ethyl (2-chloro-4-propionylphenoxy)acetate | 80762-29-4

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: ethyl (2-chloro-4-propionylphenoxy)acetate
• 英文别名: ethyl 2-(2-chloro-4-propionylphenoxy) acetate；ethyl 2-(2-chloro-4-propionylphenoxy)-acetate；Ethyl-2-(2-chloro-4-propionylphenoxy)acetate；ethyl 2-(2-chloro-4-propanoylphenoxy)acetate
• CAS: 80762-29-4
• 化学式: C₁₃H₁₅ClO₄
• 分子量: 270.713
• InChiKey: OFENBYKFCXHNON-UHFFFAOYSA-N

物化性质

• 熔点：
  125-126.5 °C(Solv: ethanol (64-17-5))
• 沸点：
  387.0±32.0 °C(Predicted)
• 密度：
  1.195±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3
• 重原子数：
  18
• 可旋转键数：
  7
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  52.6
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  ethyl (2-chloro-4-propionylphenoxy)acetate 生成 methyl 2-[2-chloro-4-(2-bromopropionyl)phenoxy]acetate
  参考文献：
  名称：

  MEHTA, N. B.

  摘要：

  DOI：
• 作为产物：
  描述：

  2-氯苯甲醚 在 三氯化铝 、 potassium tert-butylate 、 potassium iodide 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 6.0h， 生成 ethyl (2-chloro-4-propionylphenoxy)acetate
  参考文献：
  名称：

  A New Lead for Nonpeptidic Active-Site-Directed Inhibitors of the Severe Acute Respiratory Syndrome Coronavirus Main Protease Discovered by a Combination of Screening and Docking Methods

  摘要：

  The coronavirus main protease, M-pro, is considered to be a major target for drugs suitable for combating coronavirus infections including severe acute respiratory syndrome (SARS). An HPLC-based screening of electrophilic compounds that was performed to identify potential M-pro inhibitors revealed etacrynic acid tert-butylamide (6a) as an effective nonpeptidic inhibitor. Docking studies suggested a binding mode in which the phenyl ring acts as a spacer bridging the inhibitor's activated double bond and its hydrophobic tert-butyl moiety. The latter is supposed to fit into the S4 pocket of the target protease. Furthermore, these studies revealed etacrynic acid amide (6b) as a promising lead for nonpeptidic active-site-directed M-pro inhibitors. In a fluorimetric enzyme assay using a novel fluorescence resonance energy transfer (FRET) pair labeled substrate, compound 6b showed a K-i value of 35.3 mu M. Since the novel lead compound does not target the S1', S1, and S2 subsites of the enzyme's substrate-binding pockets, there is room for improvement that underlines the lead character of compound 6b.

  DOI：

  10.1021/jm0501782

文献信息

• Compounds and methods of making same
  申请人：Burroughs Wellcome Co.

