Category: thiazole

In 2020,Pharmacognosy Journal included an article by Tsilo, Phakamani Hopewell; Maliehe, Sidney Tsolanku; Shandu, Jabulani Siyabonga; Khan, Rene. Recommanded Product: 30931-67-0. The article was titled 《Chemical composition and some biological activities of the methanolic Encephalartos ferox fruit extract》. The information in the text is summarized as follows:

Although literature reports the therapeutic properties of Encephalartos ferox, there are limited pharmacol. studies of its fruit. This study sought to evaluate the antibacterial, antioxidant, anti-quorum sensing, and in vitro cytotoxic activities of the methanolic E. ferox fruit extract The chem. constituent of the methanolic fruit extract was analyzed using gas chromatog.-mass spectrometry. Antibacterial activity of the extract was investigated against Staphylococcus aureus (ATCC 25923), Bacillus cereus (ATCC 10102), Escherichia coli (ATCC 25922) and Pseudomonas aeruginosa (ATCC 27853) using the broth dilution method. The standard 2.2-diphenyl-1-picrylhydrazyl (DPPH) and 2.2-azinobis (3-ethylbenzothiazoline-6-sulfonic acid) (ABTS) methods were used to evaluate the scavenging activities of the extract Anti-quorum sensing activity was assessed against biosensor strain-Chromobacterium violaceum (ATCC 12472). Cytotoxicity in HepG2 cells was investigated using the tetrazolium-based colorimetric (MTT) assay. The extract revealed eight volatile compounds with cis-Vaccenic acid (87.06%) and 9-Octadecenoic acid, 1,2,3-propanetriyl ester (5.21%) as the major components. Antibacterial activity against all tested strains with min. inhibitory concentration range of 1.56 – 12.5 mg/mL was observed The DPPH and ABTS assays demonstrated scavenging activities with the median inhibitory concentration (IC50) values of 0.09 mg/mL and 0.003 mg/mL, resp. The extract also displayed strong anti-quorum sensing activity with 93% inhibition of violacein production at 25 mg/mL. A half maximum inhibitory concentration (IC50) of 5370 μg/mL was computed in HepG2 cells. The extract has potential to be used as a source of therapeutic compounds in pharmaceutical applications. In the experimental materials used by the author, we found ABTS Diammonium(cas: 30931-67-0Recommanded Product: 30931-67-0)

ABTS Diammonium(cas: 30931-67-0) belongs to anime. Amines can be classified according to the nature and number of substituents on nitrogen. Aliphatic amines contain only H and alkyl substituents. Aromatic amines have the nitrogen atom connected to an aromatic ring.Important amines include amino acids, biogenic amines, trimethylamine, and aniline. Inorganic derivatives of ammonia are also called amines, such as monochloramine (NClH2).Recommanded Product: 30931-67-0

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

Product Details of 95-24-9On May 31, 2019, Yamano, Tomoyoshi; Dobes, Jan; Voboril, Matous; Steinert, Madlen; Brabec, Tomas; Zietara, Natalia; Dobesova, Martina; Ohnmacht, Caspar; Laan, Martti; Peterson, Part; Benes, Vladimir; Sedlacek, Radislav; Hanayama, Rikinari; Kolar, Michal; Klein, Ludger; Filipp, Dominik published an article in Journal of Experimental Medicine. The article was 《Aire-expressing ILC3-like cells in the lymph node display potent APC features》. The article mentions the following:

The autoimmune regulator (Aire) serves an essential function for T cell tolerance by promoting the “”promiscuous”” expression of tissue antigens in thymic epithelial cells. Aire is also detected in rare cells in peripheral lymphoid organs, but the identity of these cells is poorly understood. Here, we report that Aire protein-expressing cells in lymph nodes exhibit typical group 3 innate lymphoid cell (ILC3) characteristics such as lymphoid morphol., absence of “”classical”” hematopoietic lineage markers, and dependence on RORγt. Aire+ cells are more frequent among lineage-neg. RORγt+ cells of peripheral lymph nodes as compared with mucosa-draining lymph nodes, display a unique Aire-dependent transcriptional signature, express high surface levels of MHCII and costimulatory mols., and efficiently present an endogenously expressed model antigen to CD4+ T cells. These findings define a novel type of ILC3-like cells with potent APC features, suggesting that these cells serve a function in the control of T cell responses. The experimental process involved the reaction of 6-Chlorobenzothiazol-2-ylamine(cas: 95-24-9Product Details of 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.Product Details of 95-24-9The 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

