4-Chloro-1h-pyrrolo[2,3-b]pyridine-3-carbaldehyde (918515-16-9)

This product(s) resides on a APICMO contract.

The ability to produce, synthesize and manufacture large quantities of  4-Chloro-1h-pyrrolo[2,3-b]pyridine-3-carbaldehyde (918515-16-9) with quality control system under CGMP manufacturing
regulations.

Category:

Description

 4-Chloro-1h-pyrrolo[2,3-b]pyridine-3-carbaldehyde (918515-16-9) video

Janus kinases (JAKs) play a crucial role in cytokine mediated signal transduction. JAK inhibitors have emerged as effective immunomodulative agents for the prevention of transplant rejection. We previously reported that the tricyclic imidazo-pyrrolopyridinone 2 is a potent JAK inhibitor; however, it had poor oral absorption due to low membrane permeability. Here, we report the structural modification of compound 2 into the tricyclic dipyrrolopyridine 18a focusing on reduction of polar surface area (PSA), which exhibits potent in vitro activity, improved membrane permeability and good oral bioavailability. Compound 18a showed efficacy in rat heterotopic cardiac transplants model.

This product(s) resides on a APICMO contract. If you are viewing this page as a non-registered user, the price(s) displayed is List Price. To view your pricing, log in using your account number, or become a registered user by contacting one of our Customer Service teams. To place an order, contact APICMO Customer Service.

 4-Chloro-1h-pyrrolo[2,3-b]pyridine-3-carbaldehyde (918515-16-9) Specifications

CAS 918515-16-9
CAS Min % 95%
CAS Max % 100%
MDL Number MFCD09880129
InChI Key DYWWVLQMUUZZRJ-UHFFFAOYSA-N
Chemical Name or Material  4-Chloro-1h-pyrrolo[2,3-b]pyridine-3-carbaldehyde
Infrared Spectrum Authentic
Physical Form White to brown solid
Packaging Glass bottle
Molecular Formula C8H5N2OCl
Molecular Weight (g/mol) 180.594
SMILES ClC1(=C2(C(=NC=C1)NC=C2C=O))
Color White
Boiling Point 372.6 °C at 760 mmHg
Assay 98%

4-Chloro-1h-pyrrolo[2,3-b]pyridine-3-carbaldehyde (918515-16-9) Safety and Handling

  • Do not breath dust or vapor.
  • Have safety shower and eye wash available.
  • Do not get in eyes, on skin or on clothing.
  • Keep container tightly closed.
  • Store in a cool, dry, well-ventilated place.
  • Ensure adequate ventilation during use.
  • Use only in a chemical fume hood.

WARNING: The information provided on this web site was developed in compliance with European Union (EU) regulations and is correct to the best of our knowledge, information and belief at the date of its publication. The information given is designed only as a guide for safe handling and use. It is not to be considered as either a warranty or quality specification.

4-Chloro-1h-pyrrolo[2,3-b]pyridine-3-carbaldehyde (918515-16-9) Articles

Discovery of tricyclic dipyrrolopyridine derivatives as novel JAK inhibitors

Janus kinases (JAKs) play a crucial role in cytokine mediated signal transduction. JAK inhibitors have emerged as effective immunomodulative agents for the prevention of transplant rejection.

Bioorganic and Medicinal Chemistry 2017

Synthesis and biological evaluation of pyrrolo[2,3-b]pyridine analogues as antiproliferative agents and their interaction with calf thymus DNA

A series of thirty two novel pyrrolo[2,3-b]pyridine analogues synthesized, characterized (1H NMR, 13C NMR and MS) and cytotoxic evaluation of these molecules carried out over a panel of three human cancer cell lines including A549

European Journal of Medicinal Chemistry 2016

Technical Service:

Our team of scientists has experience in all areas of research including Life Science, Material Science, Chemical Synthesis, Chromatography, Analytical and many others.

 4-Chloro-1h-pyrrolo[2,3-b]pyridine-3-carbaldehyde (918515-16-9) Bulk Ordering & Pricing:

Need larger quantities for your development, manufacturing or research applications?


=

1 review for  4-Chloro-1h-pyrrolo[2,3-b]pyridine-3-carbaldehyde (918515-16-9)

  1. APICMO

    At APICMO, we synthesize and manufacture large amounts of 4-Chloro-1H-pyrrolo[2,3-b]pyridine-3-carbaldehyde, among other chemicals. Our products comply with CGMP manufacturing standards and are majorly for research, development, and production.

