Ke, Chaoqi’s team published research in Organic Chemistry Frontiers in 2021 | CAS: 95-24-9

6-Chlorobenzothiazol-2-ylamine(cas: 95-24-9) belongs to thiazoles. Thiazoles are a class of five-membered rings containing nitrogen and sulfur with excellent antitumor, antiviral and antibiotic activities.Safety of 6-Chlorobenzothiazol-2-ylamineTheir presence in peptides or their ability to bind proteins, DNA and RNA has led to many synthetic studies and new applications.

The author of 《Organocatalytic asymmetric synthesis of benzothiazolopyrimidines via a [4+2] cycloaddition of azlactones with 2-benzothiazolimines》 were Ke, Chaoqi; Liu, Zhenzhong; Ruan, Sai; Feng, Xiaoming; Liu, Xiaohua. And the article was published in Organic Chemistry Frontiers in 2021. Safety of 6-Chlorobenzothiazol-2-ylamine The author mentioned the following in the article:

An easily available L-proline-derived guanidine-amide were found to be efficient at catalyzing a [4+2] cycloaddition of azlactones with 2-benzothiazolimines by affording various benzothiazolopyrimidines bearing adjacent tertiary and quaternary stereogenic centers in excellent yields at 2 mol% loading. The diastereoisomers of the main adducts differed from those in a previous bifunctional organocatalytic system. In the experiment, the researchers used 6-Chlorobenzothiazol-2-ylamine(cas: 95-24-9Safety of 6-Chlorobenzothiazol-2-ylamine)

6-Chlorobenzothiazol-2-ylamine(cas: 95-24-9) belongs to thiazoles. Thiazoles are a class of five-membered rings containing nitrogen and sulfur with excellent antitumor, antiviral and antibiotic activities.Safety of 6-Chlorobenzothiazol-2-ylamineTheir presence in peptides or their ability to bind proteins, DNA and RNA has led to many synthetic studies and new applications.

Referemce:
Thiazole | C3H3NS – PubChem,
Thiazole | chemical compound | Britannica

Prajapat, Prakash’s team published research in Heterocyclic Letters in 2021 | CAS: 95-24-9

6-Chlorobenzothiazol-2-ylamine(cas: 95-24-9) belongs to thiazoles. Thiazoles are a class of five-membered rings containing nitrogen and sulfur with excellent antitumor, antiviral and antibiotic activities.Name: 6-Chlorobenzothiazol-2-ylamineThe thiazole ring has been identified as a central feature of numerous natural products, perhaps the most famous example of which is epothilone.

In 2021,Heterocyclic Letters included an article by Prajapat, Prakash; Pappula, Venkata Narayana; Vaghani, Hasit; Agarwal, Shikha; Samota, Jayanti; Talesara, Ganpat L.. Name: 6-Chlorobenzothiazol-2-ylamine. The article was titled 《Synthesis of biologically potent alkoxyphthalimido plugged N-(2,4-dioxo-1,4-dihydroquinazolin)-3(2H)-yl)-4-oxo-4H-benzo[4,5]thiazolo[3,2-a]pyrimidine-3-carboxamide via Gould Jacobs reaction》. The information in the text is summarized as follows:

Convenient methods for the synthesis of new alkoxyphthalimidoquinazolinedione and their pyrimidobenzothiazole derivatives I [R1 = H, Cl, O2N; R2 = H, 2-(1,3-dioxoisoindolin-2-yl)oxyethyl] were reported. A series of benzothiazolopyrimidine-3-carboxamides I were prepared starting from substituted 2-aminobenzothiazoles via solvent free multi-component Gould-Jacobs reaction. Structures of newly synthesized compounds were established based on IR, 1H-NMR, mass, anal. studies and fluorescence tests. Some of synthesized mols. I were assayed for their antimalarial activity. IC50 values of antimalarial activity of compounds were also determined The results came from multiple reactions, including the reaction of 6-Chlorobenzothiazol-2-ylamine(cas: 95-24-9Name: 6-Chlorobenzothiazol-2-ylamine)

6-Chlorobenzothiazol-2-ylamine(cas: 95-24-9) belongs to thiazoles. Thiazoles are a class of five-membered rings containing nitrogen and sulfur with excellent antitumor, antiviral and antibiotic activities.Name: 6-Chlorobenzothiazol-2-ylamineThe thiazole ring has been identified as a central feature of numerous natural products, perhaps the most famous example of which is epothilone.