  公开号：US04347176A1

  公开（公告）日：1982-08-31

  A radioimmunoassay procedure has been discovered for bupropion [(.+-.)-2-t-butylamino-3-chloropropiophenone], an antidepressant compound, in biological fluids. Novel compounds of formula ##STR1## wherein either R.sub.2 is oxygen and R.sub.1 is (CH.sub.2).sub.n --0--(CO).sub.m --(CH.sub.2).sub.p --COOH where n is an integer from 0 to 5, m is 0 or 1, and p is an integer from 1 to 4; or R.sub.1 is hydrogen and R.sub.2 is N--0--(CH.sub.2).sub.q --COOH where q is an integer from 1 to 3, and novel methods of making them and novel intermediates useful therein are disclosed. Novel immunogens for raising bupropion specific antisera, and novel methods of making them are disclosed comprising conjugates of the novel compounds and suitable carrier material. The drug is added to the antisera together with novel radiolabeled competitor of formula ##STR2## wherein R' is a suitable radioisotope as described above and R.sub.3 is hydrogen, R.sub.4 is Cl, and R.sub.5 is oxygen, or R' is hydrogen and either (a) R.sub.3 is H and R.sub.4 is Cl and R.sub.5 is NO(CH.sub.2).sub.q CO--X where q is as defined for formula I and X is a group having formula III ##STR3## wherein R.sub.6 is a suitable radioisotope as described above, R.sub.7 is hydroxyl, and s is an integer from 1 to 4; (b) R.sub.4 is Cl, R.sub.5 is oxygen, and R.sub.3 is (CH.sub.2).sub.n --0--(CO).sub.m --(CH.sub.2).sub.p --CO--X where n, m, and p are as defined for formula I and X is as defined above; or (c) R.sub.3 is hydroxy, R.sub.5 is oxygen and R.sub.4 is a suitable radioisotope as defined above. The measure of radioactivity of the antisera bound radiolabeled competitor provides a measure of the amount of drug in the assayed biological fluid sample. A standard curve can be constructed from which the amount of drug in the assay sample can be interpolated. A kit is disclosed for practicing the radioimmunoassay.

  已发现了一种用于生物液体中抗抑郁化合物丙酮莫林[(.+-.)-2-t-丁基氨基-3-氯丙酮]的放射免疫分析程序。公开了一系列新颖化合物的公式，其中R.sub.2为氧，R.sub.1为(CH.sub.2).sub.n--0--(CO).sub.m--(CH.sub.2).sub.p--COOH，其中n为0至5的整数，m为0或1，p为1至4的整数；或者R.sub.1为氢，R.sub.2为N--0--(CH.sub.2).sub.q--COOH，其中q为1至3的整数，并公开了制备它们以及其中有用的新颖中间体的新方法。公开了用于产生丙酮莫林特异抗血清的新免疫原以及制备它们的新方法，其中包括新化合物和适当载体材料的结合物。药物与新的放射标记竞争物质一起加入到抗血清中，该竞争物质的公式为##STR2##，其中R'是如上所述的适当放射性同位素，R.sub.3是氢，R.sub.4是氯，R.sub.5是氧，或者R'是氢，且(a)R.sub.3是H，R.sub.4是Cl，R.sub.5是NO(CH.sub.2).sub.qCO--X，其中q如公式I所定义，X是具有公式III的基团##STR3##，其中R.sub.6是如上所述的适当放射性同位素，R.sub.7是羟基，s是1至4的整数；(b)R.sub.4是Cl，R.sub.5是氧，R.sub.3是(CH.sub.2).sub.n--0--(CO).sub.m--(CH.sub.2).sub.p--CO--X，其中n，m和p如公式I所定义，X如上所定义；或者(c)R.sub.3是羟基，R.sub.5是氧，R.sub.4是如上所定义的适当放射性同位素。抗血清结合的放射标记竞争物的放射活性测量提供了测定生物液体样品中药物量的测量值。可以从标准曲线中构建出药物在测定样品中的量。公开了用于进行放射免疫分析的试剂盒。
• Compounds and methods of making them
  申请人：Burroughs Wellcome Co.

