S-homoallyl-C | 199807-41-5

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: S-homoallyl-C
• 英文别名: S-(3-butenyl)-L-cysteine；(2R)-2-amino-3-but-3-enylsulfanylpropanoic acid
• CAS: 199807-41-5
• 化学式: C₇H₁₃NO₂S
• 分子量: 175.252
• InChiKey: AXMNNFIHFNGRNW-LURJTMIESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -1.6
• 重原子数：
  11
• 可旋转键数：
  6
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.57
• 拓扑面积：
  88.6
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  S-homoallyl-C 在 氯化亚砜 、 三乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 24.5h， 生成
  参考文献：
  名称：

  Structure-activity relationship study and biological evaluation of SAC-Garlic acid conjugates as novel anti-inflammatory agents

  摘要：

  A series of S-allyl-L-cysteine (SAC) with garlic acid conjugates as anti-inflammatory agents were designed and synthesized. Among the 40 tested compounds, SMU-8c exhibited the most potent inhibitory activity to Pam(3)CSK(4)-induced nitric oxide (NO) in RAW264.7 macrophages with IC50 of 22.54 +/- 2.60 mu M. The structure-activity relationship (SAR) study suggested that the esterified carboxyl group, carbon chain extension and methoxylation phenol hydroxy could improve the anti-inflammatory efficacy. Preliminary anti-inflammatory mechanism studies showed that SMU-8c significantly down-regulated the levels of Pam(3)CSK(4) triggered TNF-alpha cytokine in human THP-1 cells, mouse RAW 264.7 macrophages, as well as in ex-vivo human peripheral blood mononuclear cells (PBMC) with no influence on cell viability. SMU-8c specifically blocked the Pam(3)CSK(4) ignited secreted embryonic alkaline phosphatase (SEAP) signaling with no influence to Poly I:C or LPS triggered TLR3 or TLR4 signaling. Moreover, SMU-8c suppressed TLR2 in HEK-Blue hTLR2 cells and inhibited the formation of TLR1-TLR2, and TLR2-TLR6 complex in human PBMC. In summary, SMU-8c inhibited the TLR2 signaling pathway to down-regulate the inflammation cytokines, such as NO, SEAP and TNF-alpha, to realize its anti-inflammatory activity. (C) 2019 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2019.06.059
• 作为产物：
  描述：

  4-溴-1-丁烯 、 L-半胱氨酸盐酸盐无水物 在 氨 作用下， 以 乙醇 、 水 为溶剂， 反应 20.0h， 生成 S-homoallyl-C
  参考文献：
  名称：

  Influence of α-methylation in constructing stapled peptides with olefin metathesis

  摘要：

  Ring-closing metathesis is commonly utilized in peptide macro-cyclization. The influence of alpha-methylation of the amino acids bearing the olefin moieties has never been systematically studied. In this report, controlled reactions unambiguously indicate that alpha-methylation at the N-terminus of the metathesis sites is crucial for this reaction to occur. Also, we first elucidated that the E-isomers of stapled peptides are significantly more helical than the Z-isomers. (C) 2014 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2014.08.004

文献信息

• REMEDIES FOR BRAIN DISEASES
  申请人：WAKUNAGA PHARMACEUTICAL CO., LTD.

  公开号：EP0885608A1

  公开（公告）日：1998-12-23

  The present invention discloses the use, in the manufacture of a preventive and therapeutic drug of a brain disease, of a compound represented by formula (1):         CH2=CH-CH2-S(O)n-R     (1) [wherein R represents a hydrogen atom, an alkyl group, an alkenyl group, a substituted alkyl group, a substituted alkenyl group, an alkylthio group, an alkenylthio group, a phenyl group, a substituted phenyl group, a heterocyclic group, or a group derived from an amino acid or an oligopeptide by deletion of one hydrogen atom, and which group may have a protective group; and n is 0, 1, or 2], a glycoside thereof, or a salt of the compound or the glycoside. The drug of the present invention for ameliorating brain diseases, inhibiting reduction of brain neurons and promoting branching of neurites, is useful for the prevention and treatment of brain diseases such as dementia in association with degeneration and sloughing of brain neurons.

  本发明公开了式 (1) 所代表的化合物在制造脑疾病预防和治疗药物中的用途： CH2=CH-CH2-S(O)n-R (1) [其中 R 代表氢原子、烷基、烯基、取代的烷基、取代的烯基、烷硫基、烯硫基、苯基、取代的苯基、杂环基、或由氨基酸或低聚肽去掉一个氢原子衍生的基团，该基团可带有保护基；且 n 为 0、1 或 2]、其糖苷或该化合物或该糖苷的盐。 本发明用于改善脑部疾病、抑制脑神经元减少和促进神经元分支的药物可用于预防和治疗与脑神经元变性和脱落有关的痴呆等脑部疾病。
• IMMUNOREGULATOR
  申请人：WAKUNAGA PHARMACEUTICAL CO., LTD.

  公开号：EP3228312A1

  公开（公告）日：2017-10-11

  An immunomodulator useful for modulating immune function and maintaining intravital homeostasis is provided. The immunomodulator comprises S-1-propenycysteine or a salt thereof as an active ingredient.

  本研究提供了一种用于调节免疫功能和维持体内平衡的免疫调节剂。该免疫调节剂的活性成分包括 S-1-丙半胱氨酸或其盐类。
• BLOOD PRESSURE-LOWERING AGENT
  申请人：Wakunaga Pharmaceutical Co., Ltd.

  公开号：EP3308781A1

  公开（公告）日：2018-04-18

  Provided is an antihypertensive agent that is safe and has a mild effect. An antihypertensive agent comprising S-1-propenylcysteine or a salt thereof as an active ingredient.

  本研究提供了一种安全且作用温和的降压药。 一种由 S-1-丙烯基半胱氨酸或其盐作为活性成分的降压药。
• BLOOD FLOW IMPROVER
  申请人：Wakunaga Pharmaceutical Co., Ltd.

  公开号：EP3666269A1

  公开（公告）日：2020-06-17

  Provided is a blood flow improver which is safe and has a mild action. The blood flow improver comprises S-1-propenylcysteine or a salt thereof as an active ingredient.

  本文提供了一种安全且作用温和的血流促进剂。该血流促进剂的活性成分包括 S-1-丙烯基半胱氨酸或其盐类。
• AUTOPHAGY ACTIVATING AGENT
  申请人：Wakunaga Pharmaceutical Co., Ltd.

  公开号：EP3804709A1

  公开（公告）日：2021-04-14

  To provide a compound used for activating autophagy, which has few side effects and mild effects. An autophagy activating agent comprising S1PC or a salt thereof as an active ingredient.

  提供一种用于激活自噬的化合物，其副作用小且效果温和。 一种自噬激活剂，其活性成分包括 S1PC 或其盐。