Referemce:
Thiazole | C3H3NS – PubChem,
Thiazole | chemical compound | Britannica

Yu, Jiaxue’s team published research in Pigment & Resin Technology in 2022 | CAS: 95-24-9

6-Chlorobenzothiazol-2-ylamine(cas: 95-24-9) belongs to thiazoles. Thiazoles are a class of five-membered rings containing nitrogen and sulfur with excellent antitumor, antiviral and antibiotic activities.Application In Synthesis of 6-Chlorobenzothiazol-2-ylamineTheir presence in peptides or their ability to bind proteins, DNA and RNA has led to many synthetic studies and new applications.

The author of 《Synthesis of benzothiazole-azo disperse dyes for high resistance to alkaline treatments and peroxide bleaching》 were Yu, Jiaxue; Tang, Jinglin; Wang, Xiaoyan; Du, Jinmei; Xu, Changhai; Zhang, Shansheng. And the article was published in Pigment & Resin Technology in 2022. Application In Synthesis of 6-Chlorobenzothiazol-2-ylamine The author mentioned the following in the article:

Purpose: This paper aims to synthesize benzothiazole-azo disperse dyes which can be applied not only for dyeing and alk. reduction of polyester fabric in one bath, but also for dyeing and peroxide bleaching of cotton/polyester blend fabric in one bath. Design/methodol./approach: The synthesized benzothiazole-azo disperse dyes were confirmed by proton NMR (1H-NMR) spectroscopy, mass spectroscopy (MS) and UV-visible spectrophotometry. The performance on resistance to alk. treatment and peroxide bleaching was tested by measuring the color strength of polyester fabric dyed with the synthesized benzothiazole-azo disperse dyes under high-temperature and high-pressure conditions. Findings: Increasing the electron-withdrawing ability of the substituents in the diazo component and the electron-donating ability of the substituents in the coupling component resulted in a significant bathochromic shift of the maximum absorption wavelength. Except that the disperse dyes synthesized from the coupling components containing the hydroxyethyl group were unstable in alk. solution, all others exhibited high resistance to alk. treatment and peroxide bleaching. Practical implications: The synthesized benzothiazole-azo disperse dyes provide the opportunities to combine dyeing and alk. reduction of polyester fabric into one bath, and combine dyeing and peroxide bleaching of cotton/polyester blend fabric into one bath. Originality/value: The synthesized benzothiazole-azo disperse dyes help to establish short processes of polyester and polyester/cotton blend fabrics so as to reduce energy consumption and raise production efficiency. The experimental part of the paper was very detailed, including the reaction process of 6-Chlorobenzothiazol-2-ylamine(cas: 95-24-9Application In Synthesis of 6-Chlorobenzothiazol-2-ylamine)

6-Chlorobenzothiazol-2-ylamine(cas: 95-24-9) belongs to thiazoles. Thiazoles are a class of five-membered rings containing nitrogen and sulfur with excellent antitumor, antiviral and antibiotic activities.Application In Synthesis of 6-Chlorobenzothiazol-2-ylamineTheir presence in peptides or their ability to bind proteins, DNA and RNA has led to many synthetic studies and new applications.

Referemce:
Thiazole | C3H3NS – PubChem,
Thiazole | chemical compound | Britannica

Zhu, Yu-Shen’s team published research in Chinese Chemical Letters in 2022 | CAS: 95-24-9

6-Chlorobenzothiazol-2-ylamine(cas: 95-24-9) belongs to thiazoles. Thiazoles are a class of five-membered rings containing nitrogen and sulfur with excellent antitumor, antiviral and antibiotic activities.Category: thiazoleThiazoles can also be used as protected formyl groups, which can be released in later stages of complex natural product synthesis.

