135631-90-2

Basic information

• Product Name: 6-BROMO-3,4-DIHYDRO-4,4-DIMETHYLQUINOLIN-2(1H)-ONE
• Synonyms: 6-BROMO-3,4-DIHYDRO-4,4-DIMETHYLQUINOLIN-2(1H)-ONE;4-dihydro-4;4-diMethylquinolin-2(1H)-one;6-Bromo-4,4-dimethyl-3,4-dihydro-1H-quinolin-2-one
• CAS NO: 135631-90-2
• Molecular Formula: C₁₁H₁₂BrNO
• Molecular Weight: 254.12
• Product Categories: CHIRAL CHEMICALS
• Mol File: 135631-90-2.mol

Chemical Properties

• Boiling Point: 366.03 °C at 760 mmHg
• Flash Point: 175.169 °C
• Appearance: /
• Density: 1.386 g/cm³
• Vapor Pressure: 0mmHg at 25°C
• Refractive Index: 1.556
• Storage Temp.: Room temperature.
• CAS DataBase Reference: 6-BROMO-3,4-DIHYDRO-4,4-DIMETHYLQUINOLIN-2(1H)-ONE(CAS DataBase Reference)
• NIST Chemistry Reference: 6-BROMO-3,4-DIHYDRO-4,4-DIMETHYLQUINOLIN-2(1H)-ONE(135631-90-2)
• EPA Substance Registry System: 6-BROMO-3,4-DIHYDRO-4,4-DIMETHYLQUINOLIN-2(1H)-ONE(135631-90-2)

Safety Data

• Hazardous Substances Data: 135631-90-2(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Research and Drug Development:
6-Bromo-3,4-dihydro-4,4-dimethylquinolin-2(1H)-one is utilized as a key component in pharmaceutical research and drug development due to its demonstrated antibacterial, antifungal, and antitumor properties. Its multifaceted biological activities make it a promising candidate for the creation of new therapeutic agents.
Used in Organic Synthesis:
In the field of organic synthesis, 6-Bromo-3,4-dihydro-4,4-dimethylquinolin-2(1H)-one is employed as a starting material for the synthesis of various biologically active compounds. Its unique structure allows for the development of a range of derivatives with potential applications in medicine and other industries.
Used in Antimicrobial Applications:
6-Bromo-3,4-dihydro-4,4-dimethylquinolin-2(1H)-one is used as an antimicrobial agent for its ability to combat bacterial and fungal infections. Its effectiveness in this application is attributed to its capacity to interfere with essential cellular processes in microorganisms, thereby inhibiting their growth and proliferation.
Used in Antitumor Applications:
In the context of antitumor applications, 6-Bromo-3,4-dihydro-4,4-dimethylquinolin-2(1H)-one is leveraged for its potential to inhibit tumor growth. Its mechanism of action may involve the disruption of cellular pathways that contribute to the development and progression of cancer, offering a valuable tool in oncology research.
Used in the Synthesis of Biologically Active Compounds:
6-Bromo-3,4-dihydro-4,4-dimethylquinolin-2(1H)-one is used as a precursor in the synthesis of a variety of biologically active compounds. Its structural features facilitate the creation of new molecules with potential therapeutic benefits, expanding the scope of available treatments for various diseases and conditions.

InChI:InChI=1/C11H12BrNO/c1-11(2)6-10(14)13-9-4-3-7(12)5-8(9)11/h3-5H,6H2,1-2H3,(H,13,14)

Upstream product

• 106-40-1 4-bromo-aniline 
• 3350-78-5 3,3-Dimethylacryloyl chloride 
• 1176219-38-7 N-(4-bromophenyl)-3-methylbut-3-enamide 
• 135631-89-9 N-(3,3'-dimethylacryoloyl)-4-bromoaniline 

Downstream Products

• 1187933-54-5 tert-butyl 6-amino-4,4-dimethyl-3,4-dihydroquinoline-1(2H)-carboxylate 
• 263550-60-3 tert-butyl 6-bromo-4,4-dimethyl-3,4-dihydroquinoline-1(2H)-carboxylate 
• 1353043-43-2 methyl 3-[4-(6-bromo-4,4-dimethyl-2-oxo-3,4-dihydro-2H-quinolin-1-ylmethoxy)phenyl]hex-4-ynoate 
• 1353043-04-5 3-[4-(6-bromo-4,4-dimethyl-2-oxo-3,4-dihydro-2H-quinolin-1-ylmethoxy)phenyl]hex-4-ynoic acid 
• 304858-26-2 3-(4,4-dimethyl-2-oxo-1,2,3,4-tetrahydroquinolin-6-yl)benzonitrile 
• 304857-67-8 6-(3-chlorophenyl)-4,4-dimethyl-3,4-dihydro-1H-quinolin-2-one 
• 304858-53-5 6-bromo-1-(4-methoxy-benzyl)-4,4-dimethyl-3,4-dihydro-1H-quinolin-2-one 
• 198696-06-9 4-(1-Heptyl-4,4-dimethyl-1,2,3,4-tetrahydro-quinolin-6-ylethynyl)-benzoic acid ethyl ester 
• 185316-16-9 4-(1-Isopropyl-4,4-dimethyl-2-oxo-1,2,3,4-tetrahydro-quinolin-6-ylethynyl)-benzoic acid ethyl ester 