  公开号：US04347177A1

  公开（公告）日：1982-08-31

  A radioimmunoassay procedure has been discovered for bupropion [(.+-.)-2-t-butylamino-3-chloropropiophenone], an antidepressant compound, in biological fluids. Novel compounds of formula ##STR1## wherein either R.sub.2 is oxygen and R.sub.1 is (CH.sub.2).sub.n --O--(CO).sub.m --(CH.sub.2).sub.p --COOH where n is an integer from 0 to 5, m is 0 or 1, and p is an integer from 1 to 4; or R.sub.1 is hydrogen and R.sub.2 is N--O--(CH.sub.2).sub.q --COOH where q is an integer from 1 to 3, and novel methods of making them and novel intermediates useful therein are disclosed. Novel immunogens for raising bupropion specific antisera, and novel methods of making them are disclosed comprising conjugates of the novel compounds and suitable carrier material. The drug is added to the antisera together with novel radiolabeled competitor of formula ##STR2## wherein R' is a suitable radioisotope as described above and R.sub.3 is hydrogen, R.sub.4 is Cl, and R.sub.5 is oxygen, or R' is hydrogen and either (a) R.sub.3 is H and R.sub.4 is Cl and R.sub.5 is NO(CH.sub.2).sub.q CO--X where q is as defined for formula I and X is a group having formula III ##STR3## wherein R.sub.6 is a suitable radioisotope as described above, R.sub.7 is hydroxyl, and s is an integer from 1 to 4; (b) R.sub.4 is Cl, R.sub.5 is oxygen, and R.sub.3 is (CH.sub.2).sub.n --O--(CO).sub.m --(CH.sub.2).sub.p --CO--X where n, m, and p are as defined for formula I and X is as defined above; or (c) R.sub.3 is hydroxy, R.sub.5 is oxygen and R.sub.4 is a suitable radioisotope as defined above. The measure of radioactivity of the antisera bound radiolabeled competitor provides a measure of the amount of drug in the assayed biological fluid sample. A standard curve can be constructed from which the amount of drug in the assay sample can be interpolated. A kit is disclosed for practicing the radioimmunoassay.

  一种用于在生物液体中检测抗抑郁化合物丁腈羟考酮的放射免疫分析方法已被发现。其中一些新化合物的公式为##STR1## 其中R.sub.2为氧，R.sub.1为(CH.sub.2).sub.n --O--(CO).sub.m --(CH.sub.2).sub.p --COOH，其中n为0至5的整数，m为0或1，p为1至4的整数；或者R.sub.1为氢，R.sub.2为N--O--(CH.sub.2).sub.q --COOH，其中q为1至3的整数。还揭示了制备这些新化合物的新方法和有用的新中间体。揭示了用于提高丁腈羟考酮特异性抗血清的新免疫原和制备它们的新方法，包括新化合物和适当载体材料的结合物。将药物与放射性标记的竞争物质一起加入抗血清中，所述竞争物质的公式为##STR2## 其中R'为适当的放射性同位素，R.sub.3为氢，R.sub.4为氯，R.sub.5为氧，或者R'为氢，且(a)R.sub.3为H，R.sub.4为Cl，R.sub.5为NO(CH.sub.2).sub.q CO--X，其中q如公式I所定义，X为具有公式III的基团##STR3## 其中R.sub.6为适当的放射性同位素，R.sub.7为羟基，s为1至4的整数；(b)R.sub.4为Cl，R.sub.5为氧，R.sub.3为(CH.sub.2).sub.n --O--(CO).sub.m --(CH.sub.2).sub.p --CO--X，其中n，m和p如公式I所定义，X如上所述；或(c)R.sub.3为羟基，R.sub.5为氧，R.sub.4为如上所定义的适当放射性同位素。抗血清结合放射性标记竞争物质的放射性测量提供了检测生物液体样品中药物量的测量值。可以从标准曲线中构建插值出检测样品中药物量。还揭示了用于实施放射免疫分析的套件。
• Compounds and methods of making
  申请人：Burroughs Wellcome Co.

