,1,5-trimethyl furo[3,4-c]pyridine-3,4-dione) was designed and synthesized in high yields by a simple and handy method using various primary amines for a pyridine cycle synthesis. The effects of 29 derivatives on the three types of catalytic sites of purified mammalian 20S proteasomes (CT-L, T-L and PA) were measured. Most of the new compounds specifically inhibited the PA activity, in the micromolar range. Docking experiments support these results. Moreover, neither calpain I nor cathepsin B were inhibited.

Cerpegin-derived furo[3,4-c]pyridine-3,4(1H,5H)-diones enhance cellular response to interferons by de novo pyrimidine biosynthesis inhibition

Alves de Sousa, Rodolphe,Arnould, Stéphanie,Bekaddour, Nassima,Dairou, Julien,Diaz, Olivier,Ermellino, Laura,Hayek, Simon,Herbeuval, Jean-Philippe,Hovhannisyan, Anna A.,Lotteau, Vincent,Melikyan, Gagik,Nisole, Sébastien,Pietrancosta, Nicolas,Sardet, Claude,Tramontano, Enzo,Vidalain, Pierre-Olivier

, (2019)

There is an increasing interest in the field of cancer therapy for small compounds targeting pyrimidine biosynthesis, and in particular dihydroorotate dehydrogenase (DHODH), the fourth enzyme of this metabolic pathway. Three available DHODH structures, fe

New C4- and C1-derivatives of furo[3,4-c]pyridine-3- ones and related compounds: Evidence for site-specific inhibition of the constitutive proteasome and its immunoisoform

Hovhannisyan, Anna,Pham, The Hien,Bouvier, Dominique,Piroyan, Alexander,Dufau, Laure,Qin, Lixian,Cheng, Yan,Melikyan, Gagik,Reboud-Ravaux, Michèle,Bouvier-Durand, Michelle

supporting information, p. 1571 - 1580 (2014/03/21)

A set of 18 new C4 and C1 derivatives of nor-cerpegin (1,1-dimethyl furo[3,4-c]pyridine-3-one), 6 model compounds (γ- and δ-lactones) and 20 furo- or thieno[2,3-d]-pyrimidine-4-one related compounds were designed and synthesized. Each compound was assayed for inhibition of CT-L, T-L and PA proteolytic activities of 20S constitutive proteasome (c20S). Most performant compounds were also assayed on 20S immunoproteasome (i20S). Compound 10 with a benzylamino group at C4 and dimethylated at C1 of the furopyridine ring was the most efficient PA site-specific inhibitor of the c20S (IC50cPA of 600 nM) without noticeable inhibition of the i20S PA site (iPA). In silico docking assays for 10 at the iPA catalytic site revealed the absence of poses normally observed for this compound and related ones at the constitutive PA site (cPA). The thieno[2,3-d]pyrimidine-4-one 40 was T-L site-specific with a mild inhibition of both c20S and i20S in vitro (IC50cT-L of 9.9 μM and IC50iT-L of 6.7 μM). In silico docking assays of 40 at T-L sites of c20S and i20S revealed almost identical first rank poses in the two types of sites with no possibility left for nucleophilic attack by Thr1 as observed for the fused furopyridine-3-one 10.

Two versatile routes towards Cerpegin and analogues: Applications of a one pot reaction to new analogues of Cerpegin

Villemin, Didier,Cheikh, Nawel,Liao, Liang,Bar, Nathalie,Lohier, Jean-Fran?ois,Sopkova, Jana,Choukchou-Braham, Noureddine,Mostefa-Kara, Bachir

experimental part, p. 4906 - 4918 (2012/07/28)

Simple and efficient routes to the natural alkaloid Cerpegin and new analogues are described herein. In a first approach, we extend the scope of a one pot three steps reaction, which permits the synthesis of new analogues of Cerpegin, substituted in different ways. In a second line of approach, we present an unprecedented synthesis of Cerpegin and analogues where methylfuranones are condensed with dimethylformamide diethylacetal (DMFDEA) to yield enaminolactone esters, which react easily with various primary amines affording Cerpegin and new analogues. We applied this second approach to the synthesis of new bis-Cerpegins and N-amino-Cerpegins. Most of the syntheses are performed under environmental friendly conditions.

'One-pot' four-step synthesis of cerpegin

Lazaar, Jalal,Hoarau, Christophe,Mongin, Florence,Trécourt, Francois,Godard, Alain,Quéguiner, Guy,Marsais, Francis

, p. 3811 - 3813 (2007/10/03)

Cerpegin (1) was synthesized through a 'one-pot' reaction in 71% overall yield. Lithiation of commercially available 2-methoxynicotinic acid (2) as its lithium salt using LTMP, followed by addition of acetone at low temperature and a specific acidic treatment of the intermediate 3 thus obtained, gave the 1,1-dimethyl-3,4-dioxo-1,3,4,5-tetrahydrofuro[3,4-c]pyridine (4). The latter was finally selectively alkylated using methyl iodide and caesium carbonate to afford cerpegin (1).

One-pot three steps synthesis of cerpegin

Villemin, Didier,Liao, Liang

, p. 8733 - 8734 (2007/10/03)

Cerpegin 1 was synthesized in a one-pot reaction at room temperature catalysed by cesium carbonate with an overall of 75% yield. 3-Hydroxy-3-methyl-2-butanone 2 reacted with diethyl malonate 3 to give 2-ethoxycarbonyl-3,4,4-trimethyl-2-buten-4-olide 4. Then 4 with s-triazine gave to 1,1-dimethylfuro[3,4-c]pyridine-3,4(1H, 5H)-dione 5 and which was alkylated with methyliodide to cerpegin.

Metalation of pi-deficient heterocycles a facile synthesis of cerpegin

Guillier, Fabricee,Nivoliers, Francois,Bourguignon, Jean,Dupas, Georges,Marsais, Francis,Godard, Alain,Queguiner, Guy

, p. 7355 - 7356 (2007/10/02)

The first total synthesis of the naturally occuring cerpegin is described. Metalation of a pyridine derivative has been used in the key step.

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