In 2022,Taft, Benjamin R.; Yokokawa, Fumiaki; Kirrane, Tom; Mata, Anne-Catherine; Huang, Richard; Blaquiere, Nicole; Waldron, Grace; Zou, Bin; Simon, Oliver; Vankadara, Subramanyam; Chan, Wai Ling; Ding, Mei; Sim, Sandra; Straimer, Judith; Guiguemde, Armand; Lakshminarayana, Suresh B.; Jain, Jay Prakash; Bodenreider, Christophe; Thompson, Christopher; Lanshoeft, Christian; Shu, Wei; Fang, Eric; Qumber, Jafri; Chan, Katherine; Pei, Luying; Chen, Yen-Liang; Schulz, Hanna; Lim, Jessie; Abas, Siti Nurdiana; Ang, Xiaoman; Liu, Yugang; Angulo-Barturen, Inigo; Jimenez-Diaz, Maria Belen; Gamo, Francisco Javier; Crespo-Fernandez, Benigno; Rosenthal, Philip J.; Cooper, Roland A.; Tumwebaze, Patrick; Aguiar, Anna Caroline Campos; Campo, Brice; Campbell, Simon; Wagner, Jurgen; Diagana, Thierry T.; Sarko, Christopher published an article in Journal of Medicinal Chemistry. The title of the article was 《Discovery and Preclinical Pharmacology of INE963, a Potent and Fast-Acting Blood-Stage Antimalarial with a High Barrier to Resistance and Potential for Single-Dose Cures in Uncomplicated Malaria》.Application of 3034-22-8 The author mentioned the following in the article:

A series of 5-aryl-2-amino-imidazothiadiazole (ITD) derivatives were identified by a phenotype-based high-throughput screening using a blood stage Plasmodium falciparum (Pf) growth inhibition assay. A lead optimization program focused on improving antiplasmodium potency, selectivity against human kinases, and absorption, distribution, metabolism, excretion, and toxicity properties and extended pharmacol. profiles culminated in the identification of INE963 (1)(I), which demonstrates potent cellular activity against Pf 3D7 (EC50 = 0.006 μM) and achieves “”artemisinin-like”” kill kinetics in vitro with a parasite clearance time of <24 h. A single dose of 30 mg/kg is fully curative in the Pf-humanized severe combined immunodeficient mouse model. INE963 (1) also exhibits a high barrier to resistance in drug selection studies and a long half-life (T1/2) across species. These properties suggest the significant potential for INE963 (1) to provide a curative therapy for uncomplicated malaria with short dosing regimens. For these reasons, INE963 (1) was progressed through GLP toxicol. studies and is now undergoing Ph1 clin. trials. In the experiment, the researchers used 5-Bromothiazol-2-amine(cas: 3034-22-8Application of 3034-22-8)

5-Bromothiazol-2-amine(cas: 3034-22-8) belongs to anime. Reduction of nitro compounds, RNO2, by hydrogen or other reducing agents produces primary amines cleanly (i.e., without a mixture of products), but the method is mostly used for aromatic amines because of the limited availability of aliphatic nitro compounds. Reduction of nitriles and oximes (R2C=NOH) also yields primary amines.Application of 3034-22-8

