218451-34-4

Basic information

• Product Name: TERT-BUTYL 4-(4-CHLOROPHENYL)-4-CYANOPIPERIDINE-1-CARBOXYLATE
• Synonyms: TERT-BUTYL 4-(4-CHLOROPHENYL)-4-CYANOPIPERIDINE-1-CARBOXYLATE;1-Boc-4-cyano-4-(4-chlorophenyl)-piperidine
• CAS NO: 218451-34-4
• Molecular Formula: C₁₇H₂₁ClN₂O₂
• Molecular Weight: 320.81
• Mol File: 218451-34-4.mol

Chemical Properties

• Appearance: /
• Storage Temp.: 2-8°C
• CAS DataBase Reference: TERT-BUTYL 4-(4-CHLOROPHENYL)-4-CYANOPIPERIDINE-1-CARBOXYLATE(CAS DataBase Reference)
• NIST Chemistry Reference: TERT-BUTYL 4-(4-CHLOROPHENYL)-4-CYANOPIPERIDINE-1-CARBOXYLATE(218451-34-4)
• EPA Substance Registry System: TERT-BUTYL 4-(4-CHLOROPHENYL)-4-CYANOPIPERIDINE-1-CARBOXYLATE(218451-34-4)

Safety Data

• Hazardous Substances Data: 218451-34-4(Hazardous Substances Data)

Upstream product

• 623-03-0 4-Cyanochlorobenzene 
• 118753-70-1 N-(tert-butyloxycarbonyl)bis(2-chloroethyl)amine 
• 24424-99-5 di-tert-butyl dicarbonate 
• 140-53-4 p-chlorobenzyl cyanide 

Downstream Products

• 917925-59-8 tert-butyl 4-amino-4-(4-chlorophenyl)piperidine-1-carboxylate 
• 887129-04-6 4-(4-chloro-phenyl)-piperidine-1,4-dicarboxylic acid mono-(9H-fluoren-9-ylmethyl) ester 
• 885500-56-1 4-[4-(4-chlorophenyl)-4-(1,3-dioxo-1,3-dihydroisoindol-2-ylmethyl)-piperidin-1-yl]-1H-pyrrolo[2,3-b]pyridine-5-carboxylic acid ethyl ester 
• 885500-57-2 4-[4-(4-chlorophenyl)-4-(1,3-dioxo-1,3-dihydroisoindol-2-ylmethyl)-piperidin-1-yl]-1H-pyrrolo[2,3-b]pyridine-5-carboxylic acid 
• 885500-71-0 2-[4-(4-chlorophenyl)-piperidin-4-ylmethyl]-isoindole-1,3-dione 
• 885500-47-0 4-(4-chloro-phenyl)-4-methylaminomethyl-piperidine-1-carboxylic acid tert-butyl ester 
• 1092790-63-0 C₂₇H₂₃ClN₄O₂ 
• 885653-41-8 C-(4-(4-chlorophenyl)piperidin-4-yl)methylamine 

Relevant articles and documents

Design, synthesis and biological evaluation of AKT inhibitors bearing a piperidin-4-yl appendant

A series of AKT inhibitors possessing a piperidin-4-yl side chain was designed and synthesized. Some of them showed high AKT1 inhibitory activity and potent anti-proliferative effect on PC-3 prostate cancer cells in the preliminary screening. Further studies revealed the most potent compound, 10h, as a pan-AKT inhibitor. Compound 10h was able to inhibit the cellular phosphorylation of AKT effectively and induce apoptosis of PC-3 cells. It also showed high metabolic stability in human liver microsomes. Preclinical characterization of 10h, a promising lead AKT inhibitor, as a potential anti-prostate cancer therapeutic needs to be further investigated.

Substituted p-chlorophenyl acetylpiperazine-containing compound as well as preparation method and application thereof

The application provides a substituted p-chlorophenyl acetylpiperazine-containing compound as well as a preparation method and application of the substituted p-chlorophenyl acetylpiperazine-containingcompound. The compound has the structure shown in the formula (I), and has better Akt1 inhibitory activity or growth inhibitory activity to MCL cell lines.

A nitrogen-containing heterocyclic phenyl piperidine compound and its preparation method and application

The invention discloses a nitrogen-containing heterocyclic phenyl piperidine compound or pharmaceutical salt thereof. The general structural formula a of the compound is as shown in specification, wherein R represents hydrogen, mono-substituted or poly-substituted halogen, methyl, methoxyl, tertiary butyl or trifluoromethyl; and R2 is hydrogen, chlorine, bromine, methyl or ethyl. The compound disclosed by the invention is novel in structure; and by introducing the active amino in the form of a piperidine ring, the configuration of the side-chain amino is reinforced and the rigidity of the compound is enhanced. Through the design transformation, the Akt1 kinase inhibitory activity and the PC-3 cell line growth inhibitory activity of the compound are significantly enhanced.

