1245649-52-8

Basic information

• Product Name: 4-CHLORO-5-NITRO-1-(PHENYLSULFONYL)-1H-PYRROLO[2,3-B]PYRIDINE
• Synonyms: 4-CHLORO-5-NITRO-1-(PHENYLSULFONYL)-1H-PYRROLO[2,3-B]PYRIDINE;1-(benzenesulfonyl)-4-chloro-5-nitropyrrolo[2,3-b]pyridine;1-(benzenesulfonyl)-4-chloro-5-nitro-1H-pyrrolo[2,3-b]pyridine;4-Chloro-5-nitro-1-(phenylsulfonyl);4-Chloro-5-nitro-1-(phenylsulfonyl)-7-azaindole;1H-Pyrrolo[2,3-b]pyridine, 4-chloro-5-nitro-1-(phenylsulfonyl)-
• CAS NO: 1245649-52-8
• Molecular Formula: C₁₃H₈ClN₃O₄S
• Molecular Weight: 337.73832
• EINECS: -0
• Mol File: 1245649-52-8.mol

Chemical Properties

• Boiling Point: 539.9±60.0 °C(Predicted)
• Appearance: /
• Density: 1.63±0.1 g/cm3(Predicted)
• Storage Temp.: under inert gas (nitrogen or Argon) at 2-8°C
• PKA: -0.67±0.30(Predicted)
• CAS DataBase Reference: 4-CHLORO-5-NITRO-1-(PHENYLSULFONYL)-1H-PYRROLO[2,3-B]PYRIDINE(CAS DataBase Reference)
• NIST Chemistry Reference: 4-CHLORO-5-NITRO-1-(PHENYLSULFONYL)-1H-PYRROLO[2,3-B]PYRIDINE(1245649-52-8)
• EPA Substance Registry System: 4-CHLORO-5-NITRO-1-(PHENYLSULFONYL)-1H-PYRROLO[2,3-B]PYRIDINE(1245649-52-8)

Safety Data

• Hazardous Substances Data: 1245649-52-8(Hazardous Substances Data)

Usage

Uses

Used in Chemical Research:
4-Chloro-5-nitro-1-(phenylsulfonyl)-1H-pyrrolo[2,3-b]pyridine is used as a reagent for various chemical syntheses, particularly in the development of new compounds and materials. Its unique structural formation allows it to participate in a range of reactions, making it a valuable tool in the field of chemistry.
Used in Pharmaceutical Industry:
4-Chloro-5-nitro-1-(phenylsulfonyl)-1H-pyrrolo[2,3-b]pyridine is used as an intermediate in the synthesis of pharmaceutical compounds. Its potential reactivity and functional groups make it a candidate for the development of new drugs and therapeutic agents.
Used in Material Science:
4-Chloro-5-nitro-1-(phenylsulfonyl)-1H-pyrrolo[2,3-b]pyridine is used as a building block in the creation of new materials with specific properties. Its unique structure and reactivity contribute to the development of advanced materials for various applications, such as electronics, coatings, and adhesives.

Upstream product

• 744209-63-0 1-(benzenesulfonyl)-4-chloro-1H-pyrrolo[2,3-b]pyridine 
• 55052-28-3 4-chloro-7-azaindole 
• 271-63-6 7-Azaindole 
• 98-09-9 benzenesulfonyl chloride 

