27913-98-0

Usage

Uses

Used in Pharmaceutical Industry:
4-PIPERAZIN-1-YL-BENZALDEHYDE is used as a potential therapeutic agent for its antitumor properties, targeting various types of cancer. Its antimalarial and antiviral activities also position it as a candidate for the development of treatments against infectious diseases.
Used in Drug Discovery:
In the field of drug discovery, 4-PIPERAZIN-1-YL-BENZALDEHYDE is utilized as a lead compound for the development of new medications. Its diverse biological activities make it a valuable starting point for designing drugs that can address multiple health concerns.
Used in Medicinal Chemistry Research:
4-PIPERAZIN-1-YL-BENZALDEHYDE serves as a subject of interest in medicinal chemistry research, where its structure and properties are studied to understand its mechanisms of action and to optimize its therapeutic potential.
While the provided materials do not specify different applications in various industries, the general uses listed above encompass the potential applications of 4-PIPERAZIN-1-YL-BENZALDEHYDE based on its described properties and the context of its study in medicinal chemistry.

Synthetic route

piperazine (110-85-0) + 4-fluorobenzaldehyde (459-57-4) → 4-(piperazin-1-yl) benzaldehyde (27913-98-0)

Conditions	Yield
In 2-methoxy-ethanol; water for 3h; Heating;	68%
In 2-methoxy-ethanol; water for 3h; Reflux;	65.9%
In 2-methoxy-ethanol for 3h; Reflux;	65%

4-(4-(1,1-dimethylethoxycarbonyl)piperazinyl)benzaldehyde (197638-83-8) → 4-(piperazin-1-yl) benzaldehyde (27913-98-0)

Conditions	Yield
With trifluoroacetic acid In dichloromethane at 20℃; for 1.5h;

4-(piperazin-1-yl) benzaldehyde (27913-98-0) + 9-amino-3,4-dihydro-1H-pyrido[4,3-e][1,4]diazepin-5(2H)-one → 1-(4-(piperazin-1-yl)phenyl)-8,9-dihydro-2,4,7,9a-tetraazabenzo[cd]azulen-6(7H)-one

Conditions	Yield
With palladium 10% on activated carbon In methanol at 120℃; for 24h; Sealed tube;	92.6%

4-(piperazin-1-yl) benzaldehyde (27913-98-0) + di-tert-butyl dicarbonate (24424-99-5) → 4-(4-(1,1-dimethylethoxycarbonyl)piperazinyl)benzaldehyde (197638-83-8)

Conditions	Yield
In tetrahydrofuran; dichloromethane at 20℃; for 16h; Inert atmosphere;	92%

4-(piperazin-1-yl) benzaldehyde (27913-98-0) + 3-dicyanomethylidene-1,5,5-trimethylcyclohexene (23051-44-7) → (E)-2-(5,5-dimethyl-3-(4-(piperazin-1-yl)styryl)cyclohex-2-en-1-ylidene)malononitrile

Conditions	Yield
In ethanol Concentration; Reflux;	87%

4-(piperazin-1-yl) benzaldehyde (27913-98-0) + p-toluenesulfonyl chloride (98-59-9) → C18H20N2O3S

Conditions	Yield
With triethylamine In dichloromethane at 20 - 30℃; Inert atmosphere;	83.1%

4-(piperazin-1-yl) benzaldehyde (27913-98-0) + 4-(3-Hydroxy-4-oxo-4H-chromen-2-yl)benzoic acid → 4-(4-(4-(3-hydroxy-4-oxo-4H-chromen-2-yl)benzoyl)piperazin-1-yl)benzaldehyde

Conditions	Yield
With dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In dichloromethane at 20℃; for 8h;	82%
With dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In dichloromethane at 20℃; for 0.8h;	128 mg

4-(piperazin-1-yl) benzaldehyde (27913-98-0) + 6-bromo-2-(2-morpholinoethyl)-1H-benzo[de]isoquinoline1,3 (2 H)-dione (182344-68-9) → C29H30N4O4