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

In 2012,Sarabu, Ramakanth; Bizzarro, Fred T.; Corbett, Wendy L.; Dvorozniak, Mark T.; Geng, Wanping; Grippo, Joseph F.; Haynes, Nancy-Ellen; Hutchings, Stanley; Garofalo, Lisa; Guertin, Kevin R.; Hilliard, Darryl W.; Kabat, Marek; Kester, Robert F.; Ka, Wang; Liang, Zhenmin; Mahaney, Paige E.; Marcus, Linda; Matschinsky, Franz M.; Moore, David; Racha, Jagdish; Radinov, Roumen; Ren, Yi; Qi, Lida; Pignatello, Michael; Spence, Cheryl L.; Steele, Thomas; Tengi, John; Grimsby, Joseph published 《Discovery of Piragliatin-First Glucokinase Activator Studied in Type 2 Diabetic Patients》.Journal of Medicinal Chemistry published the findings.Name: 5-Bromothiazol-2-amine The information in the text is summarized as follows:

Glucokinase (GK) activation as a potential strategy to treat type 2 diabetes (T2D) is well recognized. Compound 1, a glucokinase activator (GKA) lead that we have previously disclosed, caused reversible hepatic lipidosis in repeat-dose toxicol. studies. We hypothesized that the hepatic lipidosis was due to the structure-based toxicity and later established that it was due to the formation of a thiourea metabolite, 2. Subsequent SAR studies of 1 led to the identification of a pyrazine-based lead analog 3, lacking the thiazole moiety. In vivo metabolite identification studies, followed by the independent synthesis and profiling of the cyclopentyl keto- and hydroxyl- metabolites of 3, led to the selection of piragliatin, 4, as the clin. lead. Piragliatin was found to lower pre- and postprandial glucose levels, improve the insulin secretory profile, increase β-cell sensitivity to glucose, and decrease hepatic glucose output in patients with T2D. After reading the article, we found that the author used 5-Bromothiazol-2-amine(cas: 3034-22-8Name: 5-Bromothiazol-2-amine)

5-Bromothiazol-2-amine(cas: 3034-22-8) belongs to anime. Reaction with nitrous acid (HNO2), which functions as an acylating agent that is a source of the nitrosyl group (―NO), converts aliphatic primary amines to nitrogen and mixtures of alkenes and alcohols corresponding to the alkyl group in a complex process. This reaction has been used for analytical determination of primary amino groups in a procedure known as the Van Slyke method.Name: 5-Bromothiazol-2-amine

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

In 2011,Edwards, Geoffrey; Helm, Alison; Hellier, Jennifer; Korba, Brent E.; Semple, J. Edward; Rossignol, Jean-Francois published 《Thiazolides as Novel Antiviral Agents. 2. Inhibition of Hepatitis C Virus Replication》.Journal of Medicinal Chemistry published the findings.Formula: C3H3BrN2S The information in the text is summarized as follows:

We report the activities of a number of thiazolides [2-hydroxyaroyl-N-(thiazol-2-yl)amides] against hepatitis C virus (HCV) genotypes IA and IB, using replicon assays. The structure-activity relationships (SARs) of thiazolides against HCV are less predictable than against hepatitis B virus (HBV), though an electron-withdrawing group at C(5′) generally correlates with potency. Among the related salicyloylanilides, the m-fluorophenyl analog was most promising; niclosamide and close analogs suffered from very low solubility and bioavailability. Nitazoxanide (NTZ) 1 has performed well in clin. trials against HCV. We show here that the 5′-Cl analog 4 (I) has closely comparable in vitro activity and a good cell safety index. By use of support vector anal., a quant. structure-activity relationship (QSAR) model was obtained, showing good predictive models for cell safety. We conclude by updating the mode of action of the thiazolides and explain the candidate selection that has led to compound 4 entering preclin. development. In the experimental materials used by the author, we found 5-Bromothiazol-2-amine(cas: 3034-22-8Formula: C3H3BrN2S)

5-Bromothiazol-2-amine(cas: 3034-22-8) belongs to anime. Amine, any member of a family of nitrogen-containing organic compounds that is derived, either in principle or in practice, from ammonia (NH3). Naturally occurring amines include the alkaloids, which are present in certain plants; the catecholamine neurotransmitters (i.e., dopamine, epinephrine, and norepinephrine); and a local chemical mediator, histamine, that occurs in most animal tissues.Formula: C3H3BrN2S

