(4-(4-氯苯氧基)苯基)甲胺盐酸盐 | 262862-71-5

• 物质功能分类: 医药中间体 - 杂环化合物
• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 中文名称: (4-(4-氯苯氧基)苯基)甲胺盐酸盐
• 英文名称: 4-(4-chlorophenoxy)benzylamine hydrochloride
• 英文别名: (4-(4-chlorophenoxy)phenyl)methanamine hydrochloride；[4-(4-chlorophenoxy)phenyl]methanamine;hydrochloride
• CAS: 262862-71-5
• 化学式: C₁₃H₁₂ClNO*ClH
• 分子量: 270.158
• InChiKey: BFQVELFTOFIOEB-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.01
• 重原子数：
  17
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.08
• 拓扑面积：
  35.2
• 氢给体数：
  2
• 氢受体数：
  2

安全信息

• 危险等级：
  IRRITANT
• 海关编码：
  2922299090
• 危险性防范说明：
  P261,P305+P351+P338
• 危险性描述：
  H315,H319,H335

制备方法与用途

应用(4-(4-氯苯氧基)苯基)甲胺盐酸盐是一种医药中间体。文献报道显示，它可用于制备一种咪唑并[1,2-a]吡啶衍生物，如N-(4-(4-氯苯氧基)苄基)-2,7-二甲基咪唑并[1,2-a]吡啶-3-甲酰胺。该化合物具有抑制结核分枝杆菌的作用。

反应信息

• 作为反应物：
  描述：

  (4-(4-氯苯氧基)苯基)甲胺盐酸盐 、 5-乙基-2-甲基-2H-吡唑-3-甲酸 在 N-羟基-7-氮杂苯并三氮唑 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 、 三乙胺 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 以58%的产率得到N-(4-(4-chlorophenoxy)benzyl)-3-ethyl-1-methyl-1H-pyrazole-5-carboxamide
  参考文献：
  名称：

  Structure–Activity Relationship Studies of Tolfenpyrad Reveal Subnanomolar Inhibitors ofHaemonchus contortusDevelopment

  摘要：

  Recently, we have discovered that the registered pesticide, tolfenpyrad, unexpectedly and potently inhibits the development of the L4 larval stage of the parasitic nematode Haemonchus contortus with an IC50 value of 0.03 mu M while displaying good selectivity, with an IC50 of 37.9 mu M for cytotoxicity. As a promising molecular template for medicinal chemistry optimization, we undertook anthelmintic structure-activity relationships for this chemical. Modifications of the left-hand side (LHS), right-hand side (RHS), and middle section of the scaffold were explored to produce a set of 57 analogues. Analogues 25, 29, and 33 were shown to be the most potent compounds of the series, with IC50 values at a subnanomolar level of potency against the chemotherapeutically relevant fourth larval (L4) stage of H. contortus. Selected compounds from the series also showed promising activity against a panel of other different parasitic nematodes, such as hookworms and whipworms.

  DOI：

  10.1021/acs.jmedchem.8b01789

文献信息

• NOVEL THIOL DERIVATIVES, PROCESS FOR PRODUCING THE SAME AND UTILIZATION THEREOF
  申请人：Takeda Chemical Industries, Ltd.

  公开号：EP1132379A1

  公开（公告）日：2001-09-12

  The present invention provides a compound represented by Formula: wherein ring A and ring B may be same or different and each is an optionally substituted homocyclic or heterocyclic ring and the like, each R1 may be same or different and is a hydrogen atom, an optionally substituted hydrocarbon group, an acyl group, an optionally substituted heterocyclic group or SR2, etc., X1 is a bond, an optionally substituted divalent C1-3 aliphatic hydrocarbon group or -NR3-, etc, X2 is a bond, an optionally substituted divalent C1-3 aliphatic hydrocarbon group, -NR4-, -O- or -S(O)p-(wherein p is 0, 1 or 2), each Y may be same or different and is a hydrogen atom, an optionally substituted hydrocarbon group, a halogen atom, a carboxyl group, an acyl group, an optionally substituted hydroxy group, an optionally substituted amino group, SR5, an oxo group, a thioxo group, an optionally substituted imino group, a nitro group, a cyano group, etc., each m may be same or different and is 0 or 1, n is an integer of 1 to 3, q1 is an integer of 1 to 2n+4, q2 is an integer of 0 to 2n+3, and the sum of q1 and q2 is 2n+4 or a salt thereof.