Category: thiazoleOn March 31, 2022, Zhu, Yu-Shen; Shi, Linlin; Fu, Lianrong; Chen, Xiran; Zhu, Xinju; Hao, Xin-Qi; Song, Mao-Ping published an article in Chinese Chemical Letters. The article was 《Iodine-catalyzed amination of benzothiazoles with KSeCN in water to access primary 2-aminobenzothiazoles》. The article mentions the following:

A facile and sustainable approach for the amination of benzothiazoles I (X = H, N; R = H, 4-Cl, 5-OMe, 6-NO2, 7-C(O)OMe; R1 = H) with KSeCN using iodine as the catalyst in water has been disclosed under transition-metal free conditions. The reaction proceeded smoothly to afford various primary 2-amino benzothiazoles I (R1 = NH2) in up to 96% yield. A series of control experiments were performed, suggesting that a ring-opening mechanism was involved via a radical process. This protocol provides efficient synthesis of primary 2-aminobenzothiazole I (R1 = NH2). After reading the article, we found that the author used 6-Chlorobenzothiazol-2-ylamine(cas: 95-24-9Category: thiazole)

6-Chlorobenzothiazol-2-ylamine(cas: 95-24-9) belongs to thiazoles. Thiazoles are a class of five-membered rings containing nitrogen and sulfur with excellent antitumor, antiviral and antibiotic activities.Category: thiazoleThiazoles can also be used as protected formyl groups, which can be released in later stages of complex natural product synthesis.

Referemce:
Thiazole | C3H3NS – PubChem,
Thiazole | chemical compound | Britannica

He, Wei-Bao’s team published research in Chinese Chemical Letters in 2020 | CAS: 95-24-9

6-Chlorobenzothiazol-2-ylamine(cas: 95-24-9) belongs to thiazoles. Thiazoles are a class of five-membered rings containing nitrogen and sulfur with excellent antitumor, antiviral and antibiotic activities.Name: 6-Chlorobenzothiazol-2-ylamineThe thiazole ring has been identified as a central feature of numerous natural products, perhaps the most famous example of which is epothilone.

He, Wei-Bao; Gao, Lan-Qing; Chen, Xin-Jie; Wu, Zhi-Lin; Huang, Ying; Cao, Zhong; Xu, Xin-Hua; He, Wei-Min published an article in Chinese Chemical Letters. The title of the article was 《Visible-light-initiated malic acid-promoted cascade coupling/cyclization of aromatic amines and KSCN to 2-aminobenzothiazoles without photocatalyst》.Name: 6-Chlorobenzothiazol-2-ylamine The author mentioned the following in the article:

By using ambient air as the oxidant and malic acid as the promoter, a practical method for the preparation of 2-aminobenzothiazoles through visible-light-initiated cascade reaction of aromatic amines and KSCN in eco-friendly bis(methoxypropy)ether under metal-, hazardous additive-, photocatalyst-free conditions was established.6-Chlorobenzothiazol-2-ylamine(cas: 95-24-9Name: 6-Chlorobenzothiazol-2-ylamine) was used in this study.

6-Chlorobenzothiazol-2-ylamine(cas: 95-24-9) belongs to thiazoles. Thiazoles are a class of five-membered rings containing nitrogen and sulfur with excellent antitumor, antiviral and antibiotic activities.Name: 6-Chlorobenzothiazol-2-ylamineThe thiazole ring has been identified as a central feature of numerous natural products, perhaps the most famous example of which is epothilone.

Referemce:
Thiazole | C3H3NS – PubChem,
Thiazole | chemical compound | Britannica

P, Keerthana’s team published research in Journal of Fluorescence in 2022 | CAS: 95-24-9

6-Chlorobenzothiazol-2-ylamine(cas: 95-24-9) belongs to thiazoles. Thiazoles are a class of five-membered rings containing nitrogen and sulfur with excellent antitumor, antiviral and antibiotic activities.Formula: C7H5ClN2SThiazoles can also be used as protected formyl groups, which can be released in later stages of complex natural product synthesis.

Formula: C7H5ClN2SOn May 31, 2022, P, Keerthana; Abbo, Hanna; Cherian, Anila Rose; Titinchi, Salam; Varghese, Anitha published an article in Journal of Fluorescence. The article was 《An Efficient Inclusion Complex Based Fluorescent Sensor for Mercury (II) and its Application in Live-Cell Imaging》. The article mentions the following:

The formation of an inclusion complex between hydroxypropyl-β-cyclodextrin (H-CD) and 4-acetylphenyl-4-(((6-chlorobenzo[d]thiazol-2-yl)-imino)-methyl)-benzoate (L) was investigated by FT-IR, 1H-NMR, X-ray diffraction (XRD), FT-Raman, scanning electron microscope (SEM) techniques in the solid-state, absorption and emission spectroscopy in the liquid state and the virtual state as mol. docking technique. The binding properties of the inclusion complex (H-CD: L) with cations in deionized water was observed via absorbance and photoluminescence (PL) emission spectroscopy. The fluorescence probe (H-CD: L) inclusion complex (IC) was examined for several heavy metal cations, and identified that the PL emission wavelength of the complex displayed a continuous rise in the fluorescence intensity for Hg2+. A linearity range of 1 x 10-8 – 11 x 10-8 M and limit of detection value of 2.71 x 10-10 M was found to be achieved for the detection of Hg2+. This outcome proves that the inclusion complex H-CD: L would be a promising material for the development a solid-state fluorescence probe for detecting Hg2+. It also shows application in real sample anal. and cell imaging. In addition to this study using 6-Chlorobenzothiazol-2-ylamine, there are many other studies that have used 6-Chlorobenzothiazol-2-ylamine(cas: 95-24-9Formula: C7H5ClN2S) was used in this study.

6-Chlorobenzothiazol-2-ylamine(cas: 95-24-9) belongs to thiazoles. Thiazoles are a class of five-membered rings containing nitrogen and sulfur with excellent antitumor, antiviral and antibiotic activities.Formula: C7H5ClN2SThiazoles can also be used as protected formyl groups, which can be released in later stages of complex natural product synthesis.

Referemce:
Thiazole | C3H3NS – PubChem,
Thiazole | chemical compound | Britannica

Mor, Satbir’s team published research in Synthetic Communications in 2022 | CAS: 95-24-9

6-Chlorobenzothiazol-2-ylamine(cas: 95-24-9) belongs to thiazoles. Thiazoles are a class of five-membered rings containing nitrogen and sulfur with excellent antitumor, antiviral and antibiotic activities.Electric Literature of C7H5ClN2SThiazoles can also be used as protected formyl groups, which can be released in later stages of complex natural product synthesis.

《Regioselective synthesis of benzo[b]indeno[1,2-e][1,4]thiazin-11(10aH)-ones and antimicrobial evaluation thereof》 was published in Synthetic Communications in 2022. These research results belong to Mor, Satbir; Khatri, Mohini. Electric Literature of C7H5ClN2S The article mentions the following:

Benzo[b]indeno[1,2-e][1,4]thiazin-11(10aH)-ones I [R = 2-F, 3-F, 4-Cl; R1 = H, Cl, Br, Me, MeO] were synthesized regioselectively via cyclocondensation of 2,5-dibromo-2-(substitutedphenyl)-1H-indene-1,3(2H)-diones and 2-aminobenzenethiols using freshly dried EtOH as solvent with 42-60% yields. The synthesized derivatives I were well-characterized by employing different spectral techniques (FTIR, 1H and 13C NMR, and HRMS) and X-ray crystallog. anal. All the derivatives I were examined for their preliminary in vitro antimicrobial activity against two Gram-pos. bacterial strains, i.e., B. subtilis, and S. aureus, two Gram-neg. bacterial strains, i.e., P. aeruginosa and E. coli, and two fungal strains, i.e., C. albicans and R. oryzae employing serial dilution method taking Ciprofloxacin and Fluconazole as standard reference drugs for antibacterial and antifungal activities, resp. Among all the tested derivatives I, derivative I [R = 4-Cl; R1 = Br] was found to exhibit significant inhibition against all the microbial strains under study. In the experimental materials used by the author, we found 6-Chlorobenzothiazol-2-ylamine(cas: 95-24-9Electric Literature of C7H5ClN2S)

6-Chlorobenzothiazol-2-ylamine(cas: 95-24-9) belongs to thiazoles. Thiazoles are a class of five-membered rings containing nitrogen and sulfur with excellent antitumor, antiviral and antibiotic activities.Electric Literature of C7H5ClN2SThiazoles can also be used as protected formyl groups, which can be released in later stages of complex natural product synthesis.

Referemce:
Thiazole | C3H3NS – PubChem,
Thiazole | chemical compound | Britannica

Liu, Hongtao’s team published research in RSC Medicinal Chemistry in 2020 | CAS: 95-24-9

6-Chlorobenzothiazol-2-ylamine(cas: 95-24-9) belongs to thiazoles. Thiazoles are a class of five-membered rings containing nitrogen and sulfur with excellent antitumor, antiviral and antibiotic activities.Reference of 6-Chlorobenzothiazol-2-ylamineThiazoles can also be used as protected formyl groups, which can be released in later stages of complex natural product synthesis.