    4-Chloro-1h-pyrrolo[2,3-b]pyridine-3-carbaldehyde Description

    JAKs or Janus kinases contribute to the cytokine-mediated signal transduction. Research has confirmed JAK inhibitors to be immunodulative agents, which effectively prevents organ transplant rejections. Initially, tricyclic imidazo-pyrrolopyridine2 was our top JAK inhibitor until we discovered it has a low membrane permeability that weakens oral absorption.

    Structural modification on tricyclic imidazo-pyrrolopyridine 2 reduces the polar surface area, thereby, giving rise to tricyclic imidazo-dipyrrolopyridine. This compound has an improved permeability with an excellent oral absorption, and itexhibits strong vitro activity. When administered in a rat’s cardiac transplant model, it was quite effective.

    (918515-16-9) Product Specifications

    Synonyms · 4-Chloro-7-azaindole-3-carbaldehyde

    · 4-Chloro-3-formyl-7-azaindole

    Structural formula  4-Chloro-1h-pyrrolo[2,3-b]pyridine-3-carbaldehyde(918515-16-9)
    Purity 98% pure
    Physical state Solid
    Monoisotopic mass (g/mol) 180.009
    Molecular weight (g/mol) 180.591
    Molecular formula C8H5ClN2O
    Flash point (˚C) 179.1
    Density (g/cm3) 1.521
    Chemical name 4-Chloro-1H-pyrrolo[2,3-b]pyridine-3-carbaldehyde
    CAS no. 918515-16-9
    Boiling Point (˚C) 372.6 at 760 mmHg

    4-Chloro-1H-pyrrolo[2,3-b]pyridine-3-carbaldehyde

    Chemical and Physical Properties o

    Stability

    4-Chloro-1H-pyrrolo[2,3-b]pyridine-3-carbaldehyde is highly under normal conditions. However, limit exposure of the product to high temperatures, moisture, or strong oxidizing agents as they may trigger decomposition.

    4-Chloro-1H-pyrrolo[2,3-b]pyridine-3-carbaldehyde Bonding

    Hydrogen bond Donor count – 1 unit

    Acceptor counts – 2 units

    Covalent
    Rotatable bond 1

    Appearance

    4-Chloro-1H-pyrrolo[2,3-b]pyridine-3-carbaldehyde is a brown-white solid.

    4-Chloro-1h-pyrrolo[2,3-b]pyridine-3-carbaldehyde (918515-16-9): Computed Properties  

    Property Name Property value
    Complexity 188
    Compound is Canonicalized Yes
    Defined Atom Stereocenter Count 0
    Defined Bond Stereocenter Count 0
    Enthalpy of vaporization (kJ/mol) 61.97
    Exact Mass (g/mol) 180.009
    Formal Charge 0
    Heavy Atom Count 12
    Isotope Atom Count 0
    Polar surface area (PSA) 45.75 Å2
    Refractive index 1.748
    Surface tension (dyne/cm) 71.9
    Topological polar surface area 45.8 A^2
    Undefined Atom Stereocenter Count 0
    Undefined Bond Stereocenter Count 0
    Vapor pressure (mmHg) 9.53E-6
    XLogP3-AA 1.4

    Synthesis Route of 4-Chloro-1H-pyrrolo[2,3-b]pyridine-3-carbaldehyde

    Below are two methods of synthesizing the product:

    Tetrahydro-4-pyranol (2081-44-9)

    4-Chloro-1h-pyrrolo[2,3-b]pyridine-3-carbaldehyde (918515-16-9): Uses

    The product is a pharmaceutical intermediate, serving as JAK inhibitor for preventing organ transplant rejection

    Hazards Associated with 4-Chloro-1H-pyrrolo[2,3-b]pyridine-3-carbaldehyde

    • Harmful when inhaled and might lead to respiratory irritation, shortness of breath, or nausea
    • Causes corrosion, redness, or soreness of the skin when in direct contact
    • Poisonous when swallowed, leading to acute toxicity
    • Eye irritation or permanent damage

    Safety measures when dealing with 4-Chloro-1H-pyrrolo[2,3-b]pyridine-3-carbaldehyde

    1. Personal Protection

    Wear a mask with an air-purifying respirator to prevent accidental inhalations, which would otherwise irritate the respiratory tract.For your hands and feet, put on chemical-resistant gloves and impervious boots, respectively. Wear a full body suit to cover and protect the skin.

    2.  (918515-16-9) :Engineering Controls

    Ensure your working area is equipped with a fume hood, fans, air cleaning devices, safety shower, eyewash, and lockable cabinets.

