188527-21-1

Basic information

• Product Name: 1-N-CBZ-PYRROLIDINE-3-CARBOXYLIC ACID
• Synonyms: 1-N-CBZ-BETA-PROLINE;1-N-CBZ-PYRROLIDINE-3-CARBOXYLIC ACID;3-CARBOXY-1-CBZ-PYRROLIDINE;PYRROLIDINE-1,3-DICARBOXYLIC ACID 1-BENZYL ESTER;N-CBZ-PYRROLIDINE-3-CARBOXYLIC ACID;1-Cbz-3-pyrrolidinecarboxylic acid;1-Cbz-pyrrolidine-3-carboxylic acid;C67154
• CAS NO: 188527-21-1
• Molecular Formula: C₁₃H₁₅NO₄
• Molecular Weight: 249.26
• Product Categories: pharmacetical
• Mol File: 188527-21-1.mol

Chemical Properties

• Boiling Point: 432.3°Cat760mmHg
• Flash Point: 215.3°C
• Appearance: /Solid
• Density: 1.309g/cm³
• Vapor Pressure: 3.06E-08mmHg at 25°C
• Refractive Index: 1.582
• Storage Temp.: under inert gas (nitrogen or Argon) at 2-8°C
• PKA: 4.46±0.20(Predicted)
• CAS DataBase Reference: 1-N-CBZ-PYRROLIDINE-3-CARBOXYLIC ACID(CAS DataBase Reference)
• NIST Chemistry Reference: 1-N-CBZ-PYRROLIDINE-3-CARBOXYLIC ACID(188527-21-1)
• EPA Substance Registry System: 1-N-CBZ-PYRROLIDINE-3-CARBOXYLIC ACID(188527-21-1)

Safety Data

• Hazard Codes: Xi
• Statements: 43
• Safety Statements: 36/37
• Hazardous Substances Data: 188527-21-1(Hazardous Substances Data)

Usage

Uses

1-?(Benzyloxycarbonyl)?pyrrolidine-?3-?carboxylic Acid is a reagent used in the synthesis of cyclin-dependent kinase 4-inhibitors (CDK4) for cancer treatments. Also used towards the discovery of a potent inhibitor of poly(ADP-ribose) polymerase (PARP) for the treatment of cancer pased upon benzimidazole carboxamide moieties.

InChI:InChI=1/C13H15NO4/c15-12(16)11-6-7-14(8-11)13(17)18-9-10-4-2-1-3-5-10/h1-5,11H,6-9H2,(H,15,16)

Upstream product

• 5731-18-0 1-benzyl-pyrrolidine-3-carboxylic acid 
• 501-53-1 benzyl chloroformate 
• 188847-00-9 pyrrolidine-1,3-dicarboxylic acid 1-benzyl ester 3-methyl ester 

Downstream Products

• 874217-97-7 (R/S)-4-[(1-Benzyloxycarbonyl-pyrrolidine-3-carbonyl)-amino]-piperidine-1-carboxylic acid tert-butyl ester 

Relevant articles and documents

Discovery of the PARP (poly ADP-ribose polymerase) inhibitor 2-(1-(4,4-difluorocyclohexyl)piperidin-4-yl)-1H-benzo[d]imidazole-4-carboxamide for the treatment of cancer

In this work, two series of cyclic amine-containing benzimidazole carboxamide derivatives were designed and synthesized as potent anticancer agents. PARP1/2 inhibitory activity assays indicated that most of the compounds showed significant activity. The in vitro antiproliferative activity of these compounds was investigated against four human cancer cell lines (MDA-MB-436, MDA-MB-231, MCF-7 and CAPAN-1), and several compounds exhibited strong cytotoxicity to tumor cells. Among them, 2-(1-(4,4-difluorocyclohexyl)piperidin-4-yl)-1H-benzo[d]imidazole-4-carboxamide (17d) was found to be effective PARP1/2 inhibitors (IC50 = 4.30 and 1.58 nM, respectively). In addition, 17d possessed obvious selective antineoplastic activity and noteworthy microsomal metabolic stability. What's more, further studies revealed that 17d was endowed with an excellent ADME profile. These combined results indicated that 17d could be a promising candidate for the treatment of cancer.

Discovery of 2-(1-(3-(4-Chloroxyphenyl)-3-oxo-propyl)pyrrolidine-3-yl)-1H-benzo[d]imidazole-4-carboxamide: A Potent Poly(ADP-ribose) Polymerase (PARP) Inhibitor for Treatment of Cancer

A series of benzimidazole carboxamide derivatives have been synthesized and characterized by 1H-NMR, 13C-NMR and HRMS. PARP inhibition assays and cellular proliferation assays have also been carried out. Compounds 5cj and 5cp exhibited potential anticancer activities with IC50 values of about 4 nM against both PARP-1 and PARP-2, similar to the reference drug veliparib. The two compounds also displayed slightly better in vitro cytotoxicities against MDA-MB-436 and CAPAN-1 cell lines than veliparib and olaparib, with values of 17.4 μM and 11.4 μM, 19.8 μM and 15.5 μM, respectively. The structure-activity relationship based on molecular docking was discussed as well.

