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7-Bromo-2,3-dihydro-1H-pyrido[2,3-b][1,4]oxazine

Name: 7-Bromo-2,3-dihydro-1H-pyrido[2,3-b][1,4]oxazine
Brand: Cuicheng Bio
SKU: pr2606011653
Price: 200 USD
Availability: InStock

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CAS No.:

946121-78-4

Grade:

Industrial Grade

Content:

97%

Port:

guangzhou

Brand:

Cuicheng Bio

Packaging:

g/kg

Price valid (until):

2027-03-04

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Cuicheng Biomedical Technology

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Manufactory

Location:

China

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Main Products:

Ginsenoside Rb1,Ginsenoside Rg1,Ginsenoside Re,Ginsenoside CK,Ginsenoside Rg2,Ginsenoside Rg5

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Description
7-Bromo-2,3-dihydro-1H-pyrido[2,3-b][1,4]oxazine (CAS No.: 946121-78-4) is a highly specific fused bicyclic small molecule primarily used as a fine chemical scaffold and synthetic intermediate in medicinal chemistry.

Compared to its carbonyl analog discussed earlier (the 2-one oxidized state), this structure has been reduced to a 2,3-dihydro form, which significantly alters its physical, chemical, and pharmacodynamic properties.

1. Physical and Structural Properties

Molecular Basis: The chemical formula is $\text{C}_7\text{H}_7\text{BrN}_2\text{O}$, with a molecular weight of 215.05.

Appearance: It typically appears as a solid or crystalline powder at room temperature and standard atmospheric pressure.

Predicted Density: Approximately $1.619\pm 0.06\text{ g/cm}^3$ (the removal of the carbonyl group results in a lower density compared to the 2-one analog).

Predicted Boiling Point: Approximately $312.4\pm 42.0\text{ }^\circ\text{C}$ at standard atmospheric pressure.

Topology and Spatial Conformation: The removal of the 2-position ketone ($\text{C}=\text{O}$) slightly reduces the rigidity of the entire fused ring system, which typically increases the molecule's lipophilicity ($\text{logP}$) and cell membrane permeability.

2. Chemical Reactivity (Versatile Modification Sites)

Due to its unique pyrido-oxazine saturated ring structure, the compound possesses highly distinct and independent late-stage modification vectors:

The N-1 Position (Secondary Aliphatic Amine Reactivity): The 1-position acts as a typical secondary amine, which exhibits much higher nucleophilicity than the previous amide nitrogen. It easily undergoes sulfonylation, alkylation, or acylation reactions. For instance, in the presence of pyridine, it reacts efficiently with arylsulfonyl chlorides to generate sulfonamide derivatives with excellent targeting activities.

The C-7 Position (Transition-Metal-Catalyzed Coupling): The bromine atom on the pyridine ring serves as a strong leaving group, allowing it to undergo Suzuki-Miyaura cross-coupling reactions or Miura borylation. This enables chemists to introduce complex heterocycles, such as pyrimidines, at this specific vector for constructing multi-target drugs.

The Oxazine Ring (Structural Stability): The fused saturated oxazine ring provides a specific spatial conformation, ensuring that the molecule maintains an optimal geometric orientation when entering the pocket of a target protein.

3. Biomedical Applications

In cutting-edge targeted anticancer drug design, this compound serves as a critical "privileged fragment":

Next-Generation EGFR Inhibitors: Recent pharmacological studies leverage this substance as a core scaffold, systematically conjugating it with pyrimidine and sulfonamide pharmacophores to develop novel EGFR-TK inhibitors for non-small cell lung cancer (NSCLC).

Overcoming Mutational Resistance: Derivatives developed from this scaffold demonstrate significant in vitro inhibitory activity against drug-resistant lung cancer cells harboring the L858R/T790M double mutation (e.g., H1975). They efficiently induce apoptosis in cancer cells while showing minimal toxicity to normal cells.
Items Specifications
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Product Name:
7-Bromo-2,3-dihydro-1H-pyrido[2,3-B][1,4]oxazine

CAS No.:
946121-78-4

Categories:
Organic Reagents
Seller Information

Business Type:
Manufactory

Main Products:
Ginsenoside Rb1,Ginsenoside Rg1,Ginsenoside Re,Ginsenoside CK,Ginsenoside Rg2,Ginsenoside Rg5

Location:
Chuangzhi valley,Chuangzhi Industrial Park ,Hanzhong Economic and Technological Dvelopment Zone,Hanzhong City, Shaanxi Province

Year of Establishment:
2019
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Items	Specifications

7-Bromo-2,3-dihydro-1H-pyrido[2,3-b][1,4]oxazine

Product Description

Seller Information

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