304858-44-4

Basic information

• Product Name: 6-BROMO-2,4,4-TRIMETHYL-2,4-DIHYDRO-1H-BENZO[D][1,3]OXAZINE
• Synonyms: 6-BROMO-2,4,4-TRIMETHYL-2,4-DIHYDRO-1H-BENZO[D][1,3]OXAZINE
• CAS NO: 304858-44-4
• Molecular Formula: C₁₁H₁₄BrNO
• Molecular Weight: 256.14
• Mol File: 304858-44-4.mol

Chemical Properties

• Boiling Point: 326.9±42.0 °C(Predicted)
• Appearance: /
• Density: 1.294±0.06 g/cm3(Predicted)
• PKA: 2.37±0.60(Predicted)
• CAS DataBase Reference: 6-BROMO-2,4,4-TRIMETHYL-2,4-DIHYDRO-1H-BENZO[D][1,3]OXAZINE(CAS DataBase Reference)
• NIST Chemistry Reference: 6-BROMO-2,4,4-TRIMETHYL-2,4-DIHYDRO-1H-BENZO[D][1,3]OXAZINE(304858-44-4)
• EPA Substance Registry System: 6-BROMO-2,4,4-TRIMETHYL-2,4-DIHYDRO-1H-BENZO[D][1,3]OXAZINE(304858-44-4)

Safety Data

• Hazardous Substances Data: 304858-44-4(Hazardous Substances Data)

Upstream product

• 304853-89-2 2-(2-amino-5-bromophenyl)-propan-2-ol 
• 29124-56-9 1-(2-amino-5-bromophenyl)ethanone 
• 75-07-0 acetaldehyde 

Downstream Products

• 304857-74-7 4-(2,4,4-Trimethyl-1,4-dihydro-2H-3,1-benzoxazin-6-yl)thiophene-2-carbonitrile 

Relevant articles and documents

Cyclic regimens using quinazolinone and benzoxazine derivatives

This invention relates to cyclic combination therapies utilizing, in combination with progestins, estrogens, or both, compounds which are progesterone receptor antagonists of the general structure: wherein: R1and R2are H, CORA, or NRBCORA, alkyl, alkenyl, alkynyl, cycloalkyl, aryl, or heterocyclic; or R1and R2fuse to form 3 to 8 membered spirocyclic alkyl, alkenyl or heterocyclic rings; RAis H or optionally substituted alkyl, aryl, alkoxy, or aminoalkyl groups; RBis H or alkyl; R3is H, OH, NH2, CORCor alkyl, alkenyl, or alkynyl; RCis H, alkyl, aryl, alkoxy, or aminoalkyl; R4is H, halogen, CN, NO2, alkyl, alkynyl, alkoxy, amino or aminoalkyl; R5is benzene or 5- or 6-membered heterocyclic ring; R6is H or alkyl; G1is O, NR7, or CR7R8; G2is CO or CR7R8; provided that when G1is O, G2is CR7R8, and G1and G2cannot both be CR7R8; R7and R8are H or an optionally substituted alkyl, aryl, or heterocyclic moiety; or pharmaceutically acceptable salt thereof. These methods may be used for contraception or treatment and/or prevention of secondary amenorrhea, dysfunctional bleeding, uterine leiomyomata, endometriosis; polycystic ovary syndrome, carcinomas and adenocarcinomas of the endometrium, ovary, breast, colon, prostate, or minimization of side effects or cyclic menstrual bleeding. Additional uses of the invention include stimulation of food intake.

Potent nonsteroidal progesterone receptor agonists: Synthesis and SAR study of 6-aryl benzoxazines

Novel 6-aryl benzoxazines were prepared and examined as progesterone receptor (PR) modulators. In contrast to the structurally related 6-aryl dihydroquinoline PR antagonists, the 6-aryl benzoxazines were potent PR agonists. Compounds 4e, 5b, and 6a with the 2,4,4-trimethyl-1,4-dihydro-2H-benzo[d][1,3]oxazine core were the most potent PR agonists in the series with sub-nanomolar activities (EC50 0.20-0.35 nM). Compound 6a was more potent than progesterone (P4) in the in vivo decidualization assay in an ovariectomized female rat model by subcutaneous administration with an ED50 of 1.5 mg/kg (vs 5.62 mg/kg for P4).

Quinazolinone and benzoxazine derivatives as progesterone receptor modulators

This invention provides compounds which are agonists and antagonists of the progesterone receptor having the general structure: wherein: R1and R2are independently selected from H, CORA, or NRBCORA, or optionally substituted alkyl, alkenyl, alknyl, cycloalklyl, aryl, or heterocyclic moieties; or R1and R2are fused to form: 3 to 8 membered spirocyclic alkyl, alkenyl or heterocyclic rings; RAis H or optionally substituted alkyl, aryl, alkoxy, or aminoalkyl groups; RBis H, C1to C3alkyl, or substituted C1to C3alkyl; R3is H, OH, NH2, CORCor optionally substituted alkyl, alkenyl, or alkynyl; RCis H or optionally substituted alkyl, aryl, alkoxy, or aminoalkyl; R4is H, halogen, CN, NO2, or optionally substituted alkyl, alkynyl, alkoxy, amino or aminoalkyl; R5is an optionally substituted benzene or five or six membered ring with 1, 2, or 3 heteroatoms selected from O, S, SO, SO2or NR6; R6is H or C1to C3alkyl; G1is O, NR7, or CR7R8; G2is CO, CS, or CR7R8; provided that when G1is O, G2is CR7R8, and G1and G2cannot both be CR7R8; R7and R8are H or an optionally substituted alkyl, aryl, or heterocyclic moiety; or pharmaceutically acceptable salt thereof, and methods using these compounds in mammals as agonists or antagonists of the progesterone receptor.