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

In 2006,Jung, Frederic H.; Pasquet, Georges; Van der Brempt, Christine Lambert; Lohmann, Jean-Jacques M.; Warin, Nicolas; Renaud, Fabrice; Germain, Herve; De Savi, Chris; Roberts, Nicola; Johnson, Trevor; Dousson, Cyril; Hill, George B.; Mortlock, Andrew A.; Heron, Nicola; Wilkinson, Robert W.; Wedge, Stephen R.; Heaton, Simon P.; Odedra, Rajesh; Keen, Nicholas J.; Green, Stephen; Brown, Elaine; Thompson, Katherine; Brightwell, Stephen published 《Discovery of Novel and Potent Thiazoloquinazolines as Selective Aurora A and B Kinase Inhibitors》.Journal of Medicinal Chemistry published the findings.Application of 3034-22-8 The information in the text is summarized as follows:

The synthesis of a novel series of quinazolines substituted at C4 by five-membered ring aminoheterocycles is reported. Their in vitro structure-activity relationships vs. Aurora A and B serine-threonine kinases is discussed. Our results demonstrate that quinazolines with a substituted aminothiazole at C4 possess potent Aurora A and B inhibitory activity and excellent selectivity against a panel of various serine-threonine and tyrosine kinases, as exemplified by N-(3-fluorophenyl)-2-[2-[[7-[3-[4-(hydroxymethyl)piperidin-1-yl]propoxy]-6-methoxy-quinazolinyl]amino]-1,3-thiazol-5-yl]acetamide (I). It was found also that the position and nature of the substituent on the thiazole play key roles in cellular potency. Compounds with an acetanilide substituent at C5′ have the greatest cellular activity. The importance of the C5′ position for substitution has been rationalized by ab initio MO calculations Results show that the planar conformation with the sulfur of the thiazole next to the quinazoline N-3 is strongly favored over the other possible planar conformation. I is a potent suppressor of the expression of phospho-histone H3 in tumor cells in vitro as well as in vivo, where I, administered as its phosphate prodrug suppresses the expression of phospho-histone H3 in s.c. implanted tumors in nude mice. The experimental process involved the reaction of 5-Bromothiazol-2-amine(cas: 3034-22-8Application of 3034-22-8)

5-Bromothiazol-2-amine(cas: 3034-22-8) belongs to anime. Reaction with nitrous acid (HNO2), which functions as an acylating agent that is a source of the nitrosyl group (―NO), converts aliphatic primary amines to nitrogen and mixtures of alkenes and alcohols corresponding to the alkyl group in a complex process. This reaction has been used for analytical determination of primary amino groups in a procedure known as the Van Slyke method.Application of 3034-22-8

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

Wang, Hefei; Zhao, He-Ping; Zhu, Lizhong published an article in Environmental Science & Technology. The title of the article was 《Role of Pyrogenic Carbon in Parallel Microbial Reduction of Nitrobenzene in the Liquid and Sorbed Phases》.Name: ABTS Diammonium The author mentioned the following in the article:

Surface functional groups and graphitic C comprise the electroactive components of pyrogenic C. The role of pyrogenic C with different electroactive components content in mediating electron transfer in biochem. reactions has not been systematically studied. The authors determined the pyrogenic C electron exchange capacity was 0.067-0.120 mmol e-/g pyrogenic C with maximum elec. conductivity (EC) of 4.85 S/cm. Nitrobenzene was simultaneously reduced in liquid and sorbed phases by Shewanella oneidensis strain MR-1 in the presence of pyrogenic C. Pyrogenic C did not affect aqueous nitrobenzene reduction; reduction of sorbed nitrobenzene was much slower than that of the aqueous species. Enhancing the pyrogenic C oxygenated functional moiety content by HNO3 oxidation elevated bio-reduction rates of aqueous and sorbed species. Anthraquinone groups were deemed the most likely oxygenated functional redox compounds based on voltammetric curve tests and spectroscopic anal. Pyrogenic C reactivity for mediating sorbed nitrobenzene reduction was pos. correlated with its EC, which was demonstrated to be related to condensed aromatic structures. This work elucidated the mechanism for pyrogenic C-mediated biotransformation of nitrobenzene and helped properly evaluate the pyrogenic C role in biogeochem. redox processes occurring in nature. In the experiment, the researchers used ABTS Diammonium(cas: 30931-67-0Name: ABTS Diammonium)

