39978-57-9

Basic information

• Product Name: 5-Nitrothiophene-2-carbonyl Chloride
• Synonyms: 5-Nitro-2-thenoyl Chloride;5-Nitro-2-thiophenecarbonyl Chloride;5-Nitrothiophene-2-carbonyl Chloride;5-Nitrothiophene-2-carboxylic Acid Chloride;5-Nitrothiophene-2-formyl Chloride
• CAS NO: 39978-57-9
• Molecular Formula: C₅H₂ClNO₃S
• Molecular Weight: 191.59
• Product Categories: Heterocyclic Compounds;Heterocycles;Inhibitors;Sulfur & Selenium Compounds
• Mol File: 39978-57-9.mol

Chemical Properties

• Boiling Point: 299.523°C at 760 mmHg
• Flash Point: 134.947°C
• Appearance: /
• Density: 1.635g/cm³
• Vapor Pressure: 0.001mmHg at 25°C
• Refractive Index: 1.625
• CAS DataBase Reference: 5-Nitrothiophene-2-carbonyl Chloride(CAS DataBase Reference)
• NIST Chemistry Reference: 5-Nitrothiophene-2-carbonyl Chloride(39978-57-9)
• EPA Substance Registry System: 5-Nitrothiophene-2-carbonyl Chloride(39978-57-9)

Safety Data

• Hazardous Substances Data: 39978-57-9(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
5-Nitrothiophene-2-carbonyl Chloride is used as a thiophene building block for the synthesis of various pharmaceutical compounds. Its unique structure and reactivity allow for the creation of a wide range of molecules with potential therapeutic applications.
Used in the Synthesis of Raltitrexed:
One of the primary applications of 5-Nitrothiophene-2-carbonyl Chloride is as an intermediate in the production of raltitrexed, a potent inhibitor of thymidylate synthase. Raltitrexed is a chemotherapeutic agent used in the treatment of colorectal cancer, and its synthesis relies on the incorporation of this key intermediate.

InChI:InChI=1/C5H2ClNO3S/c6-5(8)3-1-2-4(11-3)7(9)10/h1-2H

Upstream product

• 6317-37-9 5-nitrothiophene-2-carboxylic acid 
• 527-72-0 2-thiophenylcarboxylic acid 
• 16689-02-4 5-nitro-2-thienyl cyanide 
• 4521-33-9 5-nitro-2-thiophenecarboxaldehyde 

Downstream Products

• 79822-86-9 N-phenyl-5-nitro-2-thiophenecarboxamide 
• 5832-00-8 5-nitrothiophene-2-carboxamide 
• 83851-86-9 (5-nitro-2-thenoyl)-DL-Phe-OMe 
• 89266-28-4 [2-(5-Nitro-thiophene-2-carbonyloxy)-benzyl]-triphenyl-phosphonium; bromide 
• 89266-32-0 [5-Methoxy-2-(5-nitro-thiophene-2-carbonyloxy)-benzyl]-triphenyl-phosphonium; bromide 
• 89266-36-4 [5-Chloro-2-(5-nitro-thiophene-2-carbonyloxy)-benzyl]-triphenyl-phosphonium; bromide 
• 891845-32-2 cyclohexyl 5-nitro-2-thiophenecarboxylate 
• 112523-47-4 N-phenyl-5-nitro-2-thiophenecarbothioamide 
• 117283-71-3 5-Nitro-thiophene-2-carboxylic acid [1-(2-hydroxy-3-phenoxy-propyl)-1H-benzoimidazol-2-yl]-amide 

Relevant articles and documents

Bayesian Modeling and Intrabacterial Drug Metabolism Applied to Drug-Resistant Staphylococcus aureus

We present the application of Bayesian modeling to identify chemical tools and/or drug discovery entities pertinent to drug-resistant Staphylococcus aureus infections. The quinoline JSF-3151 was predicted by modeling and then empirically demonstrated to be active against in vitro cultured clinical methicillin- and vancomycin-resistant strains while also exhibiting efficacy in a mouse peritonitis model of methicillin-resistant S. aureus infection. We highlight the utility of an intrabacterial drug metabolism (IBDM) approach to probe the mechanism by which JSF-3151 is transformed within the bacteria. We also identify and then validate two mechanisms of resistance in S. aureus: one mechanism involves increased expression of a lipocalin protein, and the other arises from the loss of function of an azoreductase. The computational and experimental approaches, discovery of an antibacterial agent, and elucidated resistance mechanisms collectively hold promise to advance our understanding of therapeutic regimens for drug-resistant S. aureus.