With antifungal activity of the wicked zuozuo apperception compound and its preparation method and application (by machine translation)

The invention discloses an oxazole compound with anti-fungal activity, a preparation method of the oxazole compound and an application of the oxazole compound to tobacco powdery mildew original fungi or cotton anthracnose original fungi prevention, and belongs to the technical field of organic synthesis. The technical scheme mainly includes that the oxazole compound with the anti-fungal activity is provided with a structure shown in the instruction, R1 refers to propiono, isopropyl, acetyl, ethyl or methyl, and R2 refers to dimethylamino or methylamine. Five oxazole compounds with the anti-fungal activity are synthesized by the novel method, the preparation process is simple in technology and easy to control, target product yield is high, repeatability is fine, and the five prepared oxazole compounds with the anti-fungal activity have a certain prevention function for tobacco powdery mildew original fungi or cotton anthracnose original fungi.

Cyclic amine compounds as CCR5 antagonists

A compound of formula (I) (wherein R1is a hydrogen atom, a hydrocarbon group which may be substituted, a non-aromatic heterocyclic group which may be substituted, R2is a hydrocarbon group which may be substituted, a non-aromatic heterocyclic group which may be substituted, or R1and R2may combine to each other together with A to form a heterocyclic group which may be substituted; A is N or N+—R5.Y?(R5is a hydrocarbon group; Y?is a counter anion); R3is a cyclic hydrocarbon group which may be substituted or a heterocyclic group which may be substituted; n is 0 or 1; R4is a hydrogen atom, a hydrocarbon group which may be substituted, a heterocyclic group which may be substituted, an alkoxy group which may be substituted, an aryloxy group which may be substituted, or an amino group which may be substituted, E is a divalent aliphatic hydrocarbon group which may be substituted by group(s) other than oxo; G1is a bond, CO or SO2; G2is CO, SO2, NHCO, CONH or OCO; J is methine or a nitrogen atom; and each of Q and R is a bond or a divalent C1-3aliphatic hydrocarbon which may be substituted; provided that J is methine when G2is OCO, that one of Q and R is not a bond when the other is a bond and that each of Q and R is not substituted by oxo group(s) when G1is a bond) or a salt thereof has a potent CCR5 antagonistic activity and can be advantageously used for the treatment or prevention of infectious disease of various HIV in human (e.g. AIDS).

Use of oxido-squalene cyclase inhibitors to lower blood cholesterol

PCT No. PCT/GB96/01985 Sec. 371 Date Feb. 13, 1998 Sec. 102(e) Date Feb. 13, 1998 PCT Filed Aug. 14, 1996 PCT Pub. No. WO97/06802 PCT Pub. Date Feb. 27, 1997A compound of formula (I), or a pharmaceutically acceptable salt thereof, wherein G, T1, T2 and T3 are selected from CH and N; provided that T2 and T3 are not both CH; A is selected from a direct bond and (1-4C)alkylene; X is selected from oxy, thio, sulphinyl, sulphonyl, carbonyl, carbonylamino, N-di-(1-6C)alkylcarbonylamino, sulphonamido, methylene, (1-4C)alkylmethylene and di-(1-6C)alkylmethylene, and when T2 is CH, X may also be selected from aminosulphonyl and oxycarbonyl; and Q is selected from (5-7C)cycloalkyl, a heterocyclic moiety containing up to 4 heteroatoms selected from nitrogen, oxygen and sulphur, phenyl, naphthyl, phenyl(1-4C)alkyl and phenyl(2-6C)alkenyl; for the manufacture of a medicament for treating diseases or medical conditions in which an inhibition of oxido-squalene cyclase is desirable.

Substituted pyrimidine derivatives and their pharmaceutical use

PCT No. PCT/GB97/02029 Sec. 371 Date Feb. 12, 1999 Sec. 102(e) Date Feb. 12, 1999 PCT Filed Jul. 25, 1997 PCT Pub. No. WO98/06705 PCT Pub. Date Feb. 19, 1998This invention concerns heterocyclic derivatives which are useful in inhibiting oxido-squalene cyclase, processes for their preparation and pharmaceutical compositions containing them. The present invention is also concerned with heterocyclic derivatives capable of inhibiting cholesterol biosynthesis and hence in lowering cholesterol levels in blood plasma. The present invention also relates to methods of using such heterocyclic derivatives in diseases and medical conditions such as hypercholesterolemia and atherosclerosis.

Pyrrolidine derivatives

Pyrrolidine derivatives which have the formula SPC1 Wherein R and R1 each is hydrogen, --(CH2)6 COOH, --(CH2)6 COO-- lower alkyl, or --(CH2)6 COO benzyl and R2 is hydrogen, --CO--O--(CH2)5 CH3, --CO--NH--(CH2)5 CH3 --(CH2)7 CH3 or --CH=CH--CH(OH)--(CH2)4 --CH3, at least one of R and R1 is hydrogen and R1 and R2 are not both hydrogen, are new compounds which are useful as inhibitors of prostaglandin dehydrogenase and as potentiators of prostaglandin activity.