Synthesis and Biological Evaluation of New Hydrazone Derivatives of Quinoline and Their Cu(II) and Zn(II) Complexes against <i>Mycobacterium tuberculosis</i>

<table class="table-group" id="tab5"><tr><td><table class="table"><tr><td class="thead-hr" colspan="6"><hr/></td></tr><tr class="thead"><td align="left">Compounds</td><td align="center">Phenolic <svg height="10.549pt" id="M12" style="vertical-align:-4.54895pt" version="1.1" viewbox="-0.0498162 -6.00005 27.1923 10.549" width="27.1923pt" xmlns="http://www.w3.org/2000/svg" xmlns:xlink="http://www.w3.org/1999/xlink"><g transform="matrix(.013,0,0,-0.013,0,0)"><path d="M469 334C469 405 442 451 408 451C394 451 379 443 373 437L374 430C384 414 395 372 395 317C395 163 317 47 226 47C173 47 142 84 163 185C169 214 181 265 200 334C208 363 211 386 211 404C211 437 199 451 176 451C124 451 64 404 24 348L44 320C86 366 113 382 121 382C132 382 130 371 122 341C102 266 88 204 80 164C76 143 72 121 72 107C72 23 131 -12 188 -12C327 -12 469 174 469 334Z" id="g50-242"></path><glyph.data ascent="3443" descent="-2856" horiz-adv-x="493" vert-adv-y="493"></glyph.data></g><g transform="matrix(.0091,0,0,-0.0091,6.084,3.001)"><path d="M309 -142C211 -61 151 99 151 271S210 601 309 683L288 710C141 611 75 451 75 272V271C75 90 141 -72 288 -169L309 -142Z" id="g50-41"></path><glyph.data ascent="3443" descent="-2856" horiz-adv-x="358" vert-adv-y="358"></glyph.data></g><g transform="matrix(.0091,0,0,-0.0091,9.342,3.001)"><path d="M387 665C175 665 46 498 46 318C46 123 194 -15 374 -15C558 -15 712 114 712 333C712 535 557 665 387 665ZM364 625C495 625 607 518 607 306C607 115 505 25 396 25C256 25 151 161 151 346C151 532 255 625 364 625Z" id="g58-77"></path><glyph.data ascent="1007" descent="-369" horiz-adv-x="757" vert-adv-y="757"></glyph.data></g><g transform="matrix(.0091,0,0,-0.0091,16.166,3.001)"><path d="M738 650H471V617C551 612 559 606 559 524V368H218V524C218 606 227 612 305 617V650H38V617C123 612 131 606 131 524V126C131 44 124 38 41 33V0H310V33C226 38 218 44 218 126V321H559V126C559 44 551 38 463 33V0H737V33C654 38 646 44 646 126V524C646 606 654 612 738 617V650Z" id="g58-70"></path><glyph.data ascent="1007" descent="-369" horiz-adv-x="777" vert-adv-y="777"></glyph.data></g><g transform="matrix(.0091,0,0,-0.0091,23.237,3.001)"><path d="M283 271C283 451 220 610 70 710L48 683C146 603 207 443 207 271S149 -59 48 -142L70 -169C220 -67 283 90 283 271Z" id="g50-42"></path><glyph.data ascent="3443" descent="-2856" horiz-adv-x="358" vert-adv-y="358"></glyph.data></g></svg> <br/>Cm<sup>−1</sup></td><td align="center">Amide <svg height="10.549pt" id="M13" style="vertical-align:-4.54895pt" version="1.1" viewbox="-0.0498162 -6.00005 31.8872 10.549" width="31.8872pt" xmlns="http://www.w3.org/2000/svg" xmlns:xlink="http://www.w3.org/1999/xlink"><g transform="matrix(.013,0,0,-0.013,0,0)"><path d="M469 334C469 405 442 451 408 451C394 451 379 443 373 437L374 430C384 414 395 372 395 317C395 163 317 47 226 47C173 47 142 84 163 185C169 214 181 265 200 334C208 363 211 386 211 404C211 437 199 451 176 451C124 451 64 404 24 348L44 320C86 366 113 382 121 382C132 382 130 371 122 341C102 266 88 204 80 164C76 143 72 121 72 107C72 23 131 -12 188 -12C327 -12 469 174 469 334Z" id="g50-242"></path><glyph.data ascent="3443" descent="-2856" horiz-adv-x="493" vert-adv-y="493"></glyph.data></g><g transform="matrix(.0091,0,0,-0.0091,6.084,3.001)"><path d="M309 -142C211 -61 151 99 151 271S210 601 309 683L288 710C141 611 75 451 75 