1H-pyrazolo[3,4-b]quinolin-3-amine

Base Information

• Chemical Name: 1H-pyrazolo[3,4-b]quinolin-3-amine
• CAS No.: 106835-44-3
• Molecular Formula: C10H8N4
• Molecular Weight: 184.19700
• Hs Code.: 2933990090
• European Community (EC) Number: 830-246-1
• DSSTox Substance ID: DTXSID40349869
• Nikkaji Number: J1.561.962G
• Wikidata: Q82125399
• ChEMBL ID: CHEMBL1369953
• Mol file: 106835-44-3.mol

Synonyms:1H-pyrazolo[3,4-b]quinolin-3-amine;106835-44-3;2H-pyrazolo[3,4-b]quinolin-3-amine;MFCD00895693;3-amino-1h-pyrazolo[3,4-b]quinoline;MLS000729424;CHEMBL1369953;SCHEMBL10333619;DTXSID40349869;KEVOFPICRVTBPL-UHFFFAOYSA-N;HMS2727C17;NSC777499;STK726460;AKOS001752106;NSC-777499;NS-01645;SMR000307702;EN300-60237;Z57164775

Chemical Property of 1H-pyrazolo[3,4-b]quinolin-3-amine

Chemical Property:

• PSA: 68.32000
• LogP: 1.62340
• XLogP3: 1.8
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 0
• Exact Mass: 184.074896272
• Heavy Atom Count: 14
• Complexity: 220

Purity/Quality:

99% ^*data from raw suppliers

1H-Pyrazolo[3,4-b]quinolin-3-amine ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

• Canonical SMILES: C1=CC2=CC3=C(NN=C3N=C2C=C1)N

Technology Process of 1H-pyrazolo[3,4-b]quinolin-3-amine

There total 9 articles about 1H-pyrazolo[3,4-b]quinolin-3-amine which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 92.0%

2-chloroquinoline-3-carbonitrile (95104-21-5) → 1H‐pyrazolo[3,4‐b]quinolin‐3‐amine (106835-44-3)

Guidance literature:

With hydrazine hydrate; In ethanol; for 3h; Heating;

DOI:10.1002/jccs.200100173

Reference yield:

2-chloro-3-quinoline carboxaldehyde (73568-25-9) → 1H‐pyrazolo[3,4‐b]quinolin‐3‐amine (106835-44-3)

Guidance literature:

Multi-step reaction with 2 steps

1: 86 percent / aq. ammonia; cerium(IV) ammonium nitrate / 0 °C

2: 92 percent / hydrazine hydrate / 0.25 h / Heating

With ammonium hydroxide; ammonium cerium(IV) nitrate; hydrazine hydrate;

Reference yield:

Acetanilid (103-84-4) → 1H‐pyrazolo[3,4‐b]quinolin‐3‐amine (106835-44-3)

Guidance literature:

Multi-step reaction with 3 steps

1: 82 percent / POCl₃ / 80 - 90 °C

2: 86 percent / aq. ammonia; cerium(IV) ammonium nitrate / 0 °C

3: 92 percent / hydrazine hydrate / 0.25 h / Heating

With ammonium hydroxide; ammonium cerium(IV) nitrate; hydrazine hydrate; trichlorophosphate;

upstream raw materials:

2-chloroquinoline-3-carbonitrile

2-chloro-3-quinoline carboxaldehyde

Acetanilid

2-oxo-1,2-dihydroquinoline-3-carbonitrile

Downstream raw materials:

[1-(4-Bromo-phenyl)-meth-(E)-ylidene]-(1H-pyrazolo[3,4-b]quinolin-3-yl)-amine

3-benzoylamino-4-aminoquinolino[2',3'-5,4](3-1H-pyrazolino)[2,3-a]pyrimidin-2-one

3-phenyl-1-(1H-pyrazolo[3,4-b]quinolin-3-yl)thiourea

3-benzylideneamino-1H-pyrazolo[3,4-b]quinoline

Refernces

• 1、 Cui, Xiuling,Han, Xiliang,Hu, Di,Hu, Wei,Pi, Chao,Wu, Yangjie. "Ru(III)-catalyzed construction of variously substituted quinolines from 2-aminoaromatic aldehydes (ketones) and isoxazoles: Isoxazoles as cyclization reagent and cyano sources". supporting information. . Retrieved 2022/01/28.
• 2、 Karthikeyan, Chandrabose,Amawi, Haneen,Viana, Arabela Guedes,Sanglard, Leticia,Hussein, Noor,Saddler, Maria,Ashby, Charles R.,Moorthy, N.S. Hari Narayana,Trivedi, Piyush,Tiwari, Amit K.. "lH-Pyrazolo[3,4-b]quinolin-3-amine derivatives inhibit growth of colon cancer cells via apoptosis and sub G1 cell cycle arrest". . p. 2244 - 2249. Retrieved 2018/05/31.