Pine Rosin as a Valuable Natural Resource in the Synthesis of Fungicide Candidates for Controlling Fusarium oxysporum on Cucumber

To improve the effect of pine rosin in plant fungicides, four series of dehydroabietyl-1,3,4-thiadiazole derivatives from the natural product rosin were synthesized. Based on the evaluation of the in vitro antifungal activity against Sclerotinia sclerotiorum, Botrytis cinerea, Fusarium oxysporum, and Magnaporthe oryzae, rosin-based 1,3,4-thiadiazole compounds containing thiophene heterocycles were screened. Notably, compound 3e [dehydroabietyl-(1,3,4-thiadiazol-2-yl)-5-nitrothiophene-2-carboxamide] exhibited excellent antifungal property against F. oxysporum with an EC50 of 0.618 mg/L, which was lower than that of the positive control carbendazim (0.649 mg/L). The in vivo antifungal activity results showed that 3e exerted a protective effect on cucumber plants. Physiological and biochemical studies showed that the primary mechanism of action of compound 3e on F. oxysporum was it changed the mycelial morphology, increased the cell membrane permeability, and inhibited the synthesis of ergosterol in the mycelia. Furthermore, the quantitative structure-activity relationship studies revealed that the frontier orbital energy in the molecule had a key role in the antifungal activity through the conjugation and electrostatic interaction between compound 3e and the receptors of the target. Thus, the present study highlighted the application of rosin-based fungicidal candidates and exploited efficient plant pesticides for sustainable crop production.

Antifungal Application of Rosin Derivatives from Renewable Pine Resin in Crop Protection

In the current work, we synthesized two series of dehydroabietyl amide derivatives from natural product rosin and evaluated their antifungal effects on Valsa mali, Phytophthora capsici, Botrytis cinerea, Sclerotinia sclerotiorum, and Fusarium oxysporum. In vitro and in vivo antifungal activities results indicated that rosin-based amide compounds containing thiophene heterocycles had better inhibitory effects on B. cinerea. In particular, compound 5b (5-fluoro-2-thiophene dehydroabietyl amide) exhibited the excellent antifungal properties against B. cinerea with an EC50 of 0.490 mg/L, which was lower compared to the positive control penthiopyrad (0.562 mg/L). Physiological and biochemical studies showed that the primary action mechanism of compound 5b on B. cinerea changes mycelial morphology, increases cell membrane permeability, and inhibits the TCA pathway in respiratory metabolism. Furthermore, QSAR and SAR studies revealed that charge distribution of rosin-based amides derivatives have a key role in the antifungal activity through the hydrogen bonding, conjugation, and electrostatic interaction between the compounds and the receptors of the target. To sum up, this study contributes to the development of rosin-based antifungal agents with a novel structure and preferable biological activity.

Raltitrexed-related substance F and preparation and applications thereof

The invention discloses a Raltitrexed-related substance F with raltitrexed with dihydrofolate reductase and methionine synthetase inhibitory activity, a preparation method thereof, and an applicationof the Raltitrexed-related substance F as an impurity reference substance.

Raltitrexed impurity C and preparation and application thereof

The invention discloses a potential blood system toxic impurity C of Raltitrexed, a preparation method thereof, and an application of the impurity C as an impurity reference substance.

Raltitrexed pharmaceutical composition and preparation method thereof

The invention relates to a raltitrexed pharmaceutical composition which is high in safety and a preparation method thereof. The raltitrexed pharmaceutical composition comprises raltitrexed and thiophene related substances, wherein the content of the thiophene related substances is not higher than 0.3%. The raltitrexed pharmaceutical composition is good in safety, effectiveness and stability and can relieve the blood toxicity of the raltitrexed to a certain degree.

