methyl 2,4-dichloro-6-hydroxybenzoate | 1401249-88-4

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: methyl 2,4-dichloro-6-hydroxybenzoate
• CAS: 1401249-88-4
• 化学式: C₈H₆Cl₂O₃
• 分子量: 221.04
• InChiKey: SKXNDSBUOUAYHR-UHFFFAOYSA-N

物化性质

• 沸点：
  276.0±35.0 °C(Predicted)
• 密度：
  1.476±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  13
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  46.5
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  methyl 2,4-dichloro-6-hydroxybenzoate 、 三氟甲磺酸 在 吡啶 作用下， 以 二氯甲烷 为溶剂， 反应 2.0h， 生成 methyl 2,4-dichloro-6-{[(trifluoromethyl)sulfonyl]oxy}benzoate
  参考文献：
  名称：

  [EN] ALPHA-HYDROXY AMIDES AS BRADYKININ ANTAGONISTS OR INVERSE AGONISTS
  [FR] ALPHA-HYDROXY AMIDES UTILISES COMME ANTAGONISTES OU AGONISTES INVERSES DE LA BRADYKININE

  摘要：

  通用公式（I）的α-羟基酰胺衍生物是布雷肯肽B1拮抗剂或逆向激动剂，在治疗或预防与布雷肯肽B1途径相关的疼痛和炎症症状方面很有用。R2a从（1）Ra组中选择。 （2）（CH2）nNRbC（O）Ra。（3）（CH2）nNRbSO2Rd。（4）（CH2）nNRbCO2Ra。（5）（CH2）k-杂环，可选择地取代为1到3个独立选择的卤素，硝基，氰基，ORa，SRa，C1-4烷基和C1-3卤代烷基，其中所述杂环是（a）具有N，O和S中选择的环杂原子的5元杂芳环，并且可选地具有多达3个额外的环氮原子，其中所述环可选地与苯融合；或（b）含有1到3个环氮原子和其N-氧化物的6元杂芳环。其中所述环可选地与苯融合。（6）（CH2）kCO2Ra和（7）（CH2）C（O）NRbRc。 R2b是OH或从R2a选择的组；或R2a和R2b与它们连接的碳原子一起形成一个3到7个成员的碳环，可选择地取代为1到4个独立选择的卤素，ORa，C1-4烷基和C1-4卤代烷基；

  公开号：

  WO2005063690A1
• 作为产物：
  描述：

  甲醇 、 4,6-二氯水杨醛 在 vanadia 高氯酸 、 双氧水 作用下， 以 水 为溶剂， 反应 0.17h， 生成 methyl 2,4-dichloro-6-hydroxybenzoate
  参考文献：
  名称：

  [EN] ALPHA-HYDROXY AMIDES AS BRADYKININ ANTAGONISTS OR INVERSE AGONISTS
  [FR] ALPHA-HYDROXY AMIDES UTILISES COMME ANTAGONISTES OU AGONISTES INVERSES DE LA BRADYKININE

  摘要：

  通用公式（I）的α-羟基酰胺衍生物是布雷肯肽B1拮抗剂或逆向激动剂，在治疗或预防与布雷肯肽B1途径相关的疼痛和炎症症状方面很有用。R2a从（1）Ra组中选择。 （2）（CH2）nNRbC（O）Ra。（3）（CH2）nNRbSO2Rd。（4）（CH2）nNRbCO2Ra。（5）（CH2）k-杂环，可选择地取代为1到3个独立选择的卤素，硝基，氰基，ORa，SRa，C1-4烷基和C1-3卤代烷基，其中所述杂环是（a）具有N，O和S中选择的环杂原子的5元杂芳环，并且可选地具有多达3个额外的环氮原子，其中所述环可选地与苯融合；或（b）含有1到3个环氮原子和其N-氧化物的6元杂芳环。其中所述环可选地与苯融合。（6）（CH2）kCO2Ra和（7）（CH2）C（O）NRbRc。 R2b是OH或从R2a选择的组；或R2a和R2b与它们连接的碳原子一起形成一个3到7个成员的碳环，可选择地取代为1到4个独立选择的卤素，ORa，C1-4烷基和C1-4卤代烷基；