272V271C75 90 141 -72 288 -169L309 -142Z" id="g50-41"></path><glyph.data ascent="3443" descent="-2856" horiz-adv-x="358" vert-adv-y="358"></glyph.data></g><g transform="matrix(.0091,0,0,-0.0091,9.342,3.001)"><path d="M618 181C565 77 513 26 413 26C264 26 151 150 151 336C151 486 240 625 407 625C516 625 573 582 600 475L634 483C627 540 622 581 613 638C585 643 518 665 435 665C211 665 46 526 46 315C46 158 157 -15 406 -15C480 -15 564 4 594 12C612 43 638 121 651 168L618 181Z" id="g58-65"></path><glyph.data ascent="1007" descent="-369" horiz-adv-x="673" vert-adv-y="673"></glyph.data></g><g transform="matrix(.0091,0,0,-0.0091,15.466,3.001)"><path d="M556 331V384H55V331H556ZM556 140V193H55V140H556Z" id="g54-34"></path><glyph.data ascent="3443" descent="-2856" horiz-adv-x="611" vert-adv-y="611"></glyph.data></g><g transform="matrix(.0091,0,0,-0.0091,21.026,3.001)"><path d="M387 665C175 665 46 498 46 318C46 123 194 -15 374 -15C558 -15 712 114 712 333C712 535 557 665 387 665ZM364 625C495 625 607 518 607 306C607 115 505 25 396 25C256 25 151 161 151 346C151 532 255 625 364 625Z" id="g58-77"></path><glyph.data ascent="1007" descent="-369" horiz-adv-x="757" vert-adv-y="757"></glyph.data></g><g transform="matrix(.0091,0,0,-0.0091,27.915,3.001)"><path d="M283 271C283 451 220 610 70 710L48 683C146 603 207 443 207 271S149 -59 48 -142L70 -169C220 -67 283 90 283 271Z" id="g50-42"></path><glyph.data ascent="3443" descent="-2856" horiz-adv-x="358" vert-adv-y="358"></glyph.data></g></svg> <br/>Cm<sup>−1</sup></td><td align="center">Imine <svg height="10.549pt" id="M14" style="vertical-align:-4.54895pt" version="1.1" viewbox="-0.0498162 -6.00005 31.8598 10.549" width="31.8598pt" xmlns="http://www.w3.org/2000/svg" xmlns:xlink="http://www.w3.org/1999/xlink"><g transform="matrix(.013,0,0,-0.013,0,0)"><path d="M469 334C469 405 442 451 408 451C394 451 379 443 373 437L374 430C384 414 395 372 395 317C395 163 317 47 226 47C173 47 142 84 163 185C169 214 181 265 200 334C208 363 211 386 211 404C211 437 199 451 176 451C124 451 64 404 24 348L44 320C86 366 113 382 121 382C132 382 130 371 122 341C102 266 88 204 80 164C76 143 72 121 72 107C72 23 131 -12 188 -12C327 -12 469 174 469 334Z" id="g50-242"></path><glyph.data ascent="3443" descent="-2856" horiz-adv-x="493" vert-adv-y="493"></glyph.data></g><g transform="matrix(.0091,0,0,-0.0091,6.084,3.001)"><path d="M309 -142C211 -61 151 99 151 271S210 601 309 683L288 710C141 611 75 451 75 272V271C75 90 141 -72 288 -169L309 -142Z" id="g50-41"></path><glyph.data ascent="3443" descent="-2856" horiz-adv-x="358" vert-adv-y="358"></glyph.data></g><g transform="matrix(.0091,0,0,-0.0091,9.342,3.001)"><path d="M618 181C565 77 513 26 413 26C264 26 151 150 151 336C151 486 240 625 407 625C516 625 573 582 600 475L634 483C627 540 622 581 613 638C585 643 518 665 435 665C211 665 46 526 46 315C46 158 157 -15 406 -15C480 -15 564 4 594 12C612 43 638 121 651 168L618 181Z" id="g58-65"></path><glyph.data ascent="1007" descent="-369" horiz-adv-x="673" vert-adv-y="673"></glyph.data></g><g transform="matrix(.0091,0,0,-0.0091,15.466,3.001)"><path d="M556 331V384H55V331H556ZM556 140V193H55V140H556Z" id="g54-34"></path><glyph.data ascent="3443" descent="-2856" horiz-adv-x="611" vert-adv-y="611"></glyph.data></g><g transform="matrix(.0091,0,0,-0.0091,21.026,3.001)"><path d="M731 650H485V618C556 614 580 601 585 558C588 530 592 485 592 390V153H589L173 650H22V618C69 614 92 606 112 582C131 558 132 555 132 483V266C132 175 129 128 125 96C120 