Conditions	Yield
In 2-methoxy-ethanol at 80℃; for 8h;	72%

4-(piperazin-1-yl) benzaldehyde (27913-98-0) + 4,6-dichloro-2-methylquinoline (53342-53-3) → C21H19Cl2N3

Conditions	Yield
With toluene-4-sulfonamide In toluene at 120℃; for 12h;	72%

4-(piperazin-1-yl) benzaldehyde (27913-98-0) + 4-chloro-2-methylquinoline (4295-06-1) → C21H20ClN3

Conditions	Yield
With toluene-4-sulfonamide In toluene at 120℃; for 12h;	71%

4-(piperazin-1-yl) benzaldehyde (27913-98-0) + benzyl chloroformate (501-53-1) → benzyl 4-(4-formylphenyl)piperazine-1-carboxylate (104055-50-7)

Conditions	Yield
With N-ethyl-N,N-diisopropylamine In dichloromethane at 20℃; Inert atmosphere;	70%

4-(piperazin-1-yl) benzaldehyde (27913-98-0) + 4-(dicyanomethylene)-2-isopropyl-6-methyl-4H-pyran (263902-75-6) → 2-{2-[4-(piperazin-1-yl)styryl]-6-isopropyl-4H-pyran-4-ylidene}malonodinitrile (950583-83-2)

Conditions	Yield
With piperidine; acetic acid In acetonitrile for 8h; Heating;	65%

4-(piperazin-1-yl) benzaldehyde (27913-98-0) + 2,3-diamino-6-fluorobenzamide → C23H26FN5O3

Conditions	Yield
With sodium hydrogen sulfite In methanol for 12h; Reflux;	64%

4-(piperazin-1-yl) benzaldehyde (27913-98-0) + 4-bromo-N-butylnaphthalimide (92874-17-4) → C27H27N3O3

Conditions	Yield
In N,N-dimethyl-formamide for 6h; Reflux; Inert atmosphere;	62%

4-(piperazin-1-yl) benzaldehyde (27913-98-0) + C27H29ClN4O2 (923950-47-4) → C38H42N6O3

Conditions	Yield
In acetonitrile for 6h; Reflux;	61%

4-(piperazin-1-yl) benzaldehyde (27913-98-0) + 3-dicyanomethylidene-1,5,5-trimethylcyclohexene (23051-44-7) → -2-(5,5-dimethyl-3-(4-(piperazin-1-yl)styryl)cyclohex-2-en-1-ylidene) malononitrile

Conditions	Yield
With piperidine In ethanol for 5h; Inert atmosphere; Reflux;	61%
With piperidine In ethanol for 5h; Inert atmosphere; Reflux;	61%
With piperidine; acetic acid In toluene for 8h; Reflux;	42%

4-(piperazin-1-yl) benzaldehyde (27913-98-0) + N2,N6-bis(1-hydrazinyl-2-methyl-1-oxopropan-2-yl)pyridine-2,6-dicarboxamide (1233515-62-2) → N2,N6-bis(N-(1-{(2E)-2-[4-(piperazin-1-yl)benzylidene]hydrazinyl}-2-methyl-1-oxo-propan-2-yl))pyridine-2,6-dicarboxamide

Conditions	Yield
With acetic acid Reflux;	57%

4-(piperazin-1-yl) benzaldehyde (27913-98-0) + 1,3,5-trichloro-2,4,6-triazine (108-77-0) → C25H26ClN7O2

Conditions	Yield
With caesium carbonate In chloroform at 20℃; for 16h;	56%

4-(piperazin-1-yl) benzaldehyde (27913-98-0) + C11H12NO4(1-)*K(1+) → C21H25N3O3

Conditions	Yield
With manganese(IV) oxide; copper(l) iodide; zinc diacetate In N,N-dimethyl-formamide at 30℃; for 45h; Inert atmosphere; Sealed tube; chemoselective reaction;	53%

