1769-41-1

Basic information

• Product Name: glyoxylanilide,2-oxime
• Synonyms: 2-(hydroxyimino)-n-phenyl-acetamid;2-isonitrosoacetanilide;glyoxanilideoxime;glyoxylanilide,2-oxime;glyoxylanilide,oxime;isonitrosoacetanilide;N-Phenyl-2-(hydroxyimino)acetamide;N-Phenyl-α-isonitrosoacetamide
• CAS NO: 1769-41-1
• Molecular Formula: C₈H₈N₂O₂
• Molecular Weight: 164.16132
• EINECS: 217-190-8
• Mol File: 1769-41-1.mol

Chemical Properties

• Boiling Point: 291.62°C (rough estimate)
• Flash Point: °C
• Appearance: /
• Density: 1.2739 (rough estimate)
• Refractive Index: 1.6000 (estimate)
• CAS DataBase Reference: glyoxylanilide,2-oxime(CAS DataBase Reference)
• NIST Chemistry Reference: glyoxylanilide,2-oxime(1769-41-1)
• EPA Substance Registry System: glyoxylanilide,2-oxime(1769-41-1)

Safety Data

• Hazardous Substances Data: 1769-41-1(Hazardous Substances Data)

Usage

Uses

Used in Organic Synthesis:
Glyoxylanilide,2-oxime is utilized as a reagent in organic synthesis for the formation of hydrazones and oximes, which are important intermediates in the synthesis of various organic compounds.
Used in Coordination Chemistry:
In the field of coordination chemistry, glyoxylanilide,2-oxime serves as a ligand, forming complexes with transition metal ions. This application is significant for the development of new materials with specific properties and potential uses in various industries.
Used in Pharmaceutical Industry:
Glyoxylanilide,2-oxime may also be employed in the pharmaceutical industry as a building block for the development of new drugs, given its ability to form stable complexes with metal ions, which can be crucial for medicinal applications.
Used in Chemical Research:
glyoxylanilide,2-oxime's versatility and reactivity make it a valuable tool in chemical research, where it can be used to study reaction mechanisms, explore new synthetic pathways, and develop innovative chemical processes.

InChI:InChI=1/C8H8N2O2/c11-8(6-9-12)10-7-4-2-1-3-5-7/h1-6,12H,(H,10,11)/b9-6+

Upstream product

• 302-17-0 chloral hydrate 
• 62-53-3 aniline 
• 75-87-6 chloral 
• 7732-18-5 water 
• 412028-64-9 2-anilino-2-oxoethanehydroxymoyl chloride 
• 5470-11-1 hydroxylamine hydrochloride 
• 2565-30-2 formyl chloride 
• 220898-58-8 N⁽¹⁾-phenyl-2-amino-2-hydroxyiminoacetamide 

Downstream Products

• 607-28-3 (E)-1H-indole-2,3-dione 3-oxime 
• 6784-22-1 phenylcarbamoyl cyanide 
• 555-48-6 2-amino-N-phenyl-acetamide 
• 412028-64-9 2-anilino-2-oxoethanehydroxymoyl chloride 
• 6579-43-7 hydroxyimino-acetic acid-(2,4-dinitro-anilide) 
• 91-56-5 indole-2,3-dione 
• 4801-39-2 2-amino-N-phenylacetamide hydrochloride 
• 10319-52-5 5-imino-1,3-diphenyl-imidazolidine-2,4-dione 
• 37466-55-0 2-hydroxyimino-3-morpholin-4-yl-N-phenyl-propionamide 
• 50-00-0 formaldehyd 
• 7803-49-8 hydroxylamine 
• 62-53-3 aniline 
• 2058-74-4 1-methyl-1H-indole-2,3-dione 
• 79560-71-7 isatin-3-(4-chlorophenyl)thiosemicarbazone 

Relevant articles and documents

Design, synthesis, and in vitro and in vivo anti-angiogenesis study of a novel vascular endothelial growth factor receptor-2 (VEGFR-2) inhibitor based on 1,2,3-triazole scaffold

In the past five years, our team had been committed to click chemistry research, exploring the biological activity of 1,2,3-triazole by synthesizing different target inhibitors. In this study, a series of novel indole-2-one derivatives based on 1,2,3-triazole scaffolds were synthesized for the first time, and their inhibitory activity on vascular endothelial growth factor receptor-2 (VEGFR-2) was tested. Most of the compounds had shown promising activity in the VEGFR-2 kinase assay and had low toxicity to human umbilical vein endothelial cells (HUVECs). The compound 13d (IC50 = 26.38 nM) had better kinase activity inhibition ability than sunitinib (IC50 = 83.20 nM) and was less toxic to HUVECs. Moreover, it had an excellent inhibitory effect on HT-29 and MKN-45 cells. On the one hand, by tube formation assay, transwell, and Western blot analysis, compound 13d could inhibit VEGFR-2 protein phosphorylate on HUVECs, thereby inhibiting HUVECs migration and tube formation. In vivo study, the zebrafish model with VEGFR-2 labeling also verified that compound 13d had more anti-angiogenesis ability than sunitinib. On the other hand, molecular docking and molecular dynamics (MD) simulation results showed that compound 13d could stably bind to the active site of VEGFR-2. Based on the above findings, compound 13d could be considered an effective anti-angiogenesis drug and has more development value than sunitinib.