  公开号：US04347178A1

  公开（公告）日：1982-08-31

  A radioimmunoassay procedure has been discovered for bupropion [(.+-.)-2-t-butylamino-3-chloropropiophenone], an antidepressant compound, in biological fluids. Novel compounds of formula ##STR1## wherein either R.sub.2 is oxygen and R.sub.1 is (CH.sub.2).sub.n -O-(CO).sub.m -(CH.sub.2).sub.p -COOH where n is an integer from 0 to 5, m is 0 or 1, and p is an integer from 1 to 4; or R.sub.1 is hydrogen and R.sub.2 is N-O-(CH.sub.2).sub.q -COOH where q is an integer from 1 to 3, and novel methods of making them and novel intermediates useful therein are disclosed. Novel immunogens for raising bupropion specific antisera, and novel methods of making them are disclosed comprising conjugates of the novel compounds and suitable carrier material. The drug is added to the antisera together with novel radiolabeled competitor of formula ##STR2## wherein R' is a suitable radioisotope as described above and R.sub.3 is hydrogen, R.sub.4 is Cl, and R.sub.5 is oxygen, or R' is hydrogen and either (a) R.sub.3 is H and R.sub.4 is Cl and R.sub.5 is NO(CH.sub.2).sub.q CO-X where q is as defined for formula I and X is a group having formula III ##STR3## wherein R.sub.6 is a suitable radioisotope as described above, R.sub.7 is hydroxyl, and s is an integer from 1 to 4; (b) R.sub.4 is Cl, R.sub.5 is oxygen, and R.sub.3 is (CH.sub.2).sub.n -O-(CO).sub.m -(CH.sub.2).sub.p -CO-X where n, m, and p are as defined for formula I and X is as defined above; or (c) R.sub.3 is hydroxy, R.sub.5 is oxygen and R.sub.4 is a suitable radioisotope as defined above. The measure of radioactivity of the antisera bound radiolabeled competitor provides a measure of the amount of drug in the assayed biological fluid sample. A standard curve can be constructed from which the amount of drug in the assay sample can be interpolated. A kit is disclosed for practicing the radioimmunoassay.

  已经发现了一种用于生物液体中抗抑郁化合物丙吡胺[(.+-.)-2-t-叔丁基氨基-3-氯代丙酮]的放射免疫测定程序。公开了公式##STR1##的新化合物，其中R.sub.2为氧，R.sub.1为(CH.sub.2).sub.n -O-(CO).sub.m -(CH.sub.2).sub.p -COOH，其中n为0至5的整数，m为0或1，p为1至4的整数; 或者R.sub.1为氢，R.sub.2为N-O-(CH.sub.2).sub.q -COOH，其中q为1至3的整数，公开了制造它们的新方法和有用的新中间体。公开了用于提高丙吡胺特异性抗血清的新免疫原和制造它们的新方法，包括新化合物和适当的载体材料的结合物。将药物添加到抗血清中，与公式##STR2##的新放射标记竞争剂一起使用，其中R'为上述合适的放射性同位素，R.sub.3为氢，R.sub.4为Cl，R.sub.5为氧，或者R'为氢，且要么(a) R.sub.3为H，R.sub.4为Cl，R.sub.5为NO(CH.sub.2).sub.q CO-X，其中q如公式I所定义，X是具有公式III##STR3##的基团，其中R.sub.6是上述合适的放射性同位素，R.sub.7是羟基，s为1至4的整数; (b) R.sub.4为Cl，R.sub.5为氧，R.sub.3为(CH.sub.2).sub.n -O-(CO).sub.m -(CH.sub.2).sub.p -CO-X，其中n、m和p如公式I所定义，X如上所述; 或者(c) R.sub.3为羟基，R.sub.5为氧，R.sub.4为上述合适的放射性同位素。抗血清结合放射标记竞争剂的放射性测量提供了测定生物液体样品中药物量的测量。可以从标准曲线中构建样品测量中药物量的插值。公开了用于实施放射免疫测定的试剂盒。
• 3.sup.H Labeled compounds
  申请人：Burroughs Wellcome Co.

