388121-83-3

Basic information

• Product Name: Piperazine, 1-(3-butynyl)-4-methyl- (9CI)
• Synonyms: Piperazine, 1-(3-butynyl)-4-methyl- (9CI);1-(but-3-yn-1-yl)-4-methylpiperazine
• CAS NO: 388121-83-3
• Molecular Formula: C₉H₁₆N₂
• Molecular Weight: 152.23674
• Product Categories: AMINETERTIARY
• Mol File: 388121-83-3.mol

Chemical Properties

• Appearance: /
• CAS DataBase Reference: Piperazine, 1-(3-butynyl)-4-methyl- (9CI)(CAS DataBase Reference)
• NIST Chemistry Reference: Piperazine, 1-(3-butynyl)-4-methyl- (9CI)(388121-83-3)
• EPA Substance Registry System: Piperazine, 1-(3-butynyl)-4-methyl- (9CI)(388121-83-3)

Safety Data

• Hazardous Substances Data: 388121-83-3(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
Piperazine, 1-(3-butynyl)-4-methyl(9CI) is used as a reactant for the preparation of alkynoylamino (arylamino)quinazolines or (arylamino)pyridopyrimidines. These compounds exhibit significant activities as irreversible inhibitors of erbB tyrosine kinases, such as erbB1, erbB2, and erbB4. Inhibition of these kinases is crucial for the development of targeted therapies against various types of cancer, as they play a critical role in cell proliferation, survival, and differentiation.
The use of Piperazine, 1-(3-butynyl)-4-methyl(9CI) in the synthesis of these inhibitors is driven by its ability to form stable and bioactive compounds with potential therapeutic applications. By targeting erbB tyrosine kinases, these inhibitors can help in the development of novel anticancer drugs that can effectively combat cancer cells and improve patient outcomes.

Upstream product

• 109-01-3 1-methyl-piperazine 
• 23418-85-1 3-butyn-1-yl p-toluenesulfonate 

Downstream Products

• 885482-95-1 4-[(2,4-dichloro-5-methoxyphenyl)amino]-6-methoxy-7-[4-(4-methylpiperazin-1-yl)but-1-ynyl]-3-quinolinecarbonitrile 
• 946489-95-8 4-[(2,4-dichloro-5-methoxyphenyl)amino]-6-methoxy-7-[(1E)-4-(4-methylpiperazin-1-yl)but-1-enyl]quinoline-3-carbonitrile 
• 1100794-09-9 1-(4-(5-chloro-2-(phenylthio)phenyl)but-3-ynyl)-4-methylpiperazine 
• 544707-25-7 1-methyl-4-[4-(4-(piperidin-1-ylmethyl)phenyl)but-3-ynyl]piperazine 

Relevant articles and documents

Diamine-based human histamine H3 receptor antagonists: (4-Aminobutyn-1-yl)benzylamines

A series of (4-aminobutyn-1-yl)benzylamines were prepared and the SAR around three key areas: (1) the amine attached to the butynyl linker (R3R4N-); (2) the benzylamine moiety (R1R2N-); and (3) the point of attachment of the benzylamine group (R1R2N- in the ortho, meta, or para positions) was examined. One compound, 4-[3-(4-piperidin-1-yl-but-1-ynyl)-benzyl]-morpholine (9s) was chosen for further profiling and found to be a selective histamine H3 antagonist with desirable drug-like properties. Ex vivo receptor occupancy studies established that 9s does occupy H3 binding sites in the brain of rats after oral administration. Subcutaneous doses of 9s (10 mg/kg) given during the natural sleep phase demonstrated robust wake-promoting effects.

ALKYNYL PYRROLOPYRIMIDINES AND RELATED ANALOGS AS HSP90-INHIBITORS

Alkynyl pyrrolo[2,3-d]pyrimidines and related analogs are described and demonstrated to have utility as Heat Shock Protein 90 (HSP90) inhibiting agents used in the treatment and prevention of various HSP90 mediated disorders. Methods of synthesis and use of such compounds are also described and claimed.

Tyrosine kinase inhibitors. 19. 6-alkynamides of 4-anilinoquinazolines and 4-anilinopyrido[3,4-d]pyrimidines as irreversible inhibitors of the erbB family of tyrosine kinase receptors

Structure-activity relationships for inhibition of erbB1, erbB2, and erbB4 were determined for a series of alkynamide analogues of quinazoline- and pyrido[3,4-ui]pyrimidine-based compounds. The compounds were prepared by coupling the appropriate 6-aminoquinazolines or 6-aminopyrido[3,4-d]pyrimidines with alkynoic acids, using EDCI·HCl in pyridine. The compounds showed pan-erbB enzyme inhibition but were on average about 10-fold more potent against erbB1 than against erbB2 and erbB4. For cellular inhibition, the nature of the alkylating side chains was an important determinant, with 5-dialkylamino-2- pentynamide type Michael acceptors providing the highest potency. This is suggested to be due to an improved ability of the amine to participate in an autocatalysis of the Michael reaction with enzyme cysteine residues. Pyrido[3,4-d]pyrimidine analogue 39 was selected for in vivo evaluation and achieved tumor regressions at 10 mg/kg in the A431 human epidermoid carcinoma and at 40 mg/kg for the SF767 human glioblastoma and the SKOV3 human ovarian carcinoma. Complete stasis was observed at 40 mg/kg in the BXPC3 human pancreatic carcinoma as well as in the H125 human non-small-cell lung carcinoma.

Syntheses of [14C] and [2H4]PD0205520, an inhibitor of the tyrosine kinase activity of the epidermal growth factor receptor

5-(4-Methyl-piperazin-1-yl)-pent-2-ynoic acid [4-(3-chloro-4-fluoro- phenylamino)-pyrido[3,4-d]pyrimidin-6-yl]-amide, PD0205520, was under investigation as a potential inhibitor of the tyrosine kinase (TK) activity of the epidermal growth factor receptor (EGFR) for cancer treatment. Both radio- and stable-isotope-labeled compounds were required for drug absorption, distribution, metabolism and excretion (ADME) and quantitative mass spectrometry bio-analytical studies. PD0205520 14C-labeled in the pyrimidine ring system was prepared in seven steps in an overall radiochemical yield of 26% from [14C]thiourea. PD0205520 2H-labeled in the piperazine ring was synthesized in four steps in a 32% overall yield. Copyright