BIOMAT Database Logo BIOMAT Database Logo

Nanomolar potency of imidazo[2,1-b]thiazole analogs as indoleamine 2,3-dioxygenase inhibitors. 2021

Menna A Ewida, and Heba A Ewida, and Mahmoud S Ahmed, and Heba Abdelrasheed Allam, and Ramzia I ElBagary, and Riham F George, and Hanan H Georgey, and Hussein I El-Subbagh
Department of Pharmaceutical Chemistry, Faculty of Pharmaceutical Sciences & Pharmaceutical Industries, Future University in Egypt, Cairo, Egypt.

Novel series of imidazo[2,1-b]thiazole analogs were designed, synthesized, and biologically evaluated as indoleamine 2,3-dioxygenase (IDO1) inhibitors. Imidazo[2,1-b]thiazoles 6, 7, and 8 showed inhibitory profiles against IDO1 at IC50 values of 68.48, 82.39, and 48.48 nM, respectively, compared with IDO5L at IC50 67.40 nM. Benzo[d]imidazo[2,1-b]thiazoles 17, 20, and 22 showed promising IDO1 inhibition at IC50 values of 53.58, 53.16, and 57.95 nM, respectively. Compound 7 showed a growth-inhibitory profile at GI of 39.33% against the MCF7 breast cancer cell line, while 8 proved lethal to ACHN renal cancer cells. Cells treated with compounds 17 and 22 showed a typical apoptosis pattern of DNA fragments that reflected the G0/G1, S, and G2/M phases of the cell cycle, together with a pre-G1 phase corresponding to apoptotic cells, which indicates that cell growth arrest occurred at the S phase. Molecular modeling simulations validated the potential of benzo[d]imidazo[2,1-b]thiazole analogs to chelate iron(III) within the IDO1 binding pocket and, hence, to have a better binding affinity via hydrophobic-hydrophobic interactions.

UI MeSH Term Description Entries
D007093 Imidazoles Compounds containing 1,3-diazole, a five membered aromatic ring containing two nitrogen atoms separated by one of the carbons. Chemically reduced ones include IMIDAZOLINES and IMIDAZOLIDINES. Distinguish from 1,2-diazole (PYRAZOLES).
D007680 Kidney Neoplasms Tumors or cancers of the KIDNEY. Cancer of Kidney,Kidney Cancer,Renal Cancer,Cancer of the Kidney,Neoplasms, Kidney,Renal Neoplasms,Cancer, Kidney,Cancer, Renal,Cancers, Kidney,Cancers, Renal,Kidney Cancers,Kidney Neoplasm,Neoplasm, Kidney,Neoplasm, Renal,Neoplasms, Renal,Renal Cancers,Renal Neoplasm
D008958 Models, Molecular Models used experimentally or theoretically to study molecular shape, electronic properties, or interactions; includes analogous molecules, computer-generated graphics, and mechanical structures. Molecular Models,Model, Molecular,Molecular Model
D001943 Breast Neoplasms Tumors or cancer of the human BREAST. Breast Cancer,Breast Tumors,Cancer of Breast,Breast Carcinoma,Cancer of the Breast,Human Mammary Carcinoma,Malignant Neoplasm of Breast,Malignant Tumor of Breast,Mammary Cancer,Mammary Carcinoma, Human,Mammary Neoplasm, Human,Mammary Neoplasms, Human,Neoplasms, Breast,Tumors, Breast,Breast Carcinomas,Breast Malignant Neoplasm,Breast Malignant Neoplasms,Breast Malignant Tumor,Breast Malignant Tumors,Breast Neoplasm,Breast Tumor,Cancer, Breast,Cancer, Mammary,Cancers, Mammary,Carcinoma, Breast,Carcinoma, Human Mammary,Carcinomas, Breast,Carcinomas, Human Mammary,Human Mammary Carcinomas,Human Mammary Neoplasm,Human Mammary Neoplasms,Mammary Cancers,Mammary Carcinomas, Human,Neoplasm, Breast,Neoplasm, Human Mammary,Neoplasms, Human Mammary,Tumor, Breast
D002453 Cell Cycle The complex series of phenomena, occurring between the end of one CELL DIVISION and the end of the next, by which cellular material is duplicated and then divided between two daughter cells. The cell cycle includes INTERPHASE, which includes G0 PHASE; G1 PHASE; S PHASE; and G2 PHASE, and CELL DIVISION PHASE. Cell Division Cycle,Cell Cycles,Cell Division Cycles,Cycle, Cell,Cycle, Cell Division,Cycles, Cell,Cycles, Cell Division,Division Cycle, Cell,Division Cycles, Cell
D005260 Female Females
D006801 Humans Members of the species Homo sapiens. Homo sapiens,Man (Taxonomy),Human,Man, Modern,Modern Man
D000970 Antineoplastic Agents Substances that inhibit or prevent the proliferation of NEOPLASMS. Anticancer Agent,Antineoplastic,Antineoplastic Agent,Antineoplastic Drug,Antitumor Agent,Antitumor Drug,Cancer Chemotherapy Agent,Cancer Chemotherapy Drug,Anticancer Agents,Antineoplastic Drugs,Antineoplastics,Antitumor Agents,Antitumor Drugs,Cancer Chemotherapy Agents,Cancer Chemotherapy Drugs,Chemotherapeutic Anticancer Agents,Chemotherapeutic Anticancer Drug,Agent, Anticancer,Agent, Antineoplastic,Agent, Antitumor,Agent, Cancer Chemotherapy,Agents, Anticancer,Agents, Antineoplastic,Agents, Antitumor,Agents, Cancer Chemotherapy,Agents, Chemotherapeutic Anticancer,Chemotherapy Agent, Cancer,Chemotherapy Agents, Cancer,Chemotherapy Drug, Cancer,Chemotherapy Drugs, Cancer,Drug, Antineoplastic,Drug, Antitumor,Drug, Cancer Chemotherapy,Drug, Chemotherapeutic Anticancer,Drugs, Antineoplastic,Drugs, Antitumor,Drugs, Cancer Chemotherapy
D013329 Structure-Activity Relationship The relationship between the chemical structure of a compound and its biological or pharmacological activity. Compounds are often classed together because they have structural characteristics in common including shape, size, stereochemical arrangement, and distribution of functional groups. Relationship, Structure-Activity,Relationships, Structure-Activity,Structure Activity Relationship,Structure-Activity Relationships
D013844 Thiazoles Heterocyclic compounds where the ring system is composed of three CARBON atoms, a SULFUR and NITROGEN atoms. Thiazole