  公开号：US04347382A1

  公开（公告）日：1982-08-31

  A radioimmunoassay procedure has been discovered for bupropion [(.+-.)-2-t-butylamino-3-chloropropiophenone], an antidepressant compound, in biological fluids. Novel compounds of formula ##STR1## wherein either R.sub.2 is oxygen and R.sub.1 is (CH.sub.2).sub.n -0-(CO).sub.m -(CH.sub.2).sub.p -COOH where n is an integer from 0 to 5, m is 0 or 1, and p is an integer from 1 to 4; or R.sub.1 is hydrogen and R.sub.2 is N-O-(CH.sub.2).sub.q -COOH where q is an integer from 1 to 3, and novel methods of making them and novel intermediates useful therein are disclosed. Novel immunogens for raising bupropion specific antisera, and novel methods of making them are disclosed comprising conjugates of the novel compounds and suitable carrier material. The drug is added to the antisera together with novel radiolabeled competitor of formula ##STR2## wherein R' is a suitable radioisotope as described above and R.sub.3 is hydrogen, R.sub.4 is CL, and R.sub.5 is oxygen, or R' is hydrogen and either (a) R.sub.3 is H and R.sub.4 is Cl and R.sub.5 is NC(CH.sub.2).sub.q CO-X where q is as defined for formula I and X is a group having formula III ##STR3## wherein R.sub.6 is a suitable radioisotope as described above, R.sub.7 is hydroxyl, and s is an integer from 1 to 4; (b) R.sub.4 is Cl, R.sub.5 is oxygen, and R.sub.3 is (CH.sub.2).sub.n -0-(CO).sub.m -(CH.sub.2).sub.p -CO-X where n, m, and p are as defined for formula I and X is as defined above; or (c) R.sub.3 is hydroxy, R.sub.5 is oxygen and R.sub.4 is a suitable radioisotope as defined above. The measure of radioactivity of the antisera bound radiolabeled competitor provides a measure of the amount of drug in the assayed biological fluid sample. A standard curve can be constructed from which the amount of drug in the assay sample can be interpolated. A kit is disclosed for practicing the radioimmunoassay.

  一种用于生物液体中抗抑郁化合物bupropion [(+/-)-2-t-丁基氨基-3-氯代丙酮]的放射免疫测定程序已被发现。公开了新的化合物的公式，其中R.sub.2为氧，R.sub.1为(CH.sub.2).sub.n-0-(CO).sub.m-(CH.sub.2).sub.p-COOH，其中n为0到5的整数，m为0或1，p为1到4的整数；或R.sub.1为氢，R.sub.2为N-O-(CH.sub.2).sub.q-COOH，其中q为1到3的整数，并公开了制备它们的新方法和有用的新中间体。公开了用于提高bupropion特异性抗血清的新免疫原和制备它们的新方法，其中包括新化合物和适当载体材料的结合物。将药物加入抗血清中，与公式中的新放射性标记竞争物一起，其中R'是适当的放射性同位素，如上述所述，R.sub.3是氢，R.sub.4是CL，R.sub.5是氧，或R'是氢，且（a）R.sub.3为H，R.sub.4为Cl，R.sub.5为NC(CH.sub.2).sub.qCO-X，其中q如公式I所定义，X是具有公式III的组，其中R.sub.6是适当的放射性同位素，如上述所述，R.sub.7是羟基，s是1到4的整数；（b）R.sub.4为Cl，R.sub.5为氧，R.sub.3为（CH.sub.2).sub.n-0-(CO).sub.m-(CH.sub.2).sub.p-CO-X，其中n、m和p如公式I所定义，X如上所述；或（c）R.sub.3为羟基，R.sub.5为氧，R.sub.4是上述所定义的适当的放射性同位素。抗血清结合的放射标记竞争物的放射性测量提供了测定生物液体样品中药物量的测量。可以从标准曲线中构建出药物在测定样品中的量。公开了用于实施放射免疫测定的试剂盒。
• Radioactive nuclide labeled propiophenone compounds
  申请人：Burroughs Wellcome Co.

