406192-81-2

Usage

Uses

Used in Pharmaceutical Industry:
1-Isoquinolinecarboxylicacid,hydrazide(9CI) is used as an intermediate in the synthesis of various pharmaceutical compounds for its antitubercular properties.
Used in Antitubercular Medications:
1-Isoquinolinecarboxylicacid,hydrazide(9CI) is used as a key component in the development of isoniazid, a medication used for the treatment of tuberculosis. Isoniazid works by inhibiting the synthesis of mycolic acids in the cell wall of the tuberculosis bacteria, leading to the bactericidal effect. It is considered an essential part of the first-line treatment for tuberculosis and is often used in combination with other medications to combat the disease effectively.

Upstream product

• 16675-59-5 methyl isoquinoline-5-carboxylate 
• 27810-64-6 isoquinoline-5-carboxylic acid 
• 50458-78-1 ethyl isoquinoline-1-carboxylate 
• 486-73-7 1-isoquinolinecarboxylic acid 
• 21233-61-4 quinoline-4-carboxylic acid methyl ester 
• 4363-93-3 quinoline-4-carboxaldehyde 
• 27104-72-9 methyl isoquinoline-1-carboxylate 

Relevant academic research and scientific papers

A chromone hydrazide Schiff base fluorescence probe with high selectivity and sensitivity for the detection and discrimination of human serum albumin (HSA) and bovine serum albumin (BSA)

The discrimination and identification of human serum albumin (HSA) and bovine serum albumin (BSA) is very important, which is due to the vital roles of two SAs in biological and pharmaceutical research. Based on structural screening and docking calculation from a series of homologues, a coumarin Schiff base fluorescent probe 3-hydroxy-N′-((4-oxo-4H-chromen-3-yl)methylene)-2-naphthohydrazide (HCNH) has been designed and synthesized, which could effectively discriminate HSA and BSA. The probe HCNH exhibited superior sensitivity toward HSA and BSA with the detection limits of 10.62 nM and 16.03 nM in PBS solution, respectively. The binding mechanism of HCNH with SAs was studied by Job's plot analysis, SA destruction and displacement assay. Molecular docking and DFT methods were utilized to provide deep insight into the spatial conformation change of HCNH and binding sites in HSA/BSA. The conformation of HCNH was significantly influenced by the microenvironment provided by HSA and BSA, therefore its fluorescence emission was affected correspondingly. Non-toxic probe HCNH could be successfully used for fluorescence bio-imaging of HSA in cancer cells, which is significantly different from normal cells and favors the application in medical diagnosis.

Aluminum ion detection fluorescent probe based on bifunctional organic small molecule as matrix and preparation method and application thereof

The invention discloses an aluminum ion detection fluorescent probe based on a bifunctional organic small molecule as a matrix and a preparation method and application of the fluorescence probe, and the structural formula is shown I. To the invention, 1, 8 - naphthalimide and isoquinoline hydrazide or 2 - benzamide benzoyl hydrazine are used as fluorescent groups, and the prepared Schiff base type probe NIQ or NBP is prepared into a solution Al through condensation reaction. 3 + High sensitivity and high selectivity are exhibited, and at the same time, the structure is stable. The low toxicity and cell infiltration capability is strong, and the trace metal aluminum ions in the living Hela cells are successfully detected. The preparation method of the fluorescent probe is simple, the raw materials are easily available, the obtained product is solid powder, is easy to store, and has a high application development prospect.

Microscale Parallel Synthesis of Acylated Aminotriazoles Enabling the Development of Factor XIIa and Thrombin Inhibitors

Herein we report a microscale parallel synthetic approach allowing for rapid access to libraries of N-acylated aminotriazoles and screening of their inhibitory activity against factor XIIa (FXIIa) and thrombin, which are targets for antithrombotic drugs. This approach, in combination with post-screening structure optimization, yielded a potent 7 nM inhibitor of FXIIa and a 25 nM thrombin inhibitor; both compounds showed no inhibition of the other tested serine proteases. Selected N-acylated aminotriazoles exhibited anticoagulant properties in vitro influencing the intrinsic blood coagulation pathway, but not extrinsic coagulation. Mechanistic studies of FXIIa inhibition suggested that synthesized N-acylated aminotriazoles are covalent inhibitors of FXIIa. These synthesized compounds may serve as a promising starting point for the development of novel antithrombotic drugs.