Downstream Products

• 1315495-05-6 4-(1-benzenesulphonyl-5-nitro-1H-pyrrolo[2,3-b]pyridine-4ylamino)piperidine-1-carboxylic acid tert-butyl ester 
• 1383729-54-1 4-(3-benzenesulfonyl-7,8-dioxo-3,6,7,8-tetrahydro-3,4,6,9-tetraazacyclopenta[a]naphthalen-9-yl)piperidine-1-carboxylic acid tert-butyl ester 
• 1383729-55-2 3-benzenesulfonyl-9-piperidin-4-yl-6,9-dihydro-3H-3,4,6,9-tetraazacyclopenta[a]naphthalene-7,8-dione 
• 1383729-56-3 3-[4-(3-benzenesulfonyl-7,8-dioxo-3,6,7,8-tetrahydro-3,4,6,9-tetraazacyclopenta[a]naphthalen-9-yl)piperidin-1-yl]propionitrile 
• 1383729-58-5 3-[4-(3-benzenesulfonyl-7-chloro-8-oxo-3,8-dihydro-3,4,6,9-tetraazacyclopenta[a]naphthalen-9-yl)piperidin-1-yl]propionitrile 
• 1383729-60-9 3-[4-(7-amino-3-benzenesulfonyl-8-oxo-3,8-dihydro-3,4,6,9-tetraazacyclopenta[a]naphthalen-9-yl)piperidin-1-yl]propionitrile 
• 1383729-61-0 4-(3-benzenesulfonyl-7-chloro-8-oxo-3,8-dihydro-3,4,6,9-tetraazacyclopenta[a]naphthalen-9-yl)piperidine-1-carboxylic acid tert-butyl ester 
• 1383729-62-1 4-(3-benzenesulfonyl-7-dimethylamino-8-oxo-3,8-dihydro-3,4,6,9-tetraazacyclopenta[a]naphthalen-9-yl)piperidine-1-carboxylic acid tert-butyl ester 
• 1383729-63-2 3-benzenesulfonyl-7-dimethylamino-9-piperidin-4-yl-3,9-dihydro-3,4,6,9-tetraazacyclopenta[a]naphthalen-8-one 
• 1383729-64-3 3-[4-(3-benzenesulfonyl-7-dimethylamino-8-oxo-3,8-dihydro-3,4,6,9-tetraazacyclopenta[a]naphthalen-9-yl)piperidin-1-yl]propionitrile 
• 1383729-65-4 3-benzenesulfonyl-9-(1-tert-butoxycarbonyl-piperidin-4-yl)-8-oxo-8,9-dihydro-3H-3,4,6,9-tetraazacyclopenta[a]naphthalene-7-carboxylic acid ethyl ester 
• 1383729-66-5 3-benzenesulfonyl-8-oxo-9-piperidin-4-yl-8,9-dihydro-3H-3,4,6,9-tetraazacyclopenta[a]naphthalene-7-carboxylic acid ethyl ester 
• 1383729-67-6 3-benzenesulfonyl-8-oxo-9-(1-pyridin-3-ylmethyl-piperidin-4-yl)-8,9-dihydro-3H-3,4,6,9-tetraazacyclopenta[a]naphthalene-7-carboxylic acid ethyl ester 
• 1383729-69-8 3-[4-(3-benzenesulfonyl-7-methoxy-8-oxo-3,8-dihydro-3,4,6,9-tetraazacyclopenta[a]naphthalen-9-yl)piperidin-1-yl]propionitrile 

Relevant articles and documents

NOVEL HYDRAZONE DERIVATIVE WITH ARYL OR HETEROARYL GROUP SUBSTITUTED AT TERMINAL AMINE GROUP THEREOF AND USE THEREOF

The present invention relates to novel hydrazone derivatives in which a terminal amine group is substituted with an aryl group or a heteroaryl group, and uses thereof.

Discovery of imidazopyrrolopyridines derivatives as novel and selective inhibitors of JAK2

Herein, we describe the design, synthesis, and structure?activity relationships of a series of imidazopyrrolopyridines derivatives that selectively inhibit Janus kinase 2 (JAK2). These screening cascades revealed that 6k was a preferred compound, with IC50 values of 10 nM for JAK2. Moreover, 6k was a selective JAK2 inhibitor with 19-fold, >30-fold and >30-fold selectivity over JAK1, JAK3 and TYK2 respectively. In cytokine-stimulated cell-based assays, 6k exhibited a higher JAK2 selectivity over JAK1 isoforms. Indeed, at a dose of 20 mg/kg compound 6k, pSTAT3 and pSTAT5 expression was reduced to levels comparable to those of control animals untreated with GM-CSF. Additionally, 6k showed a relatively good bioavailability (F = 38%), a suitable half-life time (T1/2 = 1.9 h), a satisfactory metabolic stability, suggesting that 6k might be a promising inhibitor of JAK2 for further development research for the treatment of MPNs.

Design and synthesis of 7-azaindole derivatives and their antitumor and analgesic activities

To develop effective anti-tumor and analgesic drugs, a series of novel 7-azaindole derivatives were designed and synthesized through a four-step reaction. 18 target compounds were obtained and characterized through Nuclear Magnetic Resonance and High Resolution Mass Spectrometry. Their anti-proliferative activities and analgesic effect were evaluated. When the 1-position was a methylsulfonyl group and the 5-position was a nitro group, compound 4f demonstrated the best activity. Furthermore, there was a dramatic difference between the IC50 values of compound 4f in tumor and in healthy cell line. The IC50 values of compound 4f in MCF7 breast cancer cell line was 5.781 μmol/L and 8.077 μmol/L in HepG2 hepatoma carcinoma cell line, but more than 100 μmol/L in HL7702 liver cell line. Preliminary results showed that compounds 3a, 3g and 4i had significant analgesic effects in mice, which were stronger than aspirin. These compounds have good prospects for new drug development.