《Identification of N-benzothiazolyl-2-benzenesulfonamides as novel ABCA1 expression upregulators》 was published in RSC Medicinal Chemistry in 2020. These research results belong to Liu, Hongtao; Jiang, Xinhai; Gao, Xinfeng; Tian, Wenhua; Xu, Chen; Wang, Ruizhi; Xu, Yanni; Wei, Liping; Cao, Feng; Li, Wenyan. Reference of 6-Chlorobenzothiazol-2-ylamine The article mentions the following:

ATP binding cassette transporter A1 (ABCA1) is a critical transporter that mediates cellular cholesterol efflux from macrophages to apolipoprotein A-I (ApoA-I). Therefore, increasing the expression level of ABCA1 is anti-atherogenic and ABCA1 expression upregulators have become novel choices for atherosclerosis treatment. In this study, a series of N-benzothiazolyl-2-benzenesulfonamides, based on the structure of WY06 discovered in our laboratory, were designed and synthesized as novel ABCA1 expression upregulators. Based on an in vitro ABCA1 upregulatory cell model, ABCA1 upregulation of target compounds was evaluated. Compounds 6c, 6d, and 6i have good upregulated ABCA1 expression activities, with EC50 values of 0.97, 0.37, and 0.41μM, resp. A preliminary structure-activity relationship is summarized. Replacing the methoxy group on the benzothiazole moiety of WY06 with a fluorine or chlorine atom and exchanging the ester group with a cyano group resulted in more potent ABCA1 upregulating activity. Moreover, compound 6i increased ABCA1 mRNA and protein expression and significantly promoted cholesterol efflux in RAW264.7 cells. In conclusion, N-benzothiazolyl-2-benzenesulfonamides were identified as novel ABCA1 expression upregulators. In the experimental materials used by the author, we found 6-Chlorobenzothiazol-2-ylamine(cas: 95-24-9Reference of 6-Chlorobenzothiazol-2-ylamine)

6-Chlorobenzothiazol-2-ylamine(cas: 95-24-9) belongs to thiazoles. Thiazoles are a class of five-membered rings containing nitrogen and sulfur with excellent antitumor, antiviral and antibiotic activities.Reference of 6-Chlorobenzothiazol-2-ylamineThiazoles can also be used as protected formyl groups, which can be released in later stages of complex natural product synthesis.

Referemce:
Thiazole | C3H3NS – PubChem,
Thiazole | chemical compound | Britannica

Zhang, Yan’s team published research in Chinese Chemical Letters in 2022 | CAS: 95-24-9

6-Chlorobenzothiazol-2-ylamine(cas: 95-24-9) belongs to thiazoles. Thiazoles are a class of five-membered rings containing nitrogen and sulfur with excellent antitumor, antiviral and antibiotic activities.Quality Control of 6-Chlorobenzothiazol-2-ylamineTheir presence in peptides or their ability to bind proteins, DNA and RNA has led to many synthetic studies and new applications.

Zhang, Yan; Li, Yuxin; Li, Huan; Shang, Junfeng; Li, Zhengming; Wang, Baolei published an article on January 31 ,2022. The article was titled 《Synthesis and insecticidal evaluation of novel sulfide-containing amide derivatives as potential ryanodine receptor modulators》, and you may find the article in Chinese Chemical Letters.Quality Control of 6-Chlorobenzothiazol-2-ylamine The information in the text is summarized as follows:

With the aim of discovering new bioactive pesticides for crop protection, a series of novel sulfide-containing amide derivatives A were efficiently synthesized via a strategy of modifying the “”amide”” structure of anthranilic diamide insecticides. The single-crystal structures of A2-3 and A4-5 were firstly reported. The bioassay results showed that most of the synthesized compounds display moderate to high insecticidal activities. Particularly, some sulfone-containing compounds, e.g.,A2-3,A3-3 and A6-3, not only possessed favorable lethality rate (50%-100%) against P. xylostella at a concentration of 0.1 mg/L, but also held good activities towards a variety of agricultural pests such as M. separata, C. pipiens pallen, H. armigera and O. nubilalis; the larvicidal activities of A4-1 and A6-1 towards P. xylostella were close to that of chlorantraniliprole at 0.01 mg/L. The calcium imaging experiments revealed that the representative compounds A2-3 and A6-3 are potential ryanodine receptor (RyR) modulators. The structure-activity relationships were discussed in detail. These results provide useful information for further design and development of novel insecticides. In the experiment, the researchers used many compounds, for example, 6-Chlorobenzothiazol-2-ylamine(cas: 95-24-9Quality Control of 6-Chlorobenzothiazol-2-ylamine)