Fluorescence “On-Off” chemical sensor for ultrasensitive detection of Al3+ in live cell

An efficient fluorescent probe, 3, 3-bis(4-hydroxyphenyl)-2-benzofuran-1-one-isoquinoline-1-carbohydrazide hydrazine (L), has been prepared for the selective sensing of Al3+ in DMSO-H2O (90:10, v/v) solution. The 1:2 stoichiometry of

A dual-functional fluorescent probe for sequential determination of Cu2+/S2? and its applications in biological systems

A new acylhydrazine-derived Schiff base fluorescence probe DMI based on “ON-OFF-ON” fluorescence strategy was presented in this paper. Probe DMI could detect Cu2+ selectively and sensitively with dramatic fluorescence quenching in CH3OH-PBS (v/v = 3:7) mixed solution. Once the complex DMI-Cu2+ interacted with S2?, 10.67-folds fluorescence increase was induced via a displacement mechanism under the same experimental conditions. The corresponding detection limits for Cu2+ and S2? were calculated to be 1.52 × 10?8 M and 1.79 × 10?8 M, respectively. The structures of DMI and DMI-Cu2+ were systematically characterized by Job's plot analysis, ESI-MS, IR, X-ray diffraction and density functional theory calculations. Furthermore, fluorescence imaging in MCF-7 cells and zebrafish demonstrated the probe DMI could act as a useful tool to monitor and track intracellular Cu2+ and S2?, which was encouraged by remarkable fluorescence performance and low cytotoxicity. Importantly, the complex DMI-Cu2+ could be applied to detect corrupt blood samples, which could estimate the time of death.

Phenolphthalein Schiff base fluorescent probe and preparation method and application thereof

The invention discloses a phenolphthalein Schiff base fluorescent probe and a preparation method and application thereof, and relates to the field of fluorescent molecular probes. The phenolphthaleinSchiff base fluorescent probe is used for identifying Al

Synthesis, leishmanicidal, trypanocidal and cytotoxic activity of quinoline-hydrazone hybrids

Abstract Cutaneous leishmaniasis and Chagas disease are vector-borne parasitic disease causing serious risks to million people living in poverty-stricken areas. Both diseases are a major health problem in Latin America, and currently drugs for the effective treatment of these diseases have important concerns related with efficacy or toxicity than need to be addressed.We report herein the synthesis and biological activities (cytotoxicity, leishmanicidal and trypanocidal activities) of ten quinolone-hydrazone hybrids. The structure of the products was elucidated by spectrometric analyses. The synthesized compounds were evaluated against amastigotes forms of L. (V) panamensis which is the most prevalent Leishmania species in Colombia and Trypanosoma cruzi that is the major pathogenic species to humans; in turn, cytotoxicity was evaluated against human U-937 macrophages.Compounds 6b, 6c and 8 showed activity against L. (V) panamensis with EC50 of 6.5 ± 0.8 μg/mL (21.2 μM), 0.8 ± 0.0 μg/mL (2.6 μM) and 3.4 ± 0.6 μg/mL (11.1 μM), respectively, while compounds 6a and 6c had activity against T. cruzi. with EC50 values of 1.4 ± 0.3 μg/mL (4.8 μM) and 6.6 ± 0.3 μg/mL (4.6 μM), respectively. Even compound 6a showed better activity against T. cruzi than the standard drug benznidazole with EC50 Combining double low line 10.5 ± 1.8 μg/mL (40.3 μM).Analysis of the results obtained against leishmaniasis indicates that antiparasite activity is related to the presence of 2-substituted quinoline (isoquinolinic core) and the hydroxyl group in positions 3 and 4 of the aromatic ring. Although the majority of these compounds were highly cytotoxic, the antiparasite activity was higher than cytotoxicity and therefore, they still have potential to be considered as hit molecules for leishmanicidal and trypanocidal drug development.

Dual-action inhibitors of HIF prolyl hydroxylases that induce binding of a second iron ion

Inhibition of the hypoxia-inducible factor (HIF) prolyl hydroxylases (PHD or EGLN enzymes) is of interest for the treatment of anemia and ischemia-related diseases. Most PHD inhibitors work by binding to the single ferrous ion and competing with 2-oxoglutarate (2OG) co-substrate for binding at the PHD active site. Non-specific iron chelators also inhibit the PHDs, both in vitro and in cells. We report the identification of dual action PHD inhibitors, which bind to the active site iron and also induce the binding of a second iron ion at the active site. Following analysis of small-molecule iron complexes and application of non-denaturing protein mass spectrometry to assess PHD2·iron· inhibitor stoichiometry, selected diacylhydrazines were identified as PHD2 inhibitors that induce the binding of a second iron ion. Some compounds were shown to inhibit the HIF hydroxylases in human hepatoma and renal carcinoma cell lines. The Royal Society of Chemistry 2013.