    3. First Aid Measures

    • Inhalation

    Rinse the mouth for about 10 minutes. Drink plenty of water amounting to half a liter. If symptoms persist, contact a poison center or seek medical attention.

    • Skin contact

    Remove any contaminated clothing immediately. Wash the affected area with enough running water for about 15 minutes. Seek the attention of a medic in case the symptoms persist.

    • Inhalation

    Move the victim to a room with maximum ventilation or outdoor space. If the symptoms become severe such as breathing difficulties, administer oxygen support and consult a medical professional.

    • Eye contact

    Remove contact lenses if you have them on. Flush the eyes with copious amounts of water for the next 10 minutes.

    4. When Using 4-Chloro-1H-pyrrolo[2,3-b]pyridine-3-carbaldehyde

    When the product is in use, consider the points below:

    • Use it in a fume hood
    • Wear protective gears as per the local and state’s occupational safety standards
    • Work in a room with maximum ventilation

    5. After Use

    After using 4-Chloro-1H-pyrrolo[2,3-b]pyridine-3-carbaldehyde, here are some measures to take:

    • Store the remaining chemical under low temperatures
    • Dispose of empty containers and residues appropriately
    • Thoroughly wash your hands
    • Remove the contaminated clothing and wash them before reuse

    6. When out of Use

    When not in use,

    • Lock up the chemical in a tight seal to limit access
    • Keep it refrigerated
    • Avoid exposing it to heat or other chemicals

    7. 4-Chloro-1h-pyrrolo[2,3-b]pyridine-3-carbaldehyde Storage and Handling

    Storage

    • Keep it refrigerated, preferably at -20˚C
    • Store in tightly closed containers
    • Place it in a cool and dry environment
    • Lock up the chemical in sealed cabinets to prevent unauthorized access

    Handling

    • Wear personal protective equipment
    • Use in a chemical fume hood
    • Work in an outdoor space or a well-ventilated room
    • Do not inhale any fumes, gases, dust, or other emissions

    8. Fire Control

    Wear protective clothing and breathing apparatus. Extinguish the flame with foam, carbon dioxide, or chemical dry powder. The combustion products of 4-Chloro-1H-pyrrolo[2,3-b]pyridine-3-carbaldehyde include oxides of nitrogen, HCl, and carbon monoxide.

    9. Managing Spills

    When in a liquid state, mix it with an inert absorbent material, clean up, and dispose of in a labeled and closed container. For a solid state, scoop up the chemical and eliminate it accordingly. Never allow the spillages to find their way through water channels or drains.

    10. Chemical Stability and Reactivity

     

    11. Chemical Disposal

    Handle 4-Chloro-1H-pyrrolo[2,3-b]pyridine-3-carbaldehyde as special waste and dispose of as per the local/state/federal waste disposal regulations. When using the services of a local company, ensure it is registered and licensed.

    12. 4-Chloro-1h-pyrrolo[2,3-b]pyridine-3-carbaldehyde (918515-16-9): Shipping Info

    There are no known hazards with either air or ground transportation of 4-Chloro-1H-pyrrolo[2,3-b]pyridine-3-carbaldehyde.

    Regulatory Info

    The packaging and the threshold level of 4-Chloro-1H-pyrrolo[2,3-b]pyridine-3-carbaldehyde complies with the minimum value stated by SARA Title III sections 302 and 313.

    4-Chloro-1h-pyrrolo[2,3-b]pyridine-3-carbaldehyde:Technical Details

    Our research scientists have maximum experience in material and life sciences, chemical analysis, synthesis, and chromatography.

    4-Chloro-1h-pyrrolo[2,3-b]pyridine-3-carbaldehyde (918515-16-9): Bulk Ordering and Pricing

    If you require 4-Chloro-1H-pyrrolo[2,3-b]pyridine-3-carbaldehyde in bulk,for your research and development,place your order with us by contacting our customer care service.

    Bibliography

    1. National Centre For Biotechnology Information, US. National Library Of Medicine, Pubchem4-Chloro-1h-pyrrolo[2,3-b]pyridine-3-carbaldehyde, Sections 1-10
    2. Naoki Katsuki, Shumpei Isshiki, Juan Okamura, Kouji Kuramochi, , and Kazunori Tsubaki The Journal of Organic Chemistry2017 82 (21), 11563-11572
    3. Ihle JN, Thierfelder W, Teglund S, et al. Signaling by the cytokine receptor superfamily. Ann N Y Acad Sci. 1998;865:1–9

Add a review

Your email address will not be published.