  公开号：

  WO2005063690A1

文献信息

• N-biarylmethyl aminocycloalkanecarboxamide derivatives
  申请人：Kuduk D. Scott

  公开号：US20050288305A1

  公开（公告）日：2005-12-29

  N-Biarylmethylainocycloalkanecarboxamide derivatives are bradykinin B1 antagonists or inverse agonists useful in the treatment or prevention of symptoms such as pain and inflammation associated with the bradykinin B1 pathway.

  N-双芳基甲基氨基环烷基羧酰胺衍生物是Bradykinin B1拮抗剂或反向激动剂，可用于治疗或预防与Bradykinin B1通路相关的疼痛和炎症等症状。
• Alpha-Hydroxy Amides as Bradykinin Antagonists or Inverse Agonists
  申请人：Wood Michael R.

  公开号：US20080318976A1

  公开（公告）日：2008-12-25

  α-Hydroxy amide derivatives of the general formula (I) are bradykinin B1 antagonists or inverse agonists useful in the treatment or prevention of symptoms such as pain and inflammation associated with the bradykinin B1 pathway. R 2a is selected from (1) a group selected from R a . (2)(CH 2 ) n NR b C(O)R a . (3)(CH 2 ) n NR b SO 2 R d . (4)(CH 2 ) n NR b CO 2 R a .(5)(CH 2 ) k -heterocycle optionally substituted with 1 to 3 groups independently selected from halogen.nitro, cyano.OR a .SR a .C 1-4 alkyl and C 1-3 haloakyl wherein said heterocycle is (a) a 5-membered heteroaromatic ring having a ring heteroatom selected from N.O and S. and optionally having up to 3 additional ring nitrogen atoms wherein said ring is optionally benzo-fused; or (b) a 6-membered heteromatic ring containing from 1 to 3 ring nitrogen atoms and N-oxydes thereof. Wherein said ring is optionally benzo-fused. (6)(CH 2 ) k CO 2 R a . and (7)(CH 2 )C(O)NR b R c . R 2b is OH or a group selected from R 2a ; or R 2a and R 2b together with the carbon atom to which they are attached form a 3- to 7-membered carbocyclic ring optionally substituted with 1 to 4 groups independently selected from halogen. OR a . C 1-4 alkyl and C 1-4 haloalkyl;

  通式（I）的α-羟基酰胺衍生物是Bradykinin B1拮抗剂或逆激动剂，可用于治疗或预防与Bradykinin B1途径相关的疼痛和炎症等症状。其中R2为以下之一：（1）从Ra选择的一组；（2）（CH2）nNRbC（O）Ra；（3）（CH2）nNRbSO2Rd；（4）（CH2）nNRbCO2Ra；（5）（CH2）k-杂环，可选地取代1-3个独立选择的卤素、硝基、氰基、ORa、SRa、C1-4烷基和C1-3卤代烷基，其中所述杂环为（a）具有从N、O和S中选择的环杂原子的5元杂芳环，并且可选地具有多达3个额外的环氮原子，其中所述环可选地与苯并联；或（b）含有1-3个环氮原子和其N-氧化物的6元杂芳环。其中所述环可选地与苯并联；（6）（CH2）kCO2Ra；和（7）（CH2）C（O）NRbRc。R2b为OH或从R2a选择的一组；或R2a和R2b一起与它们连接的碳原子形成一个3-7成员的碳环，可选地取代1-4个独立选择的卤素、ORa、C1-4烷基和C1-4卤代烷基。
• Alpha-hydroxy amides as bradykinin antagonists or inverse agonists
  申请人：Merck Sharp & Dohme Corp.