4-(piperazin-1-yl) benzaldehyde (27913-98-0) + 4-methoxy-6-methyl-2H-pyran-2-one (672-89-9) → (E)-4-methoxy-6-(4-(piperazin-1-yl)styryl)-2H-pyran-2-one

Conditions	Yield
With magnesium methanolate In methanol for 20h; Reflux; Inert atmosphere;	20%

4-(piperazin-1-yl) benzaldehyde (27913-98-0) + C33H37N4O3(1+) → C44H49N6O3(1+)

Conditions	Yield
With potassium iodide In ethanol for 12h; Inert atmosphere; Reflux;	15%

piperidine (110-89-4) + 4-(piperazin-1-yl) benzaldehyde (27913-98-0) + 2-oxoindole (59-48-3) → 3-[4-(4-Formylpiperazin-1-yl)benzylidenyl]-2-indolinone

Conditions	Yield
In ethanol	199.5 mg (65%)

4-(piperazin-1-yl) benzaldehyde (27913-98-0) + 2,4-dichloro-5-bromopyrimidine (36082-50-5) → C15H16Cl2N4O (1259179-50-4)

Conditions	Yield
Stage #1: 2,4-dichloro-5-bromopyrimidine With isopropylmagnesium chloride In tetrahydrofuran at -78 - -40℃; Inert atmosphere; Stage #2: 4-(piperazin-1-yl) benzaldehyde In tetrahydrofuran at -40 - 0℃; Inert atmosphere; Stage #3: With water; ammonium chloride In tetrahydrofuran Inert atmosphere;

4-(piperazin-1-yl) benzaldehyde (27913-98-0) → 1-(4-(4-(6-bromo-7-(4-((5-methylisoxazol-3-yl)methyl)piperazin-1-yl)-3H-imidazo[4,5-b]pyridin-2-yl)phenyl)piperazin-1-yl)ethanone (1402709-63-0)

Conditions	Yield
Multi-step reaction with 2 steps 1: N-ethyl-N,N-diisopropylamine / dichloromethane / 4 h / 20 °C / Inert atmosphere 2: sodium dithionite / ethanol; water / 20 h / 80 °C View Scheme

4-(piperazin-1-yl) benzaldehyde (27913-98-0) + acetyl chloride (75-36-5) → 4-(4-acetylpiperazin-1-yl)benzaldehyde (890092-19-0)

Conditions	Yield
With N-ethyl-N,N-diisopropylamine In dichloromethane at 20℃; for 4h; Inert atmosphere;	0.052 g

4-(piperazin-1-yl) benzaldehyde (27913-98-0) + 4-Chloro-2-(pyridin-2-yl)-quinazoline (91748-47-9) → 1-(4-{4-[2-(pyridin-2-yl)quinazolin-4-yl]piperazin-1-yl}phenyl)methanone (1431939-93-3)

Conditions	Yield
With N-ethyl-N,N-diisopropylamine In 1,4-dioxane at 110℃;

4-(piperazin-1-yl) benzaldehyde (27913-98-0) + C16H11N3OS → C27H23N5OS

Conditions	Yield
With piperidine In ethanol at 80℃; for 16h;	25 mg

4-(piperazin-1-yl) benzaldehyde (27913-98-0) + C17H12N2OS (924200-99-7) → C28H24N4OS

Conditions	Yield
With piperidine In ethanol at 80℃; for 16h;	26 mg

4-(piperazin-1-yl) benzaldehyde (27913-98-0) + 7-azaoxindole (5654-97-7) → C18H18N4O

Conditions	Yield
With sodium ethanolate In ethanol at 20℃;

4-(piperazin-1-yl) benzaldehyde (27913-98-0) → C20H19N3O2

Conditions	Yield
Multi-step reaction with 2 steps 1: sodium ethanolate / ethanol / 20 °C 2: 50 °C View Scheme