Synthesis of substituted tryptanthrin via aryl halides and amines as antitumor and anti-MRSA agents

The natural alkaloid, tryptanthrin (indolo[2,1-b]quinazoline-6,12-dione), and its analogues are found to exhibit potent antitumor and anti-MRSA activities. An efficient and convenient method has been developed for the synthesis of tryptanthrin D-ring derivatives through the reaction of substituted tryptanthrins and secondary amines in moderate to good yields. Some of the new compounds exhibited antitumor activities against the human tumor cell lines A549, HCT116 and MDA-MB-231, with mean IC50 values at low micromolar levels. In addition, some of the compounds showed excellent anti-MRSA activities and were more effective than vancomycin, with MIC values of 0.31–1.25 μg/mL for Mu50,RN4220, and Newman strains.

Design and development of Isatin-triazole hydrazones as potential inhibitors of microtubule affinity-regulating kinase 4 for the therapeutic management of cell proliferation and metastasis

Microtubule affinity-regulating kinase 4 (MARK4) is a potential drug target as the same is found to be over expressed in several types of cancers. In search of effective MARK4 inhibitors, we have synthesized and characterized Isatin-triazole hydrazones (9a-i) and evaluated their inhibitory potential. Of all the compounds, 9g showed better binding affinity and enzyme inhibition potential in sub micromolar range. Human serum albumin (HSA) binding assay suggested an easy transportation of 9g in blood stream due to its binding affinity. In vitro anticancer studies performed on MCF-7, MDA-MB-435s and HepG2 cells using 9g showed inhibition of cell proliferation and cell migration. Further, 9g induces apoptosis in these cancerous cells, with IC50 values of 6.22, 9.94 and 8.14 μM, respectively. Putatively, 9g seems to cause oxidative stress resulting in apoptosis. Functional assay of 9g with a panel of 26 kinases showed MARK4 specific profile. In conclusion, 9g seems to possess an effective inhibitory potential towards MARK4 adding an additional repertoire to anticancer therapeutics.

Synthesis and Ameliorative Effect of Isatin–Mesalamine Conjugates on Acetic Acid-induced Colitis in Rats

A series of new isatin–mesalamine conjugates (9a–g) were synthesized via conjugation of isatin (3a) and its derivatives (3b–3d, 4, 5, and 6) with mesalamine (7) by using chloroacetyl chloride as a bifunctional linker. Compounds 3a–3d were prepared by employing Sandmeyer reaction. Compounds 4, 5, and 6 were obtained from isatin (3a) via previously reported methods. The synthesized compounds were characterized by IR, mass, 1H NMR, and 13C NMR spectral techniques. Synthesized compounds (3a–d, 4, 5, 6, and 9a–g) were evaluated for in vitro antioxidant activity by DPPH assay method using ascorbic acid as standard. Hybrids 9b (IC50?=?368.6?±?3.5?μM) and 9f (IC50?=?335.1?±?2.9?μM) showed better antioxidant activity than its parent compounds such as 3a (IC50?=?556.8?±?2.9?μM), 5 (IC50?=?511.9?±?3.6?μM), and 7 (IC50?=?768.9?±?2.7?μM). Acetic acid-induced ulcerative colitis in rat model was chosen to examine the antioxidant potential of the synthesized hybrids (9b and 9f) in the amelioration of ulcerative colitis. Colonic myeloperoxidase and malondialdehyde enzymes were used as biomarkers of anti-ulcerative colitis activity. In the present study, hybrids 9b and 9f reduced the levels of colonic myeloperoxidase and malondialdehyde enzymes significantly (p??0.05) when compared with control (colitic), at a dose (0.03?mM/12.5?mg/kg b.w. p.o.) (50%) less than that of its parent moieties mesalamine (0.16?mM/25?mg/kg) and isatin (0.16?mM/25?mg/kg). Thus, the molecular hybridization was proved to be significant in enhancing the activity of hybrids 9b and 9f by reducing the dose.

Indazole compounds and preparation method and application thereof

The invention provides indazole compounds and a preparation method and application thereof. A series of completely new small molecule PI3Kdelta inhibitors are designed and synthesized by using indazole as a structural mother nucleus, the PI3Kdelta kinase inhibitory activity test and MV-4-11 cell activity test of the compounds are carried out, and the indazole compounds exhibit better kinase subtype selectivity, and exhibit better in vitro proliferation inhibitory activity against tumor cell lines. The compounds can be used in the preparation of antitumor drugs and in the preparation of activedrugs for inhibiting PI3Kdelta kinase, and a new way is provided for the antitumor drug research. The raw materials are cheap and easy to obtain, the preparation method is simple, and the large-scaleproduction is suitable. The structural formula is as shown in the specification.