49 95 36 36 33V0H281V33C212 36 188 50 183 98C180 129 177 175 177 266V510H179L603 -9H638V390C638 483 640 530 644 561C649 602 674 615 731 618V650Z" id="g58-76"></path><glyph.data ascent="1007" descent="-369" horiz-adv-x="754" vert-adv-y="754"></glyph.data></g><g transform="matrix(.0091,0,0,-0.0091,27.888,3.001)"><path d="M283 271C283 451 220 610 70 710L48 683C146 603 207 443 207 271S149 -59 48 -142L70 -169C220 -67 283 90 283 271Z" id="g50-42"></path><glyph.data ascent="3443" descent="-2856" horiz-adv-x="358" vert-adv-y="358"></glyph.data></g></svg> <br/>Cm<sup>−1</sup></td><td align="center">Phenolic <svg height="10.549pt" id="M15" style="vertical-align:-4.54895pt" version="1.1" viewbox="-0.0498162 -6.00005 29.558 10.549" width="29.558pt" xmlns="http://www.w3.org/2000/svg" xmlns:xlink="http://www.w3.org/1999/xlink"><g transform="matrix(.013,0,0,-0.013,0,0)"><path d="M469 334C469 405 442 451 408 451C394 451 379 443 373 437L374 430C384 414 395 372 395 317C395 163 317 47 226 47C173 47 142 84 163 185C169 214 181 265 200 334C208 363 211 386 211 404C211 437 199 451 176 451C124 451 64 404 24 348L44 320C86 366 113 382 121 382C132 382 130 371 122 341C102 266 88 204 80 164C76 143 72 121 72 107C72 23 131 -12 188 -12C327 -12 469 174 469 334Z" id="g50-242"></path><glyph.data ascent="3443" descent="-2856" horiz-adv-x="493" vert-adv-y="493"></glyph.data></g><g transform="matrix(.0091,0,0,-0.0091,6.084,3.001)"><path d="M309 -142C211 -61 151 99 151 271S210 601 309 683L288 710C141 611 75 451 75 272V271C75 90 141 -72 288 -169L309 -142Z" id="g50-41"></path><glyph.data ascent="3443" descent="-2856" horiz-adv-x="358" vert-adv-y="358"></glyph.data></g><g transform="matrix(.0091,0,0,-0.0091,9.342,3.001)"><path d="M618 181C565 77 513 26 413 26C264 26 151 150 151 336C151 486 240 625 407 625C516 625 573 582 600 475L634 483C627 540 622 581 613 638C585 643 518 665 435 665C211 665 46 526 46 315C46 158 157 -15 406 -15C480 -15 564 4 594 12C612 43 638 121 651 168L618 181Z" id="g58-65"></path><glyph.data ascent="1007" descent="-369" horiz-adv-x="673" vert-adv-y="673"></glyph.data></g><g transform="matrix(.0091,0,0,-0.0091,15.466,3.001)"><path d="M300 253H71L57 198H286L300 253Z" id="g190-46"></path><glyph.data ascent="989" descent="-360" horiz-adv-x="356" vert-adv-y="356"></glyph.data></g><g transform="matrix(.0091,0,0,-0.0091,18.718,3.001)"><path d="M387 665C175 665 46 498 46 318C46 123 194 -15 374 -15C558 -15 712 114 712 333C712 535 557 665 387 665ZM364 625C495 625 607 518 607 306C607 115 505 25 396 25C256 25 151 161 151 346C151 532 255 625 364 625Z" id="g58-77"></path><glyph.data ascent="1007" descent="-369" horiz-adv-x="757" vert-adv-y="757"></glyph.data></g><g transform="matrix(.0091,0,0,-0.0091,25.606,3.001)"><path d="M283 271C283 451 220 610 70 710L48 683C146 603 207 443 207 271S149 -59 48 -142L70 -169C220 -67 283 90 283 271Z" id="g50-42"></path><glyph.data ascent="3443" descent="-2856" horiz-adv-x="358" vert-adv-y="358"></glyph.data></g></svg> <br/>Cm<sup>−1</sup></td><td align="center"><svg height="10.549pt" id="M16" style="vertical-align:-4.54895pt" version="1.1" viewbox="-0.0498162 -6.00005 27.5759 10.549" width="27.5759pt" xmlns="http://www.w3.org/2000/svg" xmlns:xlink="http://www.w3.org/1999/xlink"><g transform="matrix(.013,0,0,-0.013,0,0)"><path d="M469 334C469 405 442 451 408 451C394 451 379 443 373 437L374 430C384 414 395 372 395 317C395 163 317 47 226 47C173 47 142 84 163 185C169 214 181 265 200 334C208 363 211 386 211 404C211 