Novel hydrazone derivatives comprising aryl or heteroaryl group substituted at terminal amine and use thereof

The present invention relates to novel hydrazone derivatives with an aryl or heteroaryl group substituted at a terminal amine group thereof and a use thereof.

A new synthetic process of the pyrrole compounds and the use of the anti-tumor effect (by machine translation)

The present invention discloses a new synthetic process of the pyrrole compounds and the use of the anti-tumor effect, and in particular relates to compounds 1 - benzenesulfonyl - 4 - chloro - 5 - nitro - 1 H - pyrrolo [2, 3 - b] pyridine, hydrate and its salt of new synthetic process and the use of the anti-tumor effect, this synthesis process takes 1 H - pyrrolo [2, 3 - b] pyridine as the starting material, after chloro-, prepared by acylation reaction such as 1 - benzenesulfonyl - 4 - chloro - 5 - nitro - 1 H - pyrrolo [2, 3 - b] pyridine, hydrate and its salt, provides a simple operation, high yield of the new process, the preparation method is simple, mild reaction conditions, at the same time the compound anti-tumor activity is prominent, little toxicity to normal cell, is favorable to its anti-tumor field widely popularized. (by machine translation)

Discovery of 3-Cyano- N-(3-(1-isobutyrylpiperidin-4-yl)-1-methyl-4-(trifluoromethyl)-1 H-pyrrolo[2,3- b]pyridin-5-yl)benzamide: A Potent, Selective, and Orally Bioavailable Retinoic Acid Receptor-Related Orphan Receptor C2 Inverse Agonist

The nuclear hormone receptor retinoic acid receptor-related orphan C2 (RORC2, also known as RORγt) is a promising target for the treatment of autoimmune diseases. A small molecule, inverse agonist of the receptor is anticipated to reduce production of IL-17, a key proinflammatory cytokine. Through a high-throughput screening approach, we identified a molecule displaying promising binding affinity for RORC2, inhibition of IL-17 production in Th17 cells, and selectivity against the related RORA and RORB receptor isoforms. Lead optimization to improve the potency and metabolic stability of this hit focused on two key design strategies, namely, iterative optimization driven by increasing lipophilic efficiency and structure-guided conformational restriction to achieve optimal ground state energetics and maximize receptor residence time. This approach successfully identified 3-cyano-N-(3-(1-isobutyrylpiperidin-4-yl)-1-methyl-4-(trifluoromethyl)-1H-pyrrolo[2,3-b]pyridin-5-yl)benzamide as a potent and selective RORC2 inverse agonist, demonstrating good metabolic stability, oral bioavailability, and the ability to reduce IL-17 levels and skin inflammation in a preclinical in vivo animal model upon oral administration.

TRICYCLIC HETEROCYLIC DERIVATIVES

Compounds of the formula (I) in which R1 and R2 have the meanings indicated in Claim 1,are inhibitors of ATR, and can be employed for the treatment of diseases such as cancer.

METHOXY-SUBSTITUTED PYRROLOPYRIDINE MODULATORS OF RORC2 AND METHODS OF USE THEREOF

The present invention provides methoxy-substituted pyrrolopyridines, pharmaceutical compositions thereof, methods of modulating RORγ activity and/or reducing the amount of IL- 17 in a subject, and methods of treating various medical disorders using such pyrrolopyridines and pharmaceutical compositions thereof.

RORC2 INHIBITORS AND METHODS OF USE THEREOF

The present invention provides compounds, pharmaceutical compositions, methods of inhibiting RORγ activity and/or reducing the amount of IL-17 in a subject, and methods of treating various medical disorders using such compounds and pharmaceutical compositions.

Aminosulfonylmethylcyclohexanes as JAK inhibitors

The invention relates to a compound of formula wherein the variables have the meaning as indicated in the claims; in free form and in salt form; and optionally the enantiomers and geometrical isomers thereof. The compounds of formula (I) are useful as therapeutic agent for organ transplants, lupus, multiple sclerosis, rheumatoid arthritis, psoriasis, Type I diabetes and complications from diabetes, cancer, asthma, atopic dermatitis, autoimmune thyroid disorders, ulcerative colitis, inflammatory bowel diseases, Crohn's disease, Alzheimer's disease, leukemia, osteoarthritis, control of pruritus, chronic respiratory disease or keratoconjunctivitis in mammals.