Design, synthesis and QSAR study of novel isatin analogues inspired Michael acceptor as potential anticancer compounds

Molecular hybridization is considered as an effective tactic to develop drugs for the treatment of cancer. A series of novel hybrid compounds of isatin and Michael acceptor were designed and synthesized on the basis of association principle. These hybrid compounds were tested for cytotoxic potential against human cancer cell lines namely, BGC-823, SGC-7901 and NCI-H460 by MTT assay. Most compounds showed good anti-growth activities in all tested human cancer cells. SAR and QSAR analysis may provide vital information for the future development of novel anti-cancer inhibitors. Notably, compound 6a showed potent growth inhibition on BGC-823, SGC-7901 and NCI-H460 with the IC50 values of 3.6 ± 0.6, 5.7 ± 1.2, 3.2 ± 0.7 μM, respectively. Besides, colony formation assays, wound healing assays and flow cytometry analysis indicated 6a exhibited a potent anti-growth and anti-migration ability in a concentration-dependence manner through arrested cells in the G2/M phase of cell cycle. Moreover, 6a significantly repressed tumor growth in a NCI-H460 xenograft mouse model. Overall, our findings suggested isatin analogues inspired Michael acceptor may provide promising lead compounds for the development of cancer chemotherapeutics.

Palladium(II)/N-Heterocyclic Carbene Catalyzed One-Pot Sequential α-Arylation/Alkylation: Access to 3,3-Disubstituted Oxindoles

Rationally designed fluorene-based mono- and bimetallic Pd-PEPPSI complexes were synthesized and demonstrated to be effective for the one-pot sequential α-arylation/alkylation of oxindoles. This streamlined approach offers efficient access to functionalized 3,3-disubstituted oxindoles in excellent yields (up to 89%) under mild reaction conditions.

Design, Synthesis, Characterization, and In Vitro Evaluation of Isatin-Pomalidomide Hybrids for Cytotoxicity against Multiple Myeloma Cell Lines

Inspired by the concept of molecular hybridization, a series of new isatin-pomalidomide hybrids (9a–9g) were designed, synthesized, characterized, and evaluated for in vitro cytotoxic activity against U266B1 and RPMI 8226 multiple myeloma cell lines. Sandmeyer methodology and N-halomethylketo alkylation reaction are the two important reactions involved in the synthesis of isatin-pomalidomide hybrids (9a–9g). All the synthesized compounds (3a–3d, 4, 5, 6, and 9a–9g) were characterized by using IR, mass, 1H-NMR, and 13C-NMR spectral techniques. The efficacy of all the synthesized compounds was tested against the aforementioned cell lines by employing MTT assay (3-(4,5-dimethylthiazol-2-yl)-2,5-diphenyltetrazolium bromide) standard protocols while using pomalidomide as a standard. The test concentrations used in the MTT assay were 1, 10, 20, 30, and 40?μM, and the period of incubation was 24?h. All the synthesized compounds were found to have moderate to greater cytotoxic activity against the aforementioned cell lines. Among them, synthesized hybrids 9f (IC50, U266B1?=?5.15?±?0.72?μM, RPMI8226?=?11.66?±?0.79?μM) and 9g (IC50, U266B1?=?2.50?±?0.37?μM, RPMI8226?=?6.70?±?0.55?μM) displayed better cytotoxic activity against both the cell lines used in the present study.

Synthesis and cytotoxic studies of novel 5-phenylisatin derivatives and their anti-migration and anti-angiogenic evaluation

A number of 5-arylisatin derivatives were synthesized in 5–6 steps from readily available starting materials. Their structures were confirmed by 1H NMR and 13C NMR as well as LC/MS. The cytotoxicity of these novel isatins against human leukemia K562 cells were evaluated by MTT assay in vitro. SAR studies indicated that the N-substituted benzyl and C-5 substituted phenyl groups greatly enhance their cytotoxic activity, whereas an intact carbonyl functionality on C-3 present in the parent ring is required to maintain such a potency. Particularly, N-(p-methoxybenzyl)-5-(p-methoxyphenyl)isatin (compound 2m) showed the highest antitumor activity against K562 cell lines (IC50 = 0.03 μM). Moreover, treatment with compound 2m significantly inhibited liver cancer HepG2 cells proliferation and migration, which could also reduce the human umbilical vein endothelial cells (HUVEC) tube formation. In conclusion, compound 2m exhibited very good cancer cells proliferation inhibition by angiogenesis responses in vitro, and 2m might be a promising angiogenesis inhibitor for cancer treatment.

Application of isatin analogues in preparing antineoplastic drugs

The invention belongs to the field of medicinal chemistry, and in particular relates to an application of isatin analogues in preparing antineoplastic drugs. A series of isatin analogues can be synthesized by splicing isatin and [alpha],[beta]-unsaturated ketone via a medicinal chemistry splicing principle. The compounds (the isatin analogues) are relatively good in inhibitory activity on three tumor cells, and an antineoplastic effect can be achieved by inhibiting growth and migration of tumor cells and by blocking cell cycle G2/M period; and based upon in vivo experimental results, it is also indicated that the compounds can inhibit tumor growth.