Upstream product

• 110-85-0 piperazine 
• 459-57-4 4-fluorobenzaldehyde 
• 197638-83-8 4-(4-(1,1-dimethylethoxycarbonyl)piperazinyl)benzaldehyde 

Downstream Products

• 950583-83-2 2-{2-[4-(piperazin-1-yl)styryl]-6-isopropyl-4H-pyran-4-ylidene}malonodinitrile 

Relevant academic research and scientific papers

Ultrasensitive dicyanoisophorone-based near-infrared fluorescent probe for rapid and specific detection of thiophenols in river water

Thiophenols are a class of highly toxic pollutant compounds, which can cause severe damage to the central nervous system and other nervous systems after long-term exposure. Therefore, it is of significance to develop an effective method to detect trace thiophenols in the environment. Herein, we synthesized a dicyanoisophorone-based near-infrared fluorescent probe (probe 1) with large stokes shift (λem ? λabs = 203?nm) for the selective detection of thiophenols. Probe 1 exhibited very high response speed (less than 200 S), sensitivity, and selectivity towards thiophenols, regardless of the presence of aliphatic thiols and other analytes. The detection limit was as low as 3.4?nM and the signal-to-background ratio of fluorescence intensity reached 30. Moreover, probe 1 displayed ultrasensitivity and high reliability in the quantitative detection of trace thiophenol in three river water samples.

A mitochondria-targeted fluorescent probe for ratiometric detection of endogenous sulfur dioxide derivatives in cancer cells

A new mitochondria-targeted fluorescent probe HCy-D, constructed by dansyl and hemicyanine fluorophores, for SO2 derivatives (HSO3-/SO32-) was presented. This probe was designed based on a new FRET platform. HCy-D showed a ratiometric, sensitive and rapid response to HSO3-/SO32-. Importantly, HCy-D was successfully used for fluorescence imaging of endogenous bisulfite in HepG2 cells, which may benefit cancer diagnosis by discriminating liver cancer cells from normal liver cells.

A ratiometric and colorimetric fluorescent probe designed based on FRET for detecting SO32?/HSO3? in living cells and mice

Based on the principle of FRET, we have developed a ratiometric and colorimetric fluorescent probe TFBN, which can specifically recognize SO2 derivatives (SO32?/HSO3?), and exhibit a transition from red to green fluorescence under 405 nm excitation. The probe TFBN owns the advantages of short response time (2 derivatives in two linear ranges, extremely low detection limit (39 nM), large Stokes shift (239 nm) and wide emission window gap (140 nm). In addition, the NBC structure was used as a fluorescent donor for FRET probes for the first time, which expanded the diversity of donors. Importantly, with low toxicity and good biocompatibility, the probe TFBN successfully detects exogenous and endogenous sulfites in living cells. These characteristics endow the probe TFBN can be successfully used in living cells and mouse imaging.

Fluorescent probe for near infrared detection of cysteine as well as preparation method and application of fluorescent probe

The invention provides a fluorescent probe with the advantages of reduced background interference, high sample penetration performance, good selectivity, high sensitivity and good imaging resolution for fluorescence open-close type near infrared detection of cysteine as well as a preparation method and application of the fluorescent probe. The fluorescent probe is subjected to fluorescence quenching by taking near infrared fluorescent parent nucleus containing a plurality of double bonds as a fluorophore and taking 2,4-dinitrobenzene sulfonamide as a quenching unit; in actual detection, in thepresence of the cysteine, sulfydryl of the cysteine carries out nucleophilic substitution reaction on electron deficient aromatic ring, a sulfonamide bond cracks and a fluorescence quencher is dissociated, so that the fluorescent probe without fluorescence or with weak fluorescence based on intramolecular charge transfer (ICT) process releases the fluorescent parent nucleus, fluorescence is enhanced or opened to generate a fluorescent signal for selectively recognizing the cysteine, and further the aims of selective recognition and analysis and detection of the cysteine (Cys) are achieved.

