(Bio)isosteres of ortho- and meta-substituted benzenes

• H. Erik Diepers and
• Johannes C. L. Walker

Beilstein J. Org. Chem. 2024, 20, 859–890, doi:10.3762/bjoc.20.78

• metallophotoredox coupling reactions to deliver nitrogen- and aryl-functionalised BCPs such as (±)-17 and (±)-18. In the reports of Baran, Collins and co-workers and of MacMillan and co-workers, isosteres of compounds including telmisartan (isostere = BCP 21) and lomitapide (isostere = BCP 22) were prepared and

• their physicochemical properties were compared to those of the parent compounds (Figure 3) [26][33]. The reported distribution coefficients (logD) of enantiomeric 1,2-BCPs (+)-21 and (−)-21 are very similar to telmisartan, while the distribution coefficients of the lomitapide isosteres (+)-22 and (−)-22

• are significantly increased compared with the parent compound. The observed aqueous solubilities of BCPs (+)-21 and (−)-21 were much higher than that of telmisartan. For the lomitapide isosteres (+)-22 and (−)-22, the solubility was different for each enantiomer; while 1,2-BCP (+)-22 showed increased

DDQ in mechanochemical C–N coupling reactions

• Shyamal Kanti Bera,
• Rosalin Bhanja and
• Prasenjit Mal

Beilstein J. Org. Chem. 2022, 18, 639–646, doi:10.3762/bjoc.18.64

• heterocyclic scaffolds holding a broad range of biological activities [41][42][43]. For example, telmisartan, a 1,2-disubstituted benzimidazole derivative, is extensively used as an antihypertensive agent [44]. The substrate scope for the synthesis of variously substituted benzimidazoles is shown in Figure 2

On the application of 3d metals for C–H activation toward bioactive compounds: The key step for the synthesis of silver bullets

• Renato L. Carvalho,
• Amanda S. de Miranda,
• Mateus P. Nunes,
• Roberto S. Gomes,
• Guilherme A. M. Jardim and
• Eufrânio N. da Silva Júnior

Beilstein J. Org. Chem. 2021, 17, 1849–1938, doi:10.3762/bjoc.17.126

Synthesis of purines and adenines containing the hexafluoroisopropyl group

• Viacheslav Petrov,
• Rebecca J. Dooley,
• Alexander A. Marchione,
• Elizabeth L. Diaz,
• Brittany S. Clem and
• William Marshall

Beilstein J. Org. Chem. 2020, 16, 2739–2748, doi:10.3762/bjoc.16.224

• number of important drugs used in different therapeutic areas contain the benzimidazole ring […], such as proton pump inhibitors (omeprazole), antihypertensives (candesartan, telmisartan), antihistaminics (astemizole), antihelmintics (albendazole, mebendazole), as well as several other kinds of still

Reactions of 2-carbonyl- and 2-hydroxy(or methoxy)alkyl-substituted benzimidazoles with arenes in the superacid CF₃SO₃H. NMR and DFT studies of dicationic electrophilic species

• Dmitry S. Ryabukhin,
• Alexey N. Turdakov,
• Natalia S. Soldatova,
• Mikhail O. Kompanets,
• Alexander Yu. Ivanov,
• Irina A. Boyarskaya and
• Aleksander V. Vasilyev

Beilstein J. Org. Chem. 2019, 15, 1962–1973, doi:10.3762/bjoc.15.191

• biological activities including antiparasitic (albendazole, mebendazole), antiulcer (omeprazole), antihypertensive (candesartan, telmisartan, azilsartan, medoxomil, mebefradil), anticancer (bendamustine), antiemetic/antipsychotic (droperidole), antihistaminic (astemizole, emedastine) and many others (Figure

Cyclodextrin-based nanosponges as drug carriers

• Francesco Trotta,
• Marco Zanetti and
• Roberta Cavalli

Beilstein J. Org. Chem. 2012, 8, 2091–2099, doi:10.3762/bjoc.8.235

• was increased about 3-fold after the administration of paclitaxel-loaded nanosponges, in comparison to the control [46]. More recently, Rao et al. studied the influence of carbonate nanosponges on telmisartan, an antihypertensive BCS class II drug characterised by an estimated solubility in water of

• just 9.9 μg/ml resulting in low bioavailability. The formation of a ternary complex of telmisartan with nanosponges and NaHCO3 was seen to synergistically enhance the dissolution rate of telmisartan [47]. Topical delivery systems Nanosponges can be used in gels or creams for topical application. In one

An overview of the key routes to the best selling 5-membered ring heterocyclic pharmaceuticals

• Marcus Baumann,
• Ian R. Baxendale,
• Steven V. Ley and
• Nikzad Nikbin

Beilstein J. Org. Chem. 2011, 7, 442–495, doi:10.3762/bjoc.7.57

• diaminobenzoates was obtained (Scheme 42) [64]. Telmisartan (217, Micardis) is a well known angiotensin II receptor antagonist used in the treatment of hypertension and, heart and bladder diseases. Its pharmacophore consists of two linked benzimidazoles and a biphenyl unit (Scheme 43). As shown previously, such

• benzimidazoles can be formed through the condensation reaction of a 1,2-diaminobenzene and a suitable functionalised carbonyl compound. However, in the case of telmisartan other inherent functionalities such as an ester are present which leads to the formation of several by-products and consequently

• a purity of >99.5% which is by far superior to the previously reported synthesis [65]. Finally, hydrolysis of the methyl ester provides telmisartan in an overall yield of about 50% compared to 21% as previously obtained (Scheme 44). Imidazopyridine Zolpidem (227) is a non-benzodiazepine hypnotic

Efficient and improved synthesis of Telmisartan

• A. Sanjeev Kumar,
• Samir Ghosh and
• G. N. Mehta

Beilstein J. Org. Chem. 2010, 6, No. 25, doi:10.3762/bjoc.6.25

• A. Sanjeev Kumar Samir Ghosh G. N. Mehta Applied Chemistry Department, Sardar Vallabhbhai National Institute of Technology, Surat-395 007, India 10.3762/bjoc.6.25 Abstract An efficient synthesis of the angiotensin II receptor antagonist Telmisartan (1) is presented involving a cross coupling of 4

• . This methodology overcomes many of drawbacks associated with previously reported syntheses. Keywords: antihypertensive drug; oxazoline hydrolysis; Suzuki coupling; Telmisartan; Introduction Telmisartan (1) is an angiotensin II receptor antagonist useful in the treatment of hypertension, heart

• diseases, heart attack, and bladder diseases [1][2][3]. Telmisartan is currently available in the market as an antihypertensive drug [4] under the brand name of Micardis®. Essential hypertension is a major risk factor in cardiovascular diseases and is responsible for one-third of global deaths. Most