  公开号：US04355179A1

  公开（公告）日：1982-10-19

  A radioimmunoassay procedure has been discovered for bupropion [(.+-.)-2-t-butylamino-3-chloropropiophenone], an antidepressant compound, in biological fluids. Novel compounds of formula ##STR1## wherein either R.sub.2 is oxygen and R.sub.1 is (CH.sub.2).sub.n --O--(CO).sub.m --(CH.sub.2).sub.p --COOH where n is an integer from 0 to 5, m is 0 or 1, and p is an integer from 1 to 4; or R.sub.1 is hydrogen and R.sub.2 is N--O--(CH.sub.2).sub.q --COOH where q is an integer from 1 to 3, and novel methods of making them and novel intermediates useful therein are disclosed. Novel immunogens for raising bupropion specific antisera, and novel methods of making them are disclosed comprising conjugates of the novel compounds and suitable carrier material. The drug is added to the antisera together with novel radiolabeled competitor of formula ##STR2## wherein R' is a suitable radioisotope as described above and R.sub.3 is hydrogen, R.sub.4 is Cl, and R.sub.5 is oxygen, or R' is hydrogen and either (a) R.sub.3 is H and R.sub.4 is Cl and R.sub.5 is NO(CH.sub.2).sub.q CO--X where q is as defined for formula I and X is a group having formula III ##STR3## wherein R.sub.6 is a suitable radioisotope as described above, R.sub.7 is hydroxyl, and s is an integer from 1 to 4; (b) R.sub.4 is Cl, R.sub.5 is oxygen, and R.sub.3 is (CH.sub.2).sub.n --0--(CO).sub.m --(CH.sub.2).sub.p --CO--X where n, m, and p are as defined for formula I and X is as defined above; or (c) R.sub.3 is hydroxy, R.sub.5 is oxygen and R.sub.4 is a suitable radioisotope as defined above. The measure of radioactivity of the antisera bound radiolabeled competitor provides a measure of the amount of drug in the assayed biological fluid sample. A standard curve can be constructed from which the amount of drug in the assay sample can be interpolated. A kit is disclosed for practicing the radioimmunoassay.

  一项放射免疫测定程序已被发现，用于检测生物液中的抗抑郁化合物丙酮酸丁哌酯[(.+-.)-2-t-丁基氨基-3-氯代丙酮酸苯]。本文还披露了新的化合物公式 ##STR1## 在该公式中，R.sub.2 为氧，R.sub.1 为 (CH.sub.2).sub.n --O--(CO).sub.m --(CH.sub.2).sub.p --COOH，其中 n 为0至5的整数，m 为0或1，p 为1至4的整数；或者 R.sub.1 为氢，R.sub.2 为 N--O--(CH.sub.2).sub.q --COOH，其中 q 为1至3的整数，还披露了制备这些新化合物的新方法和有用的新中间体。本文还披露了用于提高丙酮酸丁哌酯特异性抗血清的新免疫原以及制备它们的新方法，其中包括新化合物和适当的载体材料的结合物。将药物添加到抗血清中，与新的放射性标记竞争剂结合，其公式为 ##STR2## 在该公式中，R' 是适当的放射性同位素，如上所述，R.sub.3 是氢，R.sub.4 是氯，R.sub.5 是氧，或者 R' 是氢，且 (a) R.sub.3 是 H，R.sub.4 是 Cl，R.sub.5 是 NO(CH.sub.2).sub.q CO--X，其中 q 如公式 I 中所定义，X 是具有公式 III 的基团 ##STR3## 在该公式中，R.sub.6 是适当的放射性同位素，如上所述，R.sub.7 是羟基，s 是1至4的整数；(b) R.sub.4 是 Cl，R.sub.5 是氧，且 R.sub.3 是 (CH.sub.2).sub.n --0--(CO).sub.m --(CH.sub.2).sub.p --CO--X，其中 n、m 和 p 如公式 I 中所定义，X 如上所述；或者 (c) R.sub.3 是羟基，R.sub.5 是氧，R.sub.4 是适当的放射性同位素，如上所述。抗血清结合放射性标记竞争剂的放射性测量提供了测定生物液样品中药物量的测量值。可以从标准曲线中构建出药物在测定样品中的量。本文还披露了一种用于实施放射免疫测定的试剂盒。