437 199 451 176 451C124 451 64 404 24 348L44 320C86 366 113 382 121 382C132 382 130 371 122 341C102 266 88 204 80 164C76 143 72 121 72 107C72 23 131 -12 188 -12C327 -12 469 174 469 334Z" id="g50-242"></path><glyph.data ascent="3443" descent="-2856" horiz-adv-x="493" vert-adv-y="493"></glyph.data></g><g transform="matrix(.0091,0,0,-0.0091,6.084,3.001)"><path d="M309 -142C211 -61 151 99 151 271S210 601 309 683L288 710C141 611 75 451 75 272V271C75 90 141 -72 288 -169L309 -142Z" id="g50-41"></path><glyph.data ascent="3443" descent="-2856" horiz-adv-x="358" vert-adv-y="358"></glyph.data></g><g transform="matrix(.0091,0,0,-0.0091,9.342,3.001)"><path d="M618 181C565 77 513 26 413 26C264 26 151 150 151 336C151 486 240 625 407 625C516 625 573 582 600 475L634 483C627 540 622 581 613 638C585 643 518 665 435 665C211 665 46 526 46 315C46 158 157 -15 406 -15C480 -15 564 4 594 12C612 43 638 121 651 168L618 181Z" id="g58-65"></path><glyph.data ascent="1007" descent="-369" horiz-adv-x="673" vert-adv-y="673"></glyph.data></g><g transform="matrix(.0091,0,0,-0.0091,15.466,3.001)"><path d="M300 253H71L57 198H286L300 253Z" id="g190-46"></path><glyph.data ascent="989" descent="-360" horiz-adv-x="356" vert-adv-y="356"></glyph.data></g><g transform="matrix(.0091,0,0,-0.0091,18.718,3.001)"><path d="M502 500C497 551 492 613 491 650H43V617C122 612 130 606 130 521V129C130 45 122 38 41 33V0H319V33C227 38 217 45 217 129V305H319C411 305 413 295 427 225H461V421H427C414 357 411 348 319 348H217V580C217 609 219 612 250 612H330C401 612 423 605 439 578C452 557 458 539 467 496L502 500Z" id="g58-68"></path><glyph.data ascent="1007" descent="-369" horiz-adv-x="540" vert-adv-y="540"></glyph.data></g><g transform="matrix(.0091,0,0,-0.0091,23.632,3.001)"><path d="M283 271C283 451 220 610 70 710L48 683C146 603 207 443 207 271S149 -59 48 -142L70 -169C220 -67 283 90 283 271Z" id="g50-42"></path><glyph.data ascent="3443" descent="-2856" horiz-adv-x="358" vert-adv-y="358"></glyph.data></g></svg> <br/>Cm<sup>−1</sup></td></tr><tr><td class="thead-hr" colspan="6"><hr/></td></tr><tr><td align="left">2a</td><td align="center">3208</td><td align="center">1660</td><td align="center">1625</td><td align="center">1425</td><td align="center">1294</td></tr><tr><td align="left">2b</td><td align="center">3488</td><td align="center">1650</td><td align="center">1630</td><td align="center">1427</td><td align="center">1288</td></tr><tr><td align="left">2c</td><td align="center">3444</td><td align="center">1662</td><td align="center">1628</td><td align="center">1438</td><td align="center">1234</td></tr><tr><td align="left">2d</td><td align="center">3538</td><td align="center">1656</td><td align="center">1627</td><td align="center">1425</td><td align="center">1263</td></tr><tr><td align="left">2e</td><td align="center">3193</td><td align="center">1668</td><td align="center">1625</td><td align="center">1428</td><td align="center">1232</td></tr><tr class="table-tr"><td colspan="6"><hr class="tbody-hr"/></td></tr></table></td></tr></table>

FTIR bands for hydrazones (2a–2e) and their assignments.

Bioinorganic Chemistry and Applications

tab5

Table 5

Table 5: Synthesis and Biological Evaluation of New Hydrazone Derivatives of Quinoline and Their Cu(II) and Zn(II) Complexes against <i>Mycobacterium tuberculosis</i> 

Table 5 | Synthesis and Biological Evaluation of New Hydrazone Derivatives of Quinoline and Their Cu(II) and Zn(II) Complexes against Mycobacterium tuberculosis 