6-Chlorobenzothiazol-2-ylamine(cas: 95-24-9) belongs to thiazoles. Thiazoles are a class of five-membered rings containing nitrogen and sulfur with excellent antitumor, antiviral and antibiotic activities.Quality Control of 6-Chlorobenzothiazol-2-ylamineTheir presence in peptides or their ability to bind proteins, DNA and RNA has led to many synthetic studies and new applications.

Referemce:
Thiazole | C3H3NS – PubChem,
Thiazole | chemical compound | Britannica

Tokala, Ramya’s team published research in Bioorganic Chemistry in 2021 | CAS: 95-24-9

6-Chlorobenzothiazol-2-ylamine(cas: 95-24-9) belongs to thiazoles. Thiazoles are a class of five-membered rings containing nitrogen and sulfur with excellent antitumor, antiviral and antibiotic activities.Computed Properties of C7H5ClN2STheir presence in peptides or their ability to bind proteins, DNA and RNA has led to many synthetic studies and new applications.

Tokala, Ramya; Mahajan, Surbhi; Kiranmai, Gaddam; Sigalapalli, Dilep Kumar; Sana, Sravani; John, Stephy Elza; Nagesh, Narayana; Shankaraiah, Nagula published an article on January 31 ,2021. The article was titled 《Development of β-carboline-benzothiazole hybrids via carboxamide formation as cytotoxic agents: DNA intercalative topoisomerase IIα inhibition and apoptosis induction》, and you may find the article in Bioorganic Chemistry.Computed Properties of C7H5ClN2S The information in the text is summarized as follows:

In quest of promising anticancer agents, the pharmacophores of natural (β-carboline) and synthetic origin (benzothiazole) were adjoined by a carboxamide bridge and three-point diversification was accomplished. The in vitro cytotoxic ability of the compounds was established on adherent and suspension human cancer cell lines and compounds I and II advanced as pre-eminent mols. with IC50 values of 1.46 and 1.81μM resp. in A549 cell line. The cytospecificity was entrenched for potent compounds I and II by evaluating against normal human lung epithelial cells and selectivity index was calculated Furthermore, EtBr displacement, relative viscosity and gel-based topoisomerase II target assays unveiled the intercalative topo-II inhibitory capability and DNA binding studies (absorbance) revealed the dissociation constant (Kd) for compounds I and II as 98 and 103μM resp. Addnl., cell-based flow cytometric assays like Annexin-V/PI dual staining aids in the quantification of apoptosis induced and JC-1 staining disclosed the depolarization of mitochondrial membrane potential by compound I in A549 cells in a dose-dependent manner. Moreover, wound healing assay established the inhibition of in vitro cell migration by compound I on A549 cells. In addition, mol. docking studies proved the binding of compounds I and II in the active site of DNA complexed with topo IIα and stabilized by interactions with DNA base pairs and amino acid residues. Remarkably, the compounds I and II follow Lipinski’s rule of five and are in the recommended range for Jorgensen’s rule of three with a minimal violation and other pharmacokinetic parameters revealing druggability of the synthesized hybrids. In the experiment, the researchers used 6-Chlorobenzothiazol-2-ylamine(cas: 95-24-9Computed Properties of C7H5ClN2S)

6-Chlorobenzothiazol-2-ylamine(cas: 95-24-9) belongs to thiazoles. Thiazoles are a class of five-membered rings containing nitrogen and sulfur with excellent antitumor, antiviral and antibiotic activities.Computed Properties of C7H5ClN2STheir presence in peptides or their ability to bind proteins, DNA and RNA has led to many synthetic studies and new applications.

Referemce:
Thiazole | C3H3NS – PubChem,
Thiazole | chemical compound | Britannica