  本发明提供了一种由式表示的化合物： 其中，环 A 和环 B 可以相同或不同，并且各自是任选取代的同环或杂环等，每个 R1 可以相同或不同，并且是氢原子、任选取代的烃基、酰基、任选取代的杂环基团或 SR2 等、X1 是键、任选取代的二价 C1-3 脂肪族烃基或-NR3-等，X2 是键、任选取代的二价 C1-3 脂肪族烃基、-NR4-、-O-或-S(O)p-（其中 p 为 0、1 或 2），每个 Y 可以相同或不同，并且是氢原子、任选取代的烃基、卤素原子、羧基、酰基、任选取代的羟基、任选取代的氨基、SR5、氧代基团、硫代基团、任选取代的亚氨基、硝基、氰基等。,每个 m 可以相同或不同，且为 0 或 1，n 为 1 至 3 的整数，q1 为 1 至 2n+4 的整数，q2 为 0 至 2n+3 的整数，且 q1 和 q2 之和为 2n+4 或其盐。
• Thiol compounds, their production and use
  申请人：——

  公开号：US20030078253A1

  公开（公告）日：2003-04-24

  The present invention provides a compound represented by Formula: 1 wherein ring A and ring B may be same or different and each is an optionally substituted homocyclic or heterocyclic ring and the like, each R 1 may be same or different and is a hydrogen atom, an optionally substituted hydrocarbon group, an acyl group, an optionally substituted heterocyclic group or SR 2 , etc., X is a bond, an optionally substituted divalent C 1-3 aliphatic hydrocarbon group or —NR 3 —, etc, X 2 is a bond, an optionally substituted divalent C 1-3 aliphatic hydrocarbon group, —NR 4 —, —O— or —S(O) p — (wherein p is 0, 1 or 2), each Y may be same or different and is a hydrogen atom, an optionally substituted hydrocarbon group, a halogen atom, a carboxyl group, an acyl group, an optionally substituted hydroxy group, an optionally substituted amino group, SR 5 , an oxo group, a thioxo group, an optionally substituted imino group, a nitro group, a cyano group, etc., each m may be same or different and is 0 or 1, n is an integer of 1 to 3, q 1 is an integer of 1 to 2 n +4, q 2 is an integer of 0 to 2 n +3, and the sum of q 1 and q 2 is 2 n +4 or a salt thereof.

  本发明提供了一种由式表示的化合物： 1 其中，环 A 和环 B 可以相同或不同，且各自为任选取代的同环或杂环等，每个 R 1 可以相同或不同，并且是氢原子、任选取代的烃基、酰基、任选取代的杂环基团或 SR 2 等，X 是键、任选取代的二价 C 1-3 脂族烃基或-NR 3 -等，X 2 是键、任选取代的二价 C 1-3 脂族烃基、-NR 4 -、-O- 或 -S(O) p - 其中 p 为 0、1 或 2），每个 Y 可以相同或不同，并且是氢原子、任选取代的烃基、卤素原子、羧基、酰基、任选取代的羟基、任选取代的氨基、SR 5 、氧代基团、硫代基团、任选取代的亚氨基、硝基、氰基等，每个 m 可以相同或不同且为 0 或 1，n 为 1 至 3 的整数，q 1 是 1 至 2 的整数 n +4, q 2 是 0 到 2 的整数 n 加;3，而 q 1 和 q 2 为 2 n +4或其盐。
• Advancement of Imidazo[1,2-<i>a</i>]pyridines with Improved Pharmacokinetics and nM Activity vs. <i>Mycobacterium tuberculosis</i>
  作者：Garrett C. Moraski、Lowell D. Markley、Jeffrey Cramer、Philip A. Hipskind、Helena Boshoff、Mai A. Bailey、Torey Alling、Juliane Ollinger、Tanya Parish、Marvin J. Miller

  DOI：10.1021/ml400088y

  日期：2013.7.11

  A set of 14 imidazo[1,2-a]pyridine-3-carboxamides was synthesized and screened against Mycobacterium tuberculosis H(37)Rv. The minimum inhibitory concentrations of 12 of these agents were <= 1 mu M against replicating bacteria and 5 compounds (9, 12, 16, 17, and 18) had MIC values <= 0.006 mu M. Compounds 13 and 18 were screened against a panel of MDR and XDR drug resistant clinical Mtb strains with the potency of 18 surpassing that of clinical candidate PA-824 by nearly 10-fold. The in vivo pharmacokinetics of compounds 13 and 18 were evaluated in male mice by oral (PO) and intravenous (IV) routes. These results indicate that readily synthesized imidazo[1,2-a]pyridine-3-carboxamides are an exciting new class of potent, selective anti-TB agents that merit additional development opportunities.
• US6420415B1
  申请人：——

  公开号：US6420415B1

  公开（公告）日：2002-07-16
• US6699881B2
  申请人：——

  公开号：US6699881B2

  公开（公告）日：2004-03-02