5,6,7,8-Tetrahydroimidazo[1,2-a]pyridine

Base Information

• Chemical Name: 5,6,7,8-Tetrahydroimidazo[1,2-a]pyridine
• CAS No.: 34167-66-3
• Molecular Formula: C7H10N2
• Molecular Weight: 122.17
• Hs Code.: 2933990090
• European Community (EC) Number: 817-387-4
• DSSTox Substance ID: DTXSID10433668
• Nikkaji Number: J603.915D
• Wikidata: Q82247869
• ChEMBL ID: CHEMBL4537948
• Mol file: 34167-66-3.mol

Synonyms:5,6,7,8-Tetrahydroimidazo[1,2-a]pyridine;34167-66-3;5,6,7,8-tetrahydro-imidazo[1,2-a]pyridine;5H,6H,7H,8H-imidazo[1,2-a]pyridine;MFCD11849324;Imidazo[1,2-a]pyridine, 5,6,7,8-tetrahydro- (8CI,9CI);Imidazo[1,2-a]pyridine,5,6,7,8-tetrahydro-;SCHEMBL238844;CHEMBL4537948;DTXSID10433668;PPRGXYWEHFENBY-UHFFFAOYSA-N;BBL103732;STL557542;AKOS015907627;AB64837;AM90258;AC-22766;AS-76252;SY192800;CS-0138089;FT-0646135;EN300-96318;A23058;D78690;IMIDAZO[1,2-A]PYRIDINE, 5,6,7,8-TETRAHYDRO-;Z1255462261

Chemical Property of 5,6,7,8-Tetrahydroimidazo[1,2-a]pyridine

Chemical Property:

• Vapor Pressure: 0.005mmHg at 25°C
• Refractive Index: 1.628
• Boiling Point: 284.716 °C at 760 mmHg
• PKA: 7.75±0.20(Predicted)
• Flash Point: 125.992 °C
• PSA: 17.82000
• Density: 1.181 g/cm³
• LogP: 1.21940
• XLogP3: 0.7
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 1
• Rotatable Bond Count: 0
• Exact Mass: 122.084398327
• Heavy Atom Count: 9
• Complexity: 103

Purity/Quality:

99%, ^*data from raw suppliers

5,6,7,8-tetrahydroimidazo[1,2-a]pyridine ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1CCN2C=CN=C2C1
• General Description: 5,6,7,8-Tetrahydroimidazo[1,2-a]pyridine derivatives, such as compound **8**, exhibit strong DNA binding affinity and potent in vitro antiprotozoal activity, particularly against *Trypanosoma brucei rhodesiense* (IC50 values of 7–38 nM). These compounds demonstrate potential as antiprotozoal agents, with some derivatives outperforming furamidine in efficacy. However, their activity against *Plasmodium falciparum* is comparatively weaker (IC50 values of 23–92 nM). The structural modifications, including linker choice and saturation of the imidazo[1,2-a]pyridine core, influence their biological performance.

Technology Process of 5,6,7,8-Tetrahydroimidazo[1,2-a]pyridine

There total 11 articles about 5,6,7,8-Tetrahydroimidazo[1,2-a]pyridine 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: 97.0%

2-(4-chlorobutyl)imidazole (137415-92-0) → 5,6,7,8-TETRAHYDROIMIDAZO[1,2-A]PYRIDINE (34167-66-3)

Guidance literature:

With sodium iodide; In methanol; for 6h; Heating;

DOI:10.1016/j.tet.2006.12.003

Reference yield: 85.9%

5-chloro-N-(2,2-dimethoxyethyl)pentanimidamide → 5,6,7,8-TETRAHYDROIMIDAZO[1,2-A]PYRIDINE (34167-66-3)

Guidance literature:

With formic acid; at 100 ℃; for 6h;

Reference yield: 85.0%

5-(2,2-dimethoxy-ethylamino)-pentanenitrile → 5,6,7,8-TETRAHYDROIMIDAZO[1,2-A]PYRIDINE (34167-66-3)

Guidance literature:

With trifluoroacetic acid; at 75 ℃; for 1h;

DOI:10.1016/j.tetlet.2005.09.153

upstream raw materials:

piperidin-2-one

2,2-diethoxy-ethanamine

2-(4-chlorobutyl)imidazole

1-<4-(phenylselanyl)butyl>-2-tosyl-1H-imidazole

Downstream raw materials:

3-bromo-5,6,7,8-tetrahydroimidazo[1,2-a]pyridine

Refernces

Synthesis and antiprotozoal activity of novel bis-benzamidino imidazo[1,2-a]pyridines and 5,6,7,8-tetrahydro-imidazo[1,2-a]pyridines

10.1016/j.bmc.2007.10.042

The research focuses on the synthesis and evaluation of novel bis-benzamidino imidazo[1,2-a]pyridines and 5,6,7,8-tetrahydroimidazo[1,2-a]pyridines for their antiprotozoal activity and DNA binding affinity. The key dinitrile intermediates 4a–d were synthesized by reacting phenacyl bromide 1 with appropriate 2-amino-5-bromopyridines to yield 3a–d, followed by Suzuki coupling with 4-cyanophenylboronic acid. The bis-amidoximes 5a–d were then converted to the bis-O-acetoxyamidoximes and further catalytically hydrogenated to yield the acetate salts of 2,6-bis[4-(amidinophenyl)]-imidazo[1,2-a]pyridines 7a–d and the saturated analogue 2,6-bis[4-(amidinophenyl)]-5,6,7,8-tetrahydro-imidazo[1,2-a]pyridine 8. The N-methoxyamidines 6a–d were prepared as potential prodrugs. These compounds exhibited strong DNA binding affinity and were very active in vitro against Trypanosoma brucei rhodesiense (T. b. r.), with IC50 values between 7 and 38 nM, but less effective against Plasmodium falciparum (P. f.), with IC50 values between 23 and 92 nM. In the T. b. r. STIB900 mouse model, compounds 7c and 7d showed slightly higher activity than furamidine, while only one prodrug 6b exhibited moderate activity. The research highlights the potential of these compounds as antiprotozoal agents and demonstrates the importance of the choice of linker and solvent in the synthesis and activity of these compounds.

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