Structural optimization elaborates novel potent Akt inhibitors with promising anticancer activity

Targeting of Akt has been validated as a well rationalized approach to cancer treatment, and represents a promising therapeutic strategy for aggressive hematologic malignancies. We describe herein an exploration of novel Akt inhibitors for cancer therapy through structural optimization of previously described 4-(piperazin-1-yl)-7H-pyrrolo[2,3-d]pyrimidine derivatives. Our studies yielded a novel series of pyrrolopyrimidine based phenylpiperidine carboxamides capable of potent inhibition of Akt1. Notably, 10h exhibited robust antiproliferative effects in both mantle cell lymphoma cell lines and primary patient tumor cells. Low micromolar doses of 10h induced cell apoptosis and cell cycle arrest in G2/M phase, and significantly downregulated the phosphorylation of Akt downstream effectors GSK3β and S6 in Jeko-1 cells.

TRIAZOLOPYRIDINE COMPOUNDS AND METHODS OF USE THEREOF

Provided are triazolopyridine compounds that are inhibitors of JAK kinase, such as JAK1, compositions containing these compounds and methods for treating diseases mediated by a JAK kinase. In particular, provided are compounds of formula (I), stereoisomer

CHEMOKINE RECEPTOR ANTAGONISTS AND METHODS OF USE THEREOF

Disclosed are novel compounds and a method of treating a disease associated with aberrant leukocyte recruitment and/or activation. The method comprises administering to a subject in need an effective amount of a compound represented by: or physiologically acceptable salt thereof.

TRIAZOLOPYRIDINE COMPOUNDS, COMPOSITIONS AND METHODS OF USE THEREOF

Compounds of Formula 0, Formula I and Formula II and methods of use as Janus kinase inhibitors are described herein.

CHEMOKING RECEPTOR ANTAGONISTS

Disclosed herein are chemokine receptor antagonists of formula (I) wherein G1, X1, X2, and X3 are as defined in the specification. Compositions comprising such compounds; and methods for treating conditions and disorders using such compounds and compositions are also described.

Identification of 4-(4-aminopiperidin-1-yl)-7H-pyrrolo[2,3-d]pyrimidines as selective inhibitors of protein kinase B through fragment elaboration

Fragment-based screening identified 7-azaindole as a protein kinase B inhibitor scaffold. Fragment elaboration using iterative crystallography of inhibitor-PKA-PKB chimera complexes efficiently guided improvements in the potency and selectivity of the compounds, resulting in the identification of nanomolar 6-(piperidin-1-yl)purine, 4-(piperidin-1-yl)-7-azaindole, and 4-(piperidin-1-yl)pyrrolo[2,3-d]pyrimidine inhibitors of PKBβ with antiproliferative activity and showing pathway inhibition in cells. A divergence in the binding mode was seen between 4-aminomethylpiperidine and 4-aminopiperidine containing molecules. Selectivity for PKB vs PKA was observed with 4-aminopiperidine derivatives, and the most PKB-selective inhibitor (30-fold) showed significantly different bound conformations between PKA and PKA-PKB chimera.

PHARMACEUTICAL COMPOUNDS

The invention provides a compound of the formula (I) or salts, solvates, tautomers or N-oxides thereof, wherein T is N or CR5; J1-J2 is N=C(R6), (R7)C=N, (R8)N-C(O), (R8)2C-C(O), N=N or (R7)C=C(R6); E is a monocyclic carbocyclic or heterocyclic group of 5 or 6 ring members, the heterocyclic group containing up to 3 heteroatoms selected from O, N and S; Q1 is a bond or a saturated C1-3 hydrocarbon linker group, one of the carbon atoms in the linker group being optionally be replaced by an oxygen or nitrogen atom, or an adjacent pair of carbon atoms may be replaced by CONRq or NRqCO where Rq is hydrogen or methyl, or Rq is a C1-4 alkylene chain linked to R1 or a carbon atom of Q1 to form a cyclic moiety; and wherein the carbon atoms of the linker group Q1 may optionally bear one or more substituents selected from fluorine and hydroxy; Q2 is a bond or a saturated hydrocarbon linker group containing from 1 to 3 carbon atoms, wherein one of the carbon atoms in the linker group may optionally be replaced by an oxygen or nitrogen atom; and wherein the carbon atoms of the linker group may optionally bear one or more substituents selected from fluorine and hydroxy, provided that the hydroxy group when present is not located at a carbon atom α with respect to the G group; and provided that when E is aryl or heteroaryl, then Q2 is other than a bond; G is hydrogen, NR2R3, OH or SH provided that when E is aryl or heteroaryl and Q2 is a bond, then G is hydrogen; R1 is hydrogen or an aryl or heteroaryl group, with the proviso that when R1 is hydrogen and G is NR2R3, then Q2 is a bond; and R2, R3, R4, R6 and R8 are as defined in the claims, wherein the compound is for use in: (a) the treatment or prophylaxis of a disease or condition in which the modulation (e.g. inhibition) of ROCK kinase or protein kinase P70S6K is indicated; and/or (b) the treatment of a subject or patient population in which the modulation (e.g. inhibition) of ROCK kinase or protein kinase P70S6K is indicated.