  公开号：US07790754B2

  公开（公告）日：2010-09-07

  α-Hydroxy amide derivatives of the general formula (I) are bradykinin B1 antagonists or inverse agonists useful in the treatment or prevention of symptoms such as pain and inflammation associated with the bradykinin B1 pathway. R2a is selected from (1) a group selected from Ra. (2) (CH2)nNRbC(O)Ra. (3) (CH2)nNRbSO2Rd. (4) (CH2)nNRbCO2Ra. (5) (CH2)k-heterocycle optionally substituted with 1 to 3 groups independently selected from halogen.nitro, cyano.ORa.SRa.C1-4 alkyl and C1-3 haloakyl wherein said heterocycle is (a) a 5-membered heteroaromatic ring having a ring heteroatom selected from N.O and S. and optionally having up to 3 additional ring nitrogen atoms wherein said ring is optionally benzo-fused; or (b) a 6-membered heteromatic ring containing from 1 to 3 ring nitrogen atoms and N-oxydes thereof. Wherein said ring is optionally benzo-fused. (6) (CH2)kCO2Ra. and (7) (CH2)C(O)NRbRc. R2b is OH or a group selected from R2a; or R2a and R2b together with the carbon atom to which they are attached form a 3- to 7-membered carbocyclic ring optionally substituted with 1 to 4 groups independently selected from halogen. ORa. C1-4 alkyl and C1-4 haloalkyl.

  通式（I）的α-羟基酰胺衍生物是布雷地酮B1拮抗剂或逆激动剂，可用于治疗或预防与布雷地酮B1通路相关的疼痛和炎症等症状。其中，R2a选自（1）Ra选自的一组；（2）（CH2）nNRbC（O）Ra；（3）（CH2）nNRbSO2Rd；（4）（CH2）nNRbCO2Ra；（5）（CH2）k-杂环，可选地被1至3个独立选择的卤素、硝基、氰基、ORa、SRa、C1-4烷基和C1-3卤代烷基取代，其中所述杂环是（a）一个5-成员杂芳环，具有从N、O和S中选择的杂环原子，并可选地具有多达3个额外的环氮原子，其中所述环可选地与苯融合；或（b）一个6-成员杂环，含有1至3个环氮原子和其N-氧化物。其中所述环可选地与苯融合；（6）（CH2）kCO2Ra；以及（7）（CH2）C（O）NRbRc。R2b是OH或选自R2a的一组；或者R2a和R2b与它们连接的碳原子一起形成一个3至7成员的碳环，可选地被1至4个独立选择的卤素、ORa、C1-4烷基和C1-4卤代烷基取代。
• Synthesis, biological evaluation of chrysin derivatives as potential immunosuppressive agents
  作者：Peng-Cheng Lv、Tian-Tian Cai、Yong Qian、Juan Sun、Hai-Liang Zhu

  DOI：10.1016/j.ejmech.2010.10.034

  日期：2011.1

  A series of novel chrysin derivatives was firstly synthesized and evaluated on their immunosuppressive activity in the search for potential immunosuppressive agents. Among them, compounds 5c displayed the most potent immunosuppressive inhibitory activity with IC50 of 0.78 mu M, which was comparable to that of cyclosporin A (IC50 = 0.06 mu M). The preliminary mechanism of compound 5c inhibition effects was also detected by flow cytometry (FCM), and the compound exerted immunosuppressive activity via inducing the apoptosis of activated lymph node cells in a dose dependent manner. Furthermore, the estimated LD50 (in mg/kg) in vivo of compound 5c is 738.2, which indicated that compound 5c was low toxic. (C) 2010 Elsevier Masson SAS. All rights reserved.
• N-BIARYLMETHYL AMINOCYCLOALKANECARBOXAMIDE DERIVATIVES
  申请人：Merck & Co., Inc.

  公开号：EP1545538A2

  公开（公告）日：2005-06-29