ABTS Diammonium(cas: 30931-67-0) belongs to anime. Primary amines having a tertiary alkyl group (R3CNH2) are difficult to prepare with most methods but are made industrially by the Ritter reaction. In this method a tertiary alcohol reacts with hydrogen cyanide (HCN) in the presence of a concentrated strong acid; a formamide, RNH―CHO, is formed first, which then undergoes hydrolysis.Name: ABTS Diammonium

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

Shad, Naveed Akhtar; Sajid, Muhammad Munir; Javed, Yasir; Ikram, Muhammad; Hussain, Muhammad Irfan; Nawaz, Somia; Afzal, Amir Muhammad; Hussain, Syed Zajif; Amin, Nasir; Yousuf, Imran published an article on January 31 ,2020. The article was titled 《Lamellar shape lead tungstate (PbWO4) nanostructures as synergistic catalyst for peroxidase mimetic activity》, and you may find the article in Materials Research Express.Recommanded Product: ABTS Diammonium The information in the text is summarized as follows:

Tungstate based nanomaterials have emerged as important class in transition metal oxide. In this study, Lead tungstate (PbWO4) nanostructures with lamellar morphol. were prepared by hydrothermal method. The synthesized materials were characterized by XRD, SEM, FTIR, DLS, BET and PL. Nitrogen adsorption-desorption measurements indicated that the surface area of the synthesized lamellar morphol. was ∼86.225 m2 g-1. The lamellar-like morphol. showed enhanced peroxidase-like activity owing to the large surface area, higher substrate interaction and efficient electron transportation. The results indicated higher reaction velocity (Vmax = 13.56 × 10-8 M s-1) and low Michaelis-Menten constant (km = 0.325 mM) value for nanostructures, providing evidence for higher affinity of novel structures towards the substrate and increased peroxidase-like activity. Finally, biocompatibility test was conducted by performing cytotoxicity experiments of PbWO4 nanostructures on MTT assays. The results came from multiple reactions, including the reaction of ABTS Diammonium(cas: 30931-67-0Recommanded Product: ABTS Diammonium)

ABTS Diammonium(cas: 30931-67-0) belongs to anime. The methylamines occur in small amounts in some plants. Many polyfunctional amines (i.e., those having other functional groups in the molecule) occur as alkaloids in plants—for example, mescaline, 2-(3,4,5-trimethoxyphenyl)ethylamine; the cyclic amines nicotine, atropine, morphine, and cocaine; and the quaternary salt choline, N-(2-hydroxyethyl)trimethylammonium chloride, which is present in nerve synapses and in plant and animal cells.Recommanded Product: ABTS Diammonium

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

Luci, Diane K.; Jameson, J. Brian II; Yasgar, Adam; Diaz, Giovanni; Joshi, Netra; Kantz, Auric; Markham, Kate; Perry, Steve; Kuhn, Norine; Yeung, Jennifer; Kerns, Edward H.; Schultz, Lena; Holinstat, Michael; Nadler, Jerry L.; Taylor-Fishwick, David A.; Jadhav, Ajit; Simeonov, Anton; Holman, Theodore R.; Maloney, David J. published an article on January 23 ,2014. The article was titled 《Synthesis and Structure-Activity Relationship Studies of 4-((2-Hydroxy-3-methoxybenzyl)amino)benzenesulfonamide Derivatives as Potent and Selective Inhibitors of 12-Lipoxygenase》, and you may find the article in Journal of Medicinal Chemistry.Synthetic Route of C7H3BrFNS The information in the text is summarized as follows:

Human lipoxygenases (LOXs) are a family of iron-containing enzymes which catalyze the oxidation of polyunsaturated fatty acids to provide the corresponding bioactive hydroxyeicosatetraenoic acid (HETE) metabolites. These eicosanoid signaling mols. are involved in a number of physiol. responses such as platelet aggregation, inflammation, and cell proliferation. Our group has taken a particular interest in platelet-type 12-(S)-LOX (12-LOX) because of its demonstrated role in skin diseases, diabetes, platelet hemostasis, thrombosis, and cancer. Herein, we report the identification and medicinal chem. optimization of a 4-((2-hydroxy-3-methoxybenzyl)-amino)-benzenesulfonamide-based scaffold. Top compounds, exemplified by I [R = 2-benzothiazole, 2-benzoxazole], display nM potency against 12-LOX, excellent selectivity over related lipoxygenases and cyclooxygenases, and possess favorable ADME properties. In addition, compounds I [R = 2-benzothiazole, 2-benzoxazole] inhibit PAR-4 induced aggregation and calcium mobilization in human platelets and reduce 12-HETE in β-cells.2-Bromo-6-fluorobenzothiazole(cas: 152937-04-7Synthetic Route of C7H3BrFNS) was used in this study.

2-Bromo-6-fluorobenzothiazole(cas: 152937-04-7) belongs to thiazoles. Thiazoles are a class of five-membered rings containing nitrogen and sulfur with excellent antitumor, antiviral and antibiotic activities.Synthetic Route of C7H3BrFNSTheir 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

Jiang, Chen Hao; Yuan, Xin; Li, Jiang Fen; Xie, Yu Fang; Zhang, An Zhi; Wang, Xue Li; Yang, Lan; Liu, Chun Xia; Liang, Wei Hua; Pang, Li Juan; Zou, Hong; Cui, Xiao Bin; Shen, Xi Hua; Qi, Yan; Jiang, Jin Fang; Gu, Wen Yi; Li, Feng; Hu, Jian Ming published their research in Journal of Translational Medicine on December 31 ,2020. The article was titled 《Bioinformatics-based screening of key genes for transformation of liver cirrhosis to hepatocellular carcinoma》.Recommanded Product: 6-Chlorobenzothiazol-2-ylamine The article contains the following contents:

Abstract: Background: The aims of the present study were to identify key genes related to the transformation of cirrhosis into HCC, and explore the associated mol. mechanisms. Methods: GSE89377, GSE17548, GSE63898 and GSE54236 mRNA microarray datasets from Gene Expression Omnibus (GEO) were analyzed to obtain differentially expressed genes (DEGs) between HCC and liver cirrhosis tissues, and network anal. of protein-protein interactions (PPIs) was carried out. String and Cytoscape were used to analyze modules and identify hub genes, Kaplan-Meier Plotter and Oncomine databases were used to explore relationships between hub genes and disease occurrence, development and prognosis of HCC, and the mol. mechanism of the main hub gene was probed using Kyoto Encyclopedia of Genes and Genomes(KEGG) pathway anal. Results: In total, 58 DEGs were obtained, of which 12 and 46 were up- and down-regulated, resp. Three hub genes (CDKN3, CYP2C9 and LCAT) were identified and associated prognostic information was obtained. CDKN3 may be correlated with the occurrence, invasion, and recurrence of HCC. Genes closely related to changes in the CDKN3 hub gene were screened, and Kyoto Encyclopedia of Genes and Genomes (KEGGs) pathway anal. identified numerous cell cycle-related genes. Conclusion: CDKN3 may affect the transformation of liver cirrhosis into HCC, and represents a new candidate mol. marker of the occurrence and progression of HCC. The experimental part of the paper was very detailed, including the reaction process of 6-Chlorobenzothiazol-2-ylamine(cas: 95-24-9Recommanded Product: 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.Recommanded Product: 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