Aromatic-ring azacyclo derivatives and application thereof

Aromatic-ring azacyclo derivatives and an application thereof are provided. The invention relates to compounds represented by the formula (V), and a preparation method and an application thereof in medicines. In particular, the invention relates to derivatives of the compounds represented by the general formula (V), and a preparation method and the application thereof as therapeutic agents in prevention and treatment of hyperlipidemia, hypercholesterolemia, hypertriglyceridemia, hepatic steatosis, type-II diabetes, hyperglycemia, obesity or insulin resistance syndromes and metabolic syndromes. The compounds disclosed by the invention also can reduce total cholesterol, LDL-cholesterol and triglycerides, increase the expression of hepatic LDL receptors and inhibit the expression of PCSK9.

Synthesis and biological evaluation of novel oxindole-based RTK inhibitors as anti-cancer agents

Given that receptor tyrosine kinases (RTKs) have emerged as key regulators of all aspects of cancer development, including proliferation, invasion, angiogenesis and metastasis, the RTK family represents an important therapeutic target for anti-cancer drug development. Oxindole structure has been used in RTK inhibitors such as SU4984 and intedanib. In this study, two series of new heterocyclic compounds containing oxindole scaffold have been designed and synthesized, and their inhibitory activity against the proliferation of nine cancer cell lines has been evaluated. Among them, compounds 9a and 9b displayed the strongest anti-proliferative activity with the IC50s below 10 μM. Flow cytometric analysis showed that the compounds 9a and 9b dose-dependently arrested the cell cycle at G0/G1 phase. Although the leading compounds SU4984 and intedanib targets FGFR1, the kinase activity test revealed that these compounds only showed slight inhibitory activity on FGFR1 kinase. Further enzymatic test aided by molecular docking simulation in the ATP-binding site demonstrated that 9a and 9b are potent inhibitors of c-Kit kinase. These compounds are worthy of further evaluation as anticancer agents.

Optimization of imidazo[4,5- b ]pyridine-based kinase inhibitors: Identification of a dual FLT3/aurora kinase inhibitor as an orally bioavailable preclinical development candidate for the treatment of acute myeloid leukemia

Optimization of the imidazo[4,5-b]pyridine-based series of Aurora kinase inhibitors led to the identification of 6-chloro-7-(4-(4-chlorobenzyl)piperazin- 1-yl)-2-(1,3-dimethyl-1H-pyrazol-4-yl)-3H-imidazo[4,5-b]pyridine (27e), a potent inhibitor of Aurora kinases (Aurora-A Kd = 7.5 nM, Aurora-B K d = 48 nM), FLT3 kinase (Kd = 6.2 nM), and FLT3 mutants including FLT3-ITD (Kd = 38 nM) and FLT3(D835Y) (Kd = 14 nM). FLT3-ITD causes constitutive FLT3 kinase activation and is detected in 20-35% of adults and 15% of children with acute myeloid leukemia (AML), conferring a poor prognosis in both age groups. In an in vivo setting, 27e strongly inhibited the growth of a FLT3-ITD-positive AML human tumor xenograft (MV4-11) following oral administration, with in vivo biomarker modulation and plasma free drug exposures consistent with dual FLT3 and Aurora kinase inhibition. Compound 27e, an orally bioavailable dual FLT3 and Aurora kinase inhibitor, was selected as a preclinical development candidate for the treatment of human malignancies, in particular AML, in adults and children.

A fluorophore capable of crossword puzzles and logic memory

(Chemical Equation Presented) Puzzlingly logical: The characteristic fluorescence of Hg2+-selective OFF-ON and Cu2+-selective ON-OFF operations can be monitored and controlled reversibly by the sequence and ratio of Hg2+ and Cu2+ inputs. These inputs have been used to construct a molecular keyboard that is capable of crossword puzzles and logic memory (see picture).