Structure-antibacterial activity relationships of n-substituted-(D-/l-alaninyl) 1h-1,2,3-triazolylmethyl oxazolidinones

Bacterial resistance towards the existing class of antibacterial drugs continues to increase, posing a significant threat to the clinical usefulness of these drugs. These increasing and alarming rates of antibacterial resistance development and the decline in the number of new antibacterial drugs’ approval continue to serve as a major impetus for research into the discovery and development of new antibacterial agents. We synthesized a series of D-/L-alaninyl substituted triazolyl oxazolidinone derivatives and evaluated their antibacterial activity against selected standard Gram-positive and Gram-negative bacterial strains. Overall, the compounds showed moderate to strong antibacterial activity. Compounds 9d and 10d (D-and L-alaninyl derivatives bearing the 3,5-dinitrobenzoyl substituent), 10e (L-alaninyl derivative bearing the 5-nitrofurancarbonyl group) and 9f and 10f (D-and L-alaninyl derivatives bearing the 5-nitrothiophene carbonyl moiety) demonstrated antibacterial activity (MIC: 2 μg/mL) against Staphylococcus aureus, Staphylococcus epidermidis, Enterococcus faecalis and Moraxella catarrhalis standard bacterial strains. No significant differences were noticeable between the antibacterial activity of the D-and L-alaninyl derivatives as a result of the stereochemistry of the compounds.

Impurity A of raltitrexed, and preparation method and application thereof

The invention discloses a potential blood system toxic impurity A of raltitrexed, a preparation method thereof, and a use of the impurity A as an impurity reference substance.

Development of novel tetrahydrothieno[2,3-c]pyridine-3-carboxamide based Mycobacterium tuberculosis pantothenate synthetase inhibitors: Molecular hybridization from known antimycobacterial leads

Twenty six 2,6-disubstituted 4,5,6,7-tetrahydrothieno[2,3-c]pyridine-3- carboxamide derivatives were designed by molecular hybridization approach using and synthesized from piperidin-4-one by five step synthesis. Compounds were evaluated for Mycobacterium tuberculosis (MTB) pantothenate synthetase (PS) inhibition study, in vitro activities against MTB, cytotoxicity against RAW 264.7 cell line. Among the compounds, 6-(4-nitrophenylsulfonyl)-2-(5- nitrothiophene-2-carboxamido)-4,5,6,7-tetrahydrothieno[2,3-c] pyridine-3-carboxamide (11) was found to be the most active compound with IC50 of 5.87 ± 0.12 μM against MTB PS, inhibited MTB with MIC of 9.28 μM and it was non-cytotoxic at 50 μM. The binding affinity of the most potent inhibitor 11 was further confirmed biophysically through differential scanning fluorimetry.

Synthesis, antileishmanial and antitrypanosomal activities of N-substituted tetrahydro-β-carbolines

A series of N-substituted tetrahydro-β-carbolines were synthesized and screened for antileishmanial activity through an in vitro assay that involves promastigotes and axenic amastigotes of Leishmania donovani, the causative agent for visceral leishmaniasis. The thiophen-2-yl analogs 9b and 11f and naphthyl analog 11h were found to show significant activity against promastigotes with IC50 values of 12.7, 9.1 and 22.1 μM, respectively. Analogs 9b and 11h were also effective against axenic amastigotes with IC50 values of 62.8 and 87.6 μM, respectively. The antileishmanial activity of analogs was then tested in human macrophage cell line infected with L. donovani amastigotes and 2-naphthyl linked analog 11h was found to be effective with IC50 value of 28.3 μM. Several analogs also displayed antitrypanosomal activity against Trypanosoma brucei, the causative agent for human African trypanosomiasis. Compounds 11e, 11f and 11h were more effective than others with IC50 values of 1.0, 8.9 and 10.2 μM, respectively. All synthesized analogs were not cytotoxic towards mammalian cell lines including Vero (monkey kidney fibroblasts), HEPG2 (human hepatoma cells), LLC-PK1 (pig kidney epithelial cells) and THP-1 (human macrophages).