Relevant articles and documents

Inhibitors Targeting STAT5 Signaling in Myeloid Leukemias: New Tetrahydroquinoline Derivatives with Improved Antileukemic Potential

Signal transducers and activators of transcription 5A and 5B (STAT5A and STAT5B) are two closely related STAT family members that are crucial downstream effectors of tyrosine kinase oncoproteins such as FLT3-ITD in acute myeloid leukemia (AML) and BCR-ABL

Tetrahydroquinoline units in flexible heteroarotinoids (Flex-Hets) convey anti-cancer properties in A2780 ovarian cancer cells

SHetA2 (NSC 721689), our lead Flex-Het anti-cancer agent, consists of a thiochroman (Ring A) and a 4-nitrophenyl (Ring B) linked by a thiourea bridge. In this work, several series of new analogs having a tetrahydroquinoline (THQ, Ring A) unit connected by

CHROMAN-SUBSTITUTED, TETRAHYDROQUINOLINE-SUBSTITUTED AND THIOCHROMAN-SUBSTITUTED HETEROAROTINOIDS AS ANTI-CANCER AGENTS

Chemical compounds that inhibit cancer cell growth are provided. The compounds are heteroarotinoids and derivatives thereof with oxygen, nitrogen or sulfur in chroman systems, tetrahydroquinoline systems, and tetrahydrothiochroman systems.

New Inhibitor Targeting Signal Transducer and Activator of Transcription 5 (STAT5) Signaling in Myeloid Leukemias

Signal transducers and activators of transcription 5 (STAT5s) are crucial effectors of tyrosine kinase oncogenes in myeloid leukemias. Inhibition of STAT5 would contribute to reducing the survival of leukemic cells and also tackling their chemoresistance. In a first screening experiment, we identified hit 13 as able to inhibit STAT5 phosphorylation and leukemic cell growth. The synthesis of 18 analogues of 13 allowed us to identify one compound, 17f, as having the most potent antileukemic effect. 17f inhibited the growth of acute and chronic myeloid leukemia cells and the phosphorylation and transcriptional activity of STAT5. Importantly, 17f had minimal effects on bone marrow stromal cells that play vital functions in the microenvironment of hematopoietic and leukemic cells. We also demonstrated that 17f inhibits STAT5 but not STAT3, AKT, or Erk1/2 phosphorylation. These results suggest that 17f might be a new lead molecule targeting STAT5 signaling in myeloid leukemias.

Practical synthetic strategies towards lipophilic 6-iodotetrahydroquinolines and -dihydroquinolines

The synthesis of novel tetrahydroquinolines (THQ) and dihydroquinolines (DHQ) are reported using three practical, scalable synthetic approaches to access highly lipophilic analogues bearing a 6-iodo substituent, each with a different means of cyclisation. A versatile and stable quinolin-2-one intermediate was identified, which could be reduced to the corresponding THQ with borane reagents, or to the DHQ with diisobutylaluminium hydride via a novel elimination that is more favourable at higher temperatures. Coupling these strongly electron-donating scaffolds to electron-accepting moieties caused the resulting structures to exhibit strong fluorescence.

SUBSTITUTED BENZO[d][1,3]OXAZIN-2(4H)-ONES AND RELATED DERIVATIVES AND THEIR USES FOR MODULATING THE PROGESTERONE RECEPTOR

Compounds of formula (I), or pharmaceutically acceptable salts thereof, are provided, wherein R1-R6 and X are defined herein. Also provided are methods of preparing the compounds of formula (I), pharmaceutical compositions and kits containing a compound of formula (I), as are methods of treating endometriosis, hormone-dependent carcinomas, leiomyoma, fibroids, dysfunctional bleeding, polycystic ovary syndrome, and menopause related symptoms; methods of contraception; methods of providing hormone replacement therapy; methods of stimulating food intake; methods of synchronizing estrus; and methods of treating symptoms of premenstrual syndrome and premenstrual dysphoric disorder by administering to a mammal in need thereof a pharmaceutically effective amount of a compound of formula (I).

Disubstituted chalcone oximes as selective agonists of RAR retinoid receptors

Compounds of the formula where the variables are as defined in the specification, are useful for preventing or treating emphysema and related pulmonary conditions of mammals and other diseases and conditions which are responsive to RARγ agonist retinoids, such as skin related diseases, including but not limited to acne and psoriasis.

5-[PHENYL-TETRAHYDRONAPHTHALENE-2-YL DIHYDRONAPHTHALEN-2-YL AND HETEROARYL-CYCLOPROPYL]-PENTADIENOIC ACID DERIVATIVES HAVING SERUM GLUCOSE REDUCING ACTIVITY

Compounds of the formula where the variables have the meaning defined in the specification are capable of reducing serum glucose levels in diabetic mammals without the undesirable side effects of reducing serum thyroxine levels and transiently increasing triglyceride levels.

[3-(C5-14ALKYL-2-OXO-1,2,3,4-TETRAHYDRO-QUINOLIN-6-YL)-3-OXO-PROPENYL]-PHENYL AND [3-(C5-14ALKYL-2-OXO-1,2,3,4- TETRAHYDRO-QUINOLIN-6-YL)-3-OXO-PROPENYL]-HETEROARYL DERIVATIVES HAVING ANTI-TUMOR ACTIVITY

Compounds of the formula where the variables have the meaning defined in the specification have anti-tumor activity.

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.