3-(N-piperidinyl)methylbenzoic acid

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 哌啶类
• 英文名称: 3-(N-piperidinyl)methylbenzoic acid
• 英文别名: 3-(1-piperidinomethyl)benzoic acid；3-(Piperidin-1-ium-1-ylmethyl)benzoate
• 化学式: C₁₃H₁₇NO₂
• mdl: MFCD05841589
• 分子量: 219.283
• InChiKey: UIXWGRXBYZGOQK-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.8
• 重原子数：
  16
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.461
• 拓扑面积：
  40.5
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  3-(N-piperidinyl)methylbenzoic acid 在 氯化亚砜 作用下， 反应 1.0h， 生成 3-(Piperidin-1-ylmethyl)benzoyl chloride
  参考文献：
  名称：

  Discovery and Structural Optimization of 4-(Aminomethyl)benzamides as Potent Entry Inhibitors of Ebola and Marburg Virus Infections

  摘要：

  The recent Ebola epidemics in West Africa underscore the great need for effective and practical therapies for future Ebola virus outbreaks. We have discovered a new series of remarkably potent small molecule inhibitors of Ebola virus entry. These 4-(aminomethyl)benzamide-based inhibitors are also effective against Marburg virus. Synthetic routes to these compounds allowed for the preparation of a wide variety of structures, including a conformationally restrained subset of indolines (compounds 41-50). Compounds 20, 23, 32, 33, and 35 are superior inhibitors of Ebola (Mayinga) and Marburg (Angola) infectious viruses. Representative compounds (20, 32, and 35) have shown good metabolic stability in plasma and liver microsomes (rat and human), and 32 did not inhibit CYP3A4 nor CYP2C9. These 4-(aminomethyl)benzamides are suitable for further optimization as inhibitors of filovirus entry, with the potential to be developed as therapeutic agents for the treatment and control of Ebola virus infections.

  DOI：

  10.1021/acs.jmedchem.0c00463
• 作为产物：
  描述：

  3-(溴甲基)苯甲酸甲酯 在 水 、 sodium hydroxide 作用下， 以 甲醇 、 乙酸乙酯 为溶剂， 反应 1.5h， 生成 3-(N-piperidinyl)methylbenzoic acid
  参考文献：
  名称：

  通过分子对接和分子动力学模拟发现高效 CRBN 配体并深入了解它们的结合模式

  摘要：

  PROTACs和分子胶的蓬勃发展，其发展离不开E3泛素连接酶配体。在本文中，设计并合成了两个系列的 CRBN 配体。并且三种化合物表现出比来那度胺高约 13 倍的 CRBN 结合亲和力。同时，进行了分子对接和分子动力学模拟，以深入了解这些新型配体对CRBN的结合模型。

  DOI：

  10.1002/cmdc.202200573

文献信息

• Thiadiazoleamide derivative and anti-ulcer drug
  申请人：Shiseido Co., Ltd.

  公开号：US05912258A1

  公开（公告）日：1999-06-15

  A thiadiazoleamide derivative or a salt thereof expressed by the following Formula 1: ##STR1## wherein each of R.sub.1 and R.sub.2 represents a hydrogen atom, a lower alkyl group, a lower alkoxy group, a lower alkylamino group or an alkenyloxy group; wherein when either R.sub.1 or R.sub.2 is a hydrogen atom, the other is not a hydrogen atom; R.sub.3 represents a lower alkyl group, an aryl group, a pyridyl group or --N(R.sub.4)R.sub.5, wherein R.sub.4 and R.sub.5 represent lower alkyl groups or together represent a saturated heterocyclic ring having 4-8 members; wherein when R.sub.1 or R.sub.2 is a lower alkoxy group, R.sub.3 is --N(R.sub.4)R.sub.5 or a pyridyl group; and n represents an integer of 1-3. The derivatives have anti-ulcer effect to be available for preventing or curing ulcers in mammals.

  一种由以下化学式1表示的噻二唑酰胺衍生物或其盐：##STR1## 其中R.sub.1和R.sub.2中的每一个代表氢原子、较低的烷基基团、较低的烷氧基团、较低的烷基氨基团或烯氧基团；其中当R.sub.1或R.sub.2中的一个是氢原子时，另一个不是氢原子；R.sub.3代表较低的烷基基团、芳基、吡啶基或--N(R.sub.4)R.sub.5，其中R.sub.4和R.sub.5代表较低的烷基基团或一起代表具有4-8个成员的饱和杂环环；其中当R.sub.1或R.sub.2是较低的烷氧基团时，R.sub.3是--N(R.sub.4)R.sub.5或吡啶基；n代表1-3的整数。这些衍生物具有抗溃疡作用，可用于预防或治疗哺乳动物的溃疡。
• Heterocyclic Compounds as CCR2 Antagonists
  申请人：Bower Justin Fairfield