Related Publications

Menna A Ewida, and Heba A Ewida, and Mahmoud S Ahmed, and Heba Abdelrasheed Allam, and Ramzia I ElBagary, and Riham F George, and Hanan H Georgey, and Hussein I El-Subbagh
Imidazo[2,1-b]thiazole guanylhydrazones as RSK2 inhibitors.
September 2011, European journal of medicinal chemistry,
Menna A Ewida, and Heba A Ewida, and Mahmoud S Ahmed, and Heba Abdelrasheed Allam, and Ramzia I ElBagary, and Riham F George, and Hanan H Georgey, and Hussein I El-Subbagh
Imidazo[2,1-b]thiazole based indoleamine-2,3-dioxygenase 1 (IDO1) inhibitor: Structure based design, synthesis, bio-evaluation and docking studies.
November 2023, Bioorganic & medicinal chemistry letters,
Menna A Ewida, and Heba A Ewida, and Mahmoud S Ahmed, and Heba Abdelrasheed Allam, and Ramzia I ElBagary, and Riham F George, and Hanan H Georgey, and Hussein I El-Subbagh
[Dihydro-5,6-imidazo[2,1-b]thiazoles, dihydro-2,3-imidazo[2,1-b]benzothiazoles, analogs of levamisole].
May 1988, Il Farmaco; edizione scientifica,
Menna A Ewida, and Heba A Ewida, and Mahmoud S Ahmed, and Heba Abdelrasheed Allam, and Ramzia I ElBagary, and Riham F George, and Hanan H Georgey, and Hussein I El-Subbagh
Imidazo[2,1-b]thiazole derivatives as new inhibitors of 15-lipoxygenase.
November 2014, European journal of medicinal chemistry,
Menna A Ewida, and Heba A Ewida, and Mahmoud S Ahmed, and Heba Abdelrasheed Allam, and Ramzia I ElBagary, and Riham F George, and Hanan H Georgey, and Hussein I El-Subbagh
Design, synthesis and biological evaluation of imidazo[2,1-b]thiazole and benzo[d]imidazo[2,1-b]thiazole derivatives as Mycobacterium tuberculosis pantothenate synthetase inhibitors.
March 2016, Bioorganic & medicinal chemistry,
Menna A Ewida, and Heba A Ewida, and Mahmoud S Ahmed, and Heba Abdelrasheed Allam, and Ramzia I ElBagary, and Riham F George, and Hanan H Georgey, and Hussein I El-Subbagh
Diaryl hydroxylamines as pan or dual inhibitors of indoleamine 2,3-dioxygenase-1, indoleamine 2,3-dioxygenase-2 and tryptophan dioxygenase.
January 2019, European journal of medicinal chemistry,
Menna A Ewida, and Heba A Ewida, and Mahmoud S Ahmed, and Heba Abdelrasheed Allam, and Ramzia I ElBagary, and Riham F George, and Hanan H Georgey, and Hussein I El-Subbagh
Synthesis of New Thiazole Clubbed Imidazo[2,1-b]thiazole Hybrid as Antimycobacterial Agents.
January 2022, Medicinal chemistry (Shariqah (United Arab Emirates)),
Menna A Ewida, and Heba A Ewida, and Mahmoud S Ahmed, and Heba Abdelrasheed Allam, and Ramzia I ElBagary, and Riham F George, and Hanan H Georgey, and Hussein I El-Subbagh
Design, synthesis and biological evaluation of benzo-[d]-imidazo-[2,1-b]-thiazole and imidazo-[2,1-b]-thiazole carboxamide triazole derivatives as antimycobacterial agents.
August 2022, RSC advances,
Menna A Ewida, and Heba A Ewida, and Mahmoud S Ahmed, and Heba Abdelrasheed Allam, and Ramzia I ElBagary, and Riham F George, and Hanan H Georgey, and Hussein I El-Subbagh
Imidazo[2,1-b]thiazole-Coupled Natural Noscapine Derivatives as Anticancer Agents.
November 2019, ACS omega,
Menna A Ewida, and Heba A Ewida, and Mahmoud S Ahmed, and Heba Abdelrasheed Allam, and Ramzia I ElBagary, and Riham F George, and Hanan H Georgey, and Hussein I El-Subbagh
Research progress of indoleamine 2,3-dioxygenase inhibitors.
January 2015, Future medicinal chemistry,
Copied contents to your clipboard!