Abstract
Pyrazoles are considered privileged scaffolds in medicinal chemistry. Previous reviews have discussed the importance of pyrazoles and their biological activities; however, few have dealt with the chemistry and the biology of heteroannulated derivatives. Therefore, we focused our attention on recent topics, up until 2020, for the synthesis of pyrazoles, their heteroannulated derivatives, and their applications as biologically active moieties. Moreover, we focused on traditional procedures used in the synthesis of pyrazoles.
Highlights
4,5-Dihydro-1Hdo-mfuinroor[e2a,c3ti-ocn]ipnvyorlaviznog lpeyrdazeorloinvea1t2i8v, earsom2a2t6ic awldeehryedessy3n4,tahnedsaizpyerdidibniyumasaoltne-pot domino reaction inv(cSSaocthahllveyemizmneedge11b10py)0yD[91rA.5a2SBz]Cy.oOnltowhniethseihs1igo2hf8dd, iaiahsrtyoerdmeroosaestlpeiccitriavoliftduyerinoh[Hy22d,O3e-ucsn]p3dye4rr,maazincordolewsaa2vpe2y5ir.rraiddiiantioiun m salt catalyzed by DABCO with high diastereoselectivity in H2O under microwave irradiation (Scheme 110) [152]. 4,5-Dihydro-1H-furo[2,3-c]pyrazole derivatives 226 were synthe domino reaction involving pyrazolone 128, aromatic aldehydes 34, an catalyzed by DABCO with high diastereoselectivity in H2O under mic (Scheme 110) [152]
4,5-Dihydro-1H-furo[2,3-c]pyrazole derivatives 226 were synthesized by a one-p domino reaction involving pyrazolone 128, aromatic aldehydes 34, and a pyridinium s catalyzed by DABCO with high diastereoselectivity in H2O under microw4a7voef 7i1rradiat (Scheme 110) [152]
FFigiguruer1e01. 0S.trSutcrtuucretsuoref ssoomf esoanmtiecaanncteircaacnticveerpaycrtaizvoelepsy5r6a, z6o1ale–sf, 5a6n,d6212a9––f2,36a.nd 229–236. Another pyrazolo-anticancer drug known as Lorlatinib 231 (Figure 10) [156] is an orally available drug known as ATP-competitive inhibitor of the receptor tyrosine kinases, anaplastic lymphoma kinase (ALK), and C-ros oncogene 1 (Ros1), with potential antineoplastic activity
Summary
Can be represented in three tautome Unsubstituted pyrazole can be represented in three tautomeric forms [2] (Figure 2). Unsubstituted pyrazole can be represented in three tautome affiliations. As semiconductors [10], liquid crystals [11], and organic light-emitting diodIensb[i1o2lo].gical aspects, pyrazoles are known to exhibit antibacterial [13], anticancer [14,15], anti-tIunbebrcioulloarg[i1c6a]l, aanstpi-eicntflsa,mpmyraatozroyle[1s7a,1r8e],kanntoidwenprteossaenxth[i1b9i,t20a]n, atinbtaifcutnegriaall[2[11]3, ]a,naxni-ticancer [o1ly4t,i1c5[]2,2a],natni-ttiu-AbIeDrScu[2la3]r, [a1n6d],anatni-tmi-ianlafrlaiaml amctaivtiotrieys [[2147],.1P8y],raaznotliedseaplsroesesxahnibtit[1p9ro,2m0i]s,inagntifunga [a2n1t]io, xaindxainotlyatcitciv[i2ti2e]s, [a2n5t]i,-aAnIaDlgSes[2ic3p],raonpderatinesti[-2m6]a,ltahreiaylbaicntdivtiotieesstr[o2g4e].nPryecreapztoolress[a2l7s]o, exhibi ptohxreoiydmahsiasevienengnzeyaumnroteipo[rx2o9itde],cattnhivteeyapchrtaoivvpeietriateinestsi[h[22e58p]]a,, thaoantvoaexlgitcheietsyiccappproarbpoieplirettyiretosief[sb3i0[n]2d,6ai]nn,gttihtloeeityshhebmminaondniaotloapmerosintpre-ogen re ceertpietos r[s31[]2,7a]n,ttihpreoylihfearvateivneepurroopperrotiteesct[3iv2e], parreoppreerfteirersed[2f8o]r, thisasvuee tnhoenc-sappeacbifiilcitaylkoaflibniending to tphheosmphoantoasaemininheibiotoxridinahseibietniozny[m33e], [a2c9t]a,stchyecylinh-advepeeanndteinhtekpiantaosteoixnihciibtyitoprsro[3p4e]r, thiaevse[30], antainletii-shhympearngilaylcepmroicpperotipeesr[ti3e1s][,3a5n],tiapnrtio-lniifterricatoixviedeprsyonptehratsies ([N32O],Sas)re[3p6]r,ehfearvreeidmfmorutnios-sue non spupecpirfeiscsanlktaplrionpeeprthieoss[p3h7]a,taansde dinehmiobnitsotraitnehinibseitcitoicnid[a3l3a]c,taivcittiaes [c3y8c]l.in-dependent kinase inhibitPoyrsra[z3o4le],shaarevfereaqnutei-nhtlyypoebrsgelryvceedmasicbpioraocptievreticeosm[p3o5n],eanntstiin-nciotrmicmoexrcidiaellysyanvtahilaasbeles CIbnaentchboismeccbooinnmteedbxtiw,nmeitdhanwmyiemtthaelmt-hcaoetdtaasllya-zcdeaddtra,elosyrsgzaaetndoom, -oceragctaoalnnyozome-dcya, talyzed (f“lgorweecnh”e) manidstmryu,latin-cdomotphoenremntertehaocdtiso.nIsn. this context, many methods address atom economy (“green”) and multi-component reactions
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