  公开号：US20120264762A1

  公开（公告）日：2012-10-18

  Compounds of formula (I) Q-L-W—C(═X)—Z—P wherein Q is an amine of the formula —N(R 1 )(R 2 ); L is an alkyl or heterocyclyl-alkyl linker; W is a 6- or 7-membered aliphatic ring comprising ring atoms Y 1 and Y 2 which are linked to groups L and C(X) respectively and Y 1 and Y 2 are independently selected from N and C; X is O, N, N—CN or S; Z is NR 3 ; P is an optionally substituted monocyclic or bicyclic aryl or heteroaryl group; and pharmaceutically acceptable salts or solvates thereof, are useful in the treatment of C—C chemokine mediated conditions.

  化合物的式子为(I)Q-L-W—C(═X)—Z—P，其中Q是公式—N(R1)(R2)的胺基；L是烷基或杂环烷基-烷基连接物；W是一个6-或7-成员的脂肪环，包括环原子Y1和Y2，它们分别与基团L和C(X)相连，Y1和Y2独立地选自N和C；X是O、N、N—CN或S；Z是NR3；P是一个可选择取代的单环或双环芳基或杂芳基基团；以及其药学上可接受的盐或溶剂，用于治疗C-C趋化因子介导的疾病。
• Alkylenediamine derivative, anti-ulcer drug, and antibacterial drug
  申请人：SHISEIDO COMPANY LIMITED

  公开号：EP0875501A2

  公开（公告）日：1998-11-04

  An alkylenediamine derivative or a salt thereof expressed by the following formula 1: wherein each of R1 and R2 represents a lower alkyl group, and W represents a group expressed by any of the following formulas 2 to 4; wherein R3 is an alkenyl group; R4 is a lower alkyl group, a lower alkoxy group, or a halogen atom; X is a group expressed by -O-, -S-, or -N(R5)-, while R5 is hydrogen atom, a lower alkyl group, or an alkenyl group; Y is carbon or nitrogen atom; m is an integer of 1 to 3; n is an integer of 0 to 2; R6 is a lower alkyl group; R7 is hydroxy or benzyloxy group; R8 is a lower alkyl, a lower alkoxy, a piperidinoalkyl, a substituted carbamoyl, or a substituted amino group; and l is 1 or 2. The alkylenediamine derivative has an anti- ulcer effect or an antibacterial activity against Helicobacter pyroli, and has also high safety to be available for prevention or cure of ulcers.

  由下式 1 表示的烷基二胺衍生物或其盐： 其中 R1 和 R2 各代表一个低级烷基，W 代表由下式 2 至 4 中的任何一个所表示的基团； 其中 R3 是烯基 R4 是低级烷基、低级烷氧基或卤原子； X是由-O-、-S-或-N(R5)-表示的基团，而R5是氢原子、低级烷基或烯基； Y 是碳原子或氮原子； m 是 1 至 3 的整数； n 是 0 至 2 的整数； R6 是低级烷基 R7 是羟基或苄氧基； R8 是低级烷基、低级烷氧基、哌啶烷基、取代的氨基甲酰基或取代的氨基；以及 l 是 1 或 2。 烷基二胺衍生物具有抗溃疡作用或对焦螺旋杆菌的抗菌活性，而且安全性高，可用于预防或治疗溃疡。
• Benzamide derivatives for inhibiting endoplasmic reticulum (ER) stress
  申请人：The Board of Regents of the University of Oklahoma

  公开号：US11203582B2

  公开（公告）日：2021-12-21

  Novel 3-(N-piperidinyl)methyl benzamide derivatives are disclosed. The compounds can be used in treating diseases and conditions which are associated with abnormal cell function related to endoplasmic reticulum (ER) stress. For example, the compounds can be used as suppressors of ER stress-induced pancreatic β-cell dysfunction and death, for example in the treatment of diabetes.

  新型3-(N-哌啶基)甲基苯甲酰胺衍生物被披露。这些化合物可用于治疗与内质网(ER)应激相关的异常细胞功能相关的疾病和病症。例如，这些化合物可作为ER应激诱导的胰腺β细胞功能障碍和死亡的抑制剂，例如在治疗糖尿病中使用。
• IL-6 inhibitors and methods of treatment
  申请人：University of Florida Research Foundation, Incorporated

  公开号：US11530181B2

  公开（公告）日：2022-12-20

  The instant invention describes compounds having IL-6 modulating activity, and methods of treating diseases, disorders or symptoms thereof mediated by IL-6.

  本发明描述了具有 IL-6 调节活性的化合物，以及治疗由 